Chicago Outfit

The early years of organized crime in Chicago, in the late 19th and early 20th centuries, were marked by the division of various street gangs controlling the South Side and North Side, as well as the Black Hand organizations of Little Italy. In later years, the Outfit consisted of various street crews controlling different territories around Chicago including Elmwood Park, Melrose Park, Chicago Heights, Rush Street, Grand Avenue and Chinatown.

Big Jim Colosimo centralized control in the early 20th century. Colosimo was born in Calabria, Italy, in 1878, and immigrated to Chicago in 1895, where he established himself as a criminal. By 1909, with the help of bringing Johnny Torrio from New York to Chicago, he was successful enough that he was encroaching on the criminal activity of the Black Hand organization.{{cite book|last=Binder|first=John|title=The Chicago Outfit|year=2003|publisher=Arcadia Publishing|isbn=0738523267|page=9}}{{cite web|title=When the Outfit Ran Chicago, Vol I:The "Big Jim" Colosimo Era|url=https://www.dr.com.tr/ekitap/when-the-outfit-ran-chicago-vol-i-the-big-jim-colosimo-era|website=D&R|access-date=10 December 2018|language=tr}} Colosimo also "cultivated deep political connections" after "serving as a precinct captain in the organization of First Ward Alderman Couglin and Kenna, and later [became] the bagman (collector of illegal profits and dispenser of bribes) in the vice-laden Levee District, which afforded him with blanket political protection".{{Cite journal |last1=Binder |first1=John J. |last2=Lurigio |first2=Arthur J. |date=May 2013 |title=Introduction to the Special Issue—The Rise and Fall of Chicago's Organized Crime Family |url=https://doi.org/10.1177/1043986213485645 |journal=Journal of Contemporary Criminal Justice |volume=29 |issue=2 |pages=184–197 |doi=10.1177/1043986213485645 |s2cid=147451284 |issn=1043-9862|url-access=subscription }}

When Prohibition went into effect in 1920, Torrio pushed for the gang to enter into bootlegging, but Colosimo stubbornly refused. In March 1920, Colosimo secured an uncontested divorce from his wife, Victoria Moresco.{{cite web|url=https://www.chicagotribune.com/news/ct-xpm-1987-07-26-8702250077-story.html|title=The Vice Lord Who Fell in Love With a Choir Singer|publisher=chicagotribune.com|date=July 26, 1987}} A month later, he and singer Dale Winter eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side. On May 11, 1920, Colosimo was killed by a gunman waiting in the coat room of his restaurant, Colosimo's cafe. The killer was most likely Frankie Yale, fulfilling a contract commissioned by Johnny Torrio.{{cite book|last=Binder |first=John J.|year=2017 |title=Al Capone's Beer Wars: A Complete History of Organized Crime in Chicago during Prohibition|publisher=Prometheus|isbn=978-1633882850}}

Torrio's organization was made up predominately of ethnic Italians but had a large contingent of members from other immigrant backgrounds. Torrio's gang also differed from the other Chicago gangs by recruiting from New York's underworld, regularly welcoming that city's ambitious criminals into his organization's ranks. Alphonse Capone had left New York for Chicago in 1919, likely under orders from mob boss Frankie Yale to leave town to avoid retaliation for previous violence they had committed in New York. Capone began in Chicago as a doorman at the Four Deuces club. By 1924, Capone's business acumen and shrewd intelligence had gained him a place as Torrio's right-hand man. Many rivals saw Capone as responsible for the proliferation of brothels in the city.Sifakis, Carl, The Mafia Encyclopedia, 2nd ed., Checkmark Books (1999), p.362Russo, Gus, The Outfit, Bloomsbury (2001), pp.39,40Disasters and Tragic Events, edited by Mitchell Newton-Matza p.258

In 1923, William Dever was elected mayor of Chicago, and he began to crack down on Torrio's underworld activities within the city. Losing their political cover, the gang looked to the suburbs for a new base of operations. Torrio ordered Capone to lead a takeover of the town of Cicero, where he was able to corrupt city manager Joseph Z. Klenha. The gang set up dozens of brothels, speakeasies, gambling dens, and other businesses within the town. On April 1, 1924, Cicero municipal elections were threatening Kenha's leadership. Kenha appealed to Torrio and Capone for their support, which they responded to by terrorizing the opposition and voting public on election day. The gang guarded polling places, ensuring people knew the right way to vote and violently preventing entry to those who did not. They ransacked the local Democratic party campaign headquarters, forcibly detaining the election workers for hours. By that afternoon, the Chicago Police Department was ordered to step in to halt the violence by Cook County Judge Edmund J. Jareki. Seventy plainclothes officers, newly deputized as county sheriffs, descended on Cicero. Frank Capone, Al's brother, was killed that evening by detective sergeant William Cusack during an altercation on 22nd Street and Cicero Avenue. Charles Fischetti was also arrested at the scene. Kenha won the election, ensuring the Torrio-Capone gang's local immunity into the 1930s.

Torrio was wary of being drawn into gang wars and tried to negotiate agreements over territory between rival crime groups. The smaller North Side Gang led by Dean O'Banion was of mixed ethnicity, and it came under pressure from the Genna brothers who were allied with Torrio. O'Banion found that Torrio was unhelpful with the encroachment of the Gennas into the North Side, despite his pretensions to be a settler of disputes.{{cite book |title= Capone: The Man and the Era|url= https://archive.org/details/caponemanera00berg|url-access= registration|last= Bergreen|first= Laurence|year= 1994|publisher= Simon and Schuster Paperbacks|location= New York|isbn= 978-0-684-82447-5|pages= [https://archive.org/details/caponemanera00berg/page/131 131–132]}} The "Terrible" Genna brothers, as they were known, consisted of Peter, James, Angelo, Tony, Sam and Mike "The Devil" Genna. They were known for their ruthlessness and intemperate disposition.{{Cite book|last=Lindberg|first=Richard|title=Gangland Chicago; Criminality And Lawlessness In The Windy City|publisher=Rowman & Littlefield|year=2016|isbn=9781442231955|location=Lanham, Maryland|pages=247–248}} In a fateful step, Torrio either arranged for or acquiesced to the murder of O'Banion at his flower shop on November 10, 1924. This placed Hymie Weiss at the head of the gang, backed by Vincent Drucci and Bugs Moran. Weiss had been a close friend of O'Banion and the North Siders made it a priority to get revenge on his killers.Bergreen, pp 134–135Bergreen, p. 138{{cite web|url=http://www.myalcaponemuseum.com/id89.htm|title=Hymie Weiss|website=Myalcaponemuseum.com|access-date=2 October 2018}}

At the end of 1924, the Torrio-Capone gang had between 300–400 members, while the North Side gang could count on around 200 soldiers.

File:Al Capone in 1929.jpg]]

In early 1925, the North Side began a string of retaliations for O'Banion's murder. First, in January 1925, Capone's car was shot up without him in it. Twelve days later, on January 24, Torrio was returning from a shopping trip with his wife Anna, when he was shot several times by North Side gunmen. After recovering, he effectively resigned and handed control to Capone, age 26 at the time. Torrio retired to New York and acted as an advisor to the New York Mafia in helping form the "Commission".{{Cite book|last=Lindberg|first=Richard|title=Gangland Chicago: Criminality and Lawlessness in the Windy City|publisher=Rowman & Littlefield|year=2016|isbn=9781442231955|location=Lanham, Maryland|pages=246}}

During the beer wars, the Capone gang's enforcement group was led by "Machine Gun" Jack McGurn, and included Tony Capezio, Claude "Screwy" Maddox, Sam "Golf Bag" Hunt, Frank Rio, and others. 1925–1926 were the most violent years of Chicago's "Beer Wars" in which 133 gangsters were murdered. On September 20, 1926, the North Side gang attacked Capone's headquarters at Cicero's Hawthorne Hotel, shooting hundreds of rounds and only narrowly missing Capone. Less than a month later, on October 11, North Side gang leader Hymie Weiss was gunned down with a Thompson in front of Holy Name Cathedral, allegedly by Jack McGurn. Weiss was succeeded by Vincent Drucci, a WW1 veteran and close friend of Weiss.

In 1928, the Capone gang was active in the violent Pineapple Primary election. Capone had previously donated $200,000 to Big Bill Thompson's corrupt mayoral campaign, and then used his gangsters to intimidate, assault, and bomb Thompson's political rivals in an attempt to keep the Republican party in power.

Capone was widely assumed to have been responsible for ordering the 1929 Saint Valentine's Day Massacre in an attempt to eliminate Bugs Moran, head of the North Side Gang. On that fateful and cold February morning, four Capone henchmen (two dressed as Chicago policemen) entered the S.M.C Cartage Company garage located at 2122 N. Clark St. Chicago, Illinois, to find seven men, which included five of Moran's soldiers, an auto mechanic, and a friend of the gangsters, awaiting a shipment of hijacked booze. All seven men were lined up against the wall in a mock police raid and shot to death. Moran escaped narrowly by accidentally arriving late to the meeting. Moran was the last survivor of the North Side gunmen; his succession had come about because his similarly aggressive predecessors Vincent Drucci and Hymie Weiss had been killed in the violence that followed the murder of original leader Dean O'Banion.{{cite book

| title = The Five Families

| date = May 13, 2014

| publisher = MacMillan

| url=https://books.google.com/books?id=5nAt6N8iQnYC

| page={{page needed|date=June 2014}} | isbn = 9781429907989

}}{{Cite web|url=http://www.bugsmoran.net/|archive-url=https://web.archive.org/web/20150903184250/http://www.bugsmoran.net/northsiders/drucci.html|url-status=usurped|title=George 'Bugs' Moran|archive-date=September 3, 2015|website=Bugs Moran}}[http://www.myalcaponemuseum.com/id111.htm My Al Capone Museum] [http://www.myalcaponemuseum.com/id111.htm "Vincent 'The Schemer' Drucci"], Mario Gomes, accessed 2/7/14

Capone was convicted on three counts of income tax evasion on October 17, 1931,{{cite web|url=https://www.britannica.com/biography/Al-Capone|title=Al Capone - American criminal|website=Encyclopedia Britannica|date=July 2, 2023 }}{{cite news |url=https://www.newspapers.com/clip/14736139/capone_convicted/ |newspaper=Chicago Sunday Tribune |last=Kinsley |first=Philip |title=U.S. jury convicts Capone |date=October 19, 1931 |page=1}}{{cite news|url=https://news.google.com/newspapers?id=kRpWAAAAIBAJ&pg=6214%2C983876 |newspaper=Spokesman-Review |location=(Spokane, Washington) |agency=Associated Press |title=Capone convicted of tax evasion |date=October 18, 1931 |page=1}} and was sentenced a week later to 11 years in federal prison, fined $50,000 plus $7,692 for court costs, and was held liable for $215,000 plus interest due on his back taxes.{{cite news |url=https://news.google.com/newspapers?id=kTdWAAAAIBAJ&pg=5020%2C6914884|newspaper=Eugene Register-Guard |location=(Oregon) |agency=Associated Press |last=Hackler |first=Victor |title=Capone sentenced 11 years, fined $50,000 |date=October 24, 1931 |page=1}}{{cite news |url=https://www.newspapers.com/clip/14342512/1931_10_24_capone_sentenced_front_page/ |newspaper=Chicago Sunday Tribune |title=Capone in jail; prison next |date=October 25, 1931 |page=1}}{{cite news|url=https://news.google.com/newspapers?id=f5kRAAAAIBAJ&pg=2892%2C4301 |newspaper=Eugene Register-Guard |location=(Oregon) |agency=Associated Press |last=Brennan |first=Ray |title=Capone kept until Monday for appeal |date=October 25, 1931 |page=1}}{{cite web|title=Visitors to the Court-Historic Trials |publisher=US District Court-Northern District of Illinois |access-date=2011-02-10 |url=http://www.ilnd.uscourts.gov/home/CourtHouseVisitors.aspx |url-status=dead |archive-url=https://web.archive.org/web/20110721065913/http://www.ilnd.uscourts.gov/home/CourtHouseVisitors.aspx |archive-date=2011-07-21}} Capone later died of heart failure as a result of apoplexy on January 25, 1947.{{cite news |url=https://www.newspapers.com/clip/14735502/al_capone_dies/ |work=Chicago Sunday Tribune |agency=Associated Press |title=Al Capone dies in Florida villa |date=January 26, 1947 |page=1}}{{cite news|url=https://www.nytimes.com/learning/general/onthisday/bday/0117.html |title=Capone Dead At 48. Dry Era Gang Chief|agency=Associated Press |work=The New York Times |date=2009-04-02 |access-date=2010-03-12| quote= Al Capone, ex-Chicago gangster and prohibition era crime leader, died in his home here tonight. |archive-url=https://web.archive.org/web/20100128035701/http://www.nytimes.com/learning/general/onthisday/bday/0117.html| archive-date= 28 January 2010 | url-status=live}}

In 1931, head of operations Frank Nitti was also convicted of tax evasion and sent to prison; however, Nitti received an 18-month sentence.Eghigian, Mars. After Capone: The Life and World of Chicago Mob Boss Frank "The Enforcer" Nitti. Naperville, Ill.: Cumberland House Publishing, 2006. {{ISBN|1-58182-454-8}} When Nitti was released on March 25, 1932, he took his place as the new boss of the Capone Gang. However, some historical revisionists claim that the real power in the Outfit was his underboss, Paul Ricca. Not only did Ricca frequently overrule Nitti's orders, but the leaders of the National Crime Syndicate dealt solely with him. Ricca would be the crime boss of Chicago, either in name or in fact, for the next 40 years.{{cite book |title=The Mafia Encyclopedia |url=https://archive.org/details/mafiaencyclopedi00sifa |url-access=registration |last=Sifakis |first=Carl |year=1987 |publisher=Facts on File |location=New York City |isbn=0-8160-1856-1 }}

Over the next decade, The Outfit moved into labor racketeering, gambling, and loan sharking. Geographically, this was the period when Outfit muscle extended to Milwaukee and Madison, Wisconsin, Kansas City, and especially to Hollywood and other California cities, where The Outfit's extortion of labor unions gave it leverage over the motion picture industry.

In the early 1940s, a handful of top Outfit leaders went to prison because they were found to be extorting Hollywood by controlling the unions that compose Hollywood's movie industry, and manipulating and misusing the Teamsters Central States Pension fund.{{cite book|last=Binder|first=John|title=The Chicago Outfit|year=2003|publisher=Arcadia Publishing|isbn=0738523267|page=56}}

In 1943, the Outfit was caught red-handed shaking down the Hollywood movie industry. Ricca wanted Nitti to take the fall. However, Nitti had found that he was claustrophobic, years earlier while in jail for 18 months (for tax evasion), and he decided to end his life rather than face more imprisonment for extorting Hollywood. Ricca then became the boss in name as well as in fact, with enforcement chief Tony Accardo as underboss—the start of a partnership that lasted for almost 30 years. Around this time, the Outfit began bringing in members of the Forty-Two Gang, a notoriously violent youth gang. Among them were Sam "Momo" Giancana, Sam "Mad Sam" DeStefano, Felix "Milwaukee Phil" Alderisio, and Fiore "Fifi" Buccieri.

Ricca was sent to prison later in 1943 for his part in The Outfit plot to control Hollywood. He was sentenced to 10 years in prison, along with a number of other mobsters. Through the "magic" of political connections, the whole group of Outfit mobsters was released after three years, largely due to the efforts of Outfit "fixer" Murray "The Camel" Humphreys. Ricca could not associate with mobsters as a condition of his parole. Accardo nominally took power as boss, but actually shared power with Ricca, who continued behind the scenes as a senior consultant—one of the few instances of shared power in organized crime.

Accardo joined Ricca in semi-retirement in 1957 due to some "heat" that he was getting from the IRS. From then on, Ricca and Accardo allowed several others to nominally serve as boss, such as Giancana, Alderisio, Joey Aiuppa, William "Willie Potatoes" Daddano, and Jackie "the Lackey" Cerone. Most of the front bosses originated from the Forty-Two Gang. However, no major business transactions took place without Ricca and Accardo's knowledge and approval, and certainly no "hits". By staying behind the scenes, Ricca and Accardo lasted far longer than Capone. Ricca died in 1972, leaving Accardo as the sole power behind the scenes.

File:1963 Chicago Outfit chart.png chart of the Chicago Outfit hierarchy in 1963]]

File:Joseph Aiuppa, 1979, Chicago Boss Mafia.png]]

During the 1960 presidential election, many claimed that the Mafia, and in particular, the Chicago Outfit, boosted candidate and future president John F. Kennedy. The strategy for boosting votes for Kennedy essentially ran through the Mafia-controlled unions, physically threatening those who did not vote for Kennedy. It was even said that Joseph Kennedy held a meeting with mob boss Sam Giancana before the election.{{Cite web |date=2020-10-22 |title=Did the Chicago Outfit elect John F. Kennedy president? |url=https://themobmuseum.org/blog/did-the-chicago-outfit-elect-john-f-kennedy-president/ |access-date=2022-04-01 |website=The Mob Museum |language=en-US}} Supposedly, the Kennedys and the Mafia agreed that if John were elected president, he would lighten the pursuit of authorities on the mob group. However, after the election, President Kennedy turned on Giancana. Theories say this is what led to his and Robert Kennedy's assassinations. Further, many believe the Outfit was involved in a Central Intelligence Agency–Mafia collusion during Castro's overthrow of the Cuban government. In exchange for its help, the Outfit was to be given access to its former casinos if it helped overthrow Fidel Castro in Operation Mongoose or Operation Family Jewels.{{cite web |url=https://www.theguardian.com/world/2007/jun/27/usa.cuba |title=CIA conspired with the mafia to kill Castro |last=Tisdall |first=Simon |author-link=Simon Tisdall |work=The Guardian |date=June 26, 2007 |access-date=May 24, 2013}} The Outfit failed in that endeavor and faced increasing indictments under the administration of President John F. Kennedy.

The Outfit reached the height of its power in the early 1960s. Accardo used the Teamsters pension fund, with the aid of Meyer Lansky, Sidney Korshak, and Jimmy Hoffa, to engage in massive money laundering through the Outfit's casinos. The Outfit controlled casinos in Las Vegas and "skimmed" millions of dollars over the course of several decades. Most recently, top mob figures have been found guilty of crimes dating back to as early as the mid-1960s. It has been rumored that the $2 million skimmed from the casinos in the Court case of 1986 was used to build the Old Neighborhood Italian American Club, the founder of which was Angelo J. "The Hook" LaPietra. The 1995 Martin Scorsese movie Casino depicts The Outfit's activities in Las Vegas during the 1970s, where bookmaker Frank "Lefty" Rosenthal and made man Anthony "The Ant" Spilotro managed the Stardust, Fremont, Marina, and Hacienda casinos on behalf of Joey "Doves" Aiuppa.{{cite book |author=Pileggi, Nicholas |title=Casino: Love and Honor in Las Vegas |isbn=0-684-80832-3 |date=1995 |publisher=Simon & Schuster|url-access=registration |url=https://archive.org/details/casinolovehonori00pile|access-date=September 5, 2019|archive-url=https://web.archive.org/web/20130820061350/https://archive.org/details/casinolovehonori00pile|archive-date=August 20, 2013|url-status=live}}

The 1970s and 1980s were a hard time for the Outfit, as law enforcement continued to penetrate the organization, spurred by poll-watching politicians. Off-track betting reduced bookmaking profits, and illicit casinos withered under competition from legitimate casinos. Activities such as auto theft and professional sports betting did not replace the lost profits. In the 1970s and early 1980s, a series of over 20 murders resulted from the Outfit's takeover of car theft rackets on the South Side of Chicago and Northwest Indiana.[https://www.newspapers.com/article/chicago-tribune-sam-annerino-murdered/134484284/ Stolen car racket spurs mob warfare] John O'Brien, Chicago Tribune (July 27, 1977) {{Webarchive|url=https://web.archive.org/web/20240524205207/https://www.newspapers.com/article/chicago-tribune-sam-annerino-murdered/134484284/ |date=May 24, 2024 }}[https://www.nytimes.com/1977/07/31/archives/new-chicago-experiences-a-surge-in-gang-slayings-former-policeman.html 'New' Chicago Experiences a Surge in Gang Slayings] Douglas E. Kneeland, The New York Times (July 31, 1977) {{Webarchive|url=https://web.archive.org/web/20240523233922/https://www.nytimes.com/1977/07/31/archives/new-chicago-experiences-a-surge-in-gang-slayings-former-policeman.html |date=May 23, 2024 }}[https://www.newspapers.com/article/the-times-19831211-chop-shops-dauber-cat/55694889/?locale=en-GB Car theft wars: the victim] Timothy Bannon, The Times of Northwest Indiana (December 11, 1983) {{Webarchive|url=https://web.archive.org/web/20240524205430/https://www.newspapers.com/article/the-times-19831211-chop-shops-dauber-cat/55694889/?locale=en-GB |date=May 24, 2024 }}[https://gangsterreport.com/the-chop-shop-wars-mafia-in-chicago-assumed-control-of-car-theft-industry-in-bloody-fashion/ The Chop Shop Wars: Mafia In Chicago Assumed Control Of Car-Theft Industry In Brutal Fashion] Scott Burnstein, GangsterReport.com (September 26, 2016) {{Webarchive|url=https://web.archive.org/web/20210414195635/https://gangsterreport.com/the-chop-shop-wars-mafia-in-chicago-assumed-control-of-car-theft-industry-in-bloody-fashion/ |date=April 14, 2021 }} During this period, known as the "chop shop wars", James "Jimmy the Bomber" Cataura, the head of the Chicago Heights crew, was tasked by Outfit leaders with seizing control of auto theft operations from a vast network of independent car thieves in the Chicago area. Cataura himself was a victim of the "chop shop wars" when he was killed in July 1978 amidst a power struggle within his own crew with underling Albert Tocco for control of the lucrative stolen car rings. The Outfit simultaneously waged a campaign to gain control over independent pornographic bookstores, massage parlors and strip clubs in and around Chicago, with several gangland-style murders being attributed to the "porn wars".[https://www.chicagotribune.com/1988/07/01/mob-grave-now-linked-to-porn-war/ Mob Grave Now Linked to Porn War] Chicago Tribune (July 1, 1988) {{Webarchive|url=https://web.archive.org/web/20240204130744/https://www.chicagotribune.com/1988/07/01/mob-grave-now-linked-to-porn-war/ |date=February 4, 2024 }}

Beginning in 1977, the Outfit engaged in a "loose alliance" with the Outlaws Motorcycle Club to control and share the profits from organized prostitution in Chicago.[https://www.newspapers.com/article/herald-and-review/61657820/ Outlaws called "criminal"] Herald & Review (March 2, 1983) {{Webarchive|url=https://web.archive.org/web/20230831002502/https://www.newspapers.com/article/herald-and-review/61657820/ |date=August 31, 2023 }}

Allen Dorfman, a key figure in the Outfit's money embezzlement operations, was investigated by the Department of Justice. In 1982, the FBI wire-tapped Dorfman's personal and company phone lines and was able to gather the evidence needed to convict Dorfman and several of his associates on attempts to bribe a state senator to get rid of the trucking industry rates. If Dorfman had succeeded, the Outfit would have seen a huge gain of profit. This was known as Operation Pendorf and was a huge blow to the Chicago crime syndicate.{{Cite news|url=https://www.chicagotribune.com/1997/03/31/retiring-fbi-agent-recalls-bugging-role-in-teamsters-case/|title=Retiring FBI Agent Recalls Bugging Role in Teamsters Case|work=tribunedigital-chicagotribune|access-date=2017-04-16|language=en}}

Operation GAMBAT (GAMBling ATtorney) proved to be a crippling blow to the Outfit's tight grip on the Chicago political machine. Pat Marcy, a made man in the Outfit, ran the city's First Ward, which represented most of downtown Chicago. Marcy and company controlled the circuit courts from the 1950s until the late 1980s with the help of Alderman Fred Roti and Democratic Committeeman John D'Arco Sr. Together, the First Ward fixed cases involving everything from minor traffic violations to murder.

Attorney and First Ward associate Robert Cooley was one of the lawyers who represented many mafiosi and associates in which cases were fixed. As a trusted man within the First Ward, Cooley was asked to "take out" a city police officer. Cooley was also an addicted gambler and in debt, so he approached the U.S. Justice Department's Organized Crime Strike Force, declaring that he wanted to "destroy Marcy and the First Ward".

Cooley was soon in touch with the FBI and began cooperating as a federal informant. Through the years, he maintained close ties to Marcy and the big shots of the First Ward. He wore an electronic surveillance device, recording valuable conversations at the notorious "First Ward Table", located at "Counselor's Row" across the street from Chicago City Hall. The results in Operation Gambat (Gambling Attorney) were convictions of 24 corrupt judges, lawyers, and cops.

In February 1990, 20 members and associates of the Outfit's "Ferriola Street Crew", which was headed by Joseph Ferriola before being taken over by Ernest Rocco Infelice upon Ferriola's death, were indicted on various federal charges including murder, extortion and bribery following an eight-year FBI investigation.[https://www.chicagotribune.com/1990/02/08/20-linked-to-mob-indicted/ 20 Linked to Mob Indicted] Chicago Tribune (February 8, 1990) {{Webarchive|url=https://web.archive.org/web/20240525012732/https://www.chicagotribune.com/1990/02/08/20-linked-to-mob-indicted/ |date=May 25, 2024 }}[https://www.latimes.com/archives/la-xpm-1990-02-08-mn-489-story.html 20 Chicagoans Accused of Being Top Mobsters Indicted] Larry Green, Los Angeles Times (February 8, 1990) {{Webarchive|url=https://web.archive.org/web/20230429100709/https://www.latimes.com/archives/la-xpm-1990-02-08-mn-489-story.html |date=April 29, 2023 }}

Accardo died in 1992.{{cite news|last=Baumann|first=Edward|title=Former FBI Agent Bill Roemer Takes a Look at Mob Boss Tony Accardo|url=https://www.chicagotribune.com/1995/10/29/former-fbi-agent-bill-roemer-takes-a-look-at-mob-boss-tony-accardo/|newspaper=Chicago Tribune|date=October 29, 1995|access-date=March 2, 2015}} In a measure of how successfully he had managed to stay out of the limelight, he never spent a day in jail (or only spent one day, depending on the source) despite an arrest record dating to 1922. Chicago's transition from Accardo to the next generation of Outfit bosses has been more of an administrative change than a power struggle, distinct from the way that organized crime leadership transitions take place in New York City.

Higher law enforcement investigations and general attrition led to the Outfit's gradual decline since the late 20th century.[https://abc7chicago.com/chicago-outfit-today-al-capone-death/11508957/ 75 years to the day after Al Capone's death, it's not your father's Chicago Outfit] Chuck Goudie, Barb Markoff, Christine Tressel and Ross Weidner, ABC 7 (January 26, 2022) {{Webarchive|url=https://web.archive.org/web/20230314204808/https://abc7chicago.com/chicago-outfit-today-al-capone-death/11508957/ |date=March 14, 2023 }}[https://torontosun.com/news/world/gangland-usa-philly-mob-and-chicago-outfit-are-on-the-abyss Gangland USA: Philly mob and Chicago Outfit are on the abyss] Brad Hunter, Toronto Sun (February 5, 2023) {{Webarchive|url=https://web.archive.org/web/20230315093630/https://torontosun.com/news/world/gangland-usa-philly-mob-and-chicago-outfit-are-on-the-abyss |date=March 15, 2023 }} The Old Neighborhood Italian American Club is considered to be the hangout of old timers as they live out their golden years.{{citation needed|date=July 2015}} The club's founder was Angelo J. LaPietra "The Hook", who was the main Council at the time of his death in 1999.

On April 25, 2005, the U.S. Department of Justice launched Operation Family Secrets,[https://docs.google.com/gview?a=v&q=cache:0hazFO3699QJ:www.usdoj.gov/usao/iln/pr/chicago/2005/pr0425_01.pdf+operation+family+secrets&hl=en&gl=us] {{dead link|date=March 2015}} which indicted 14 Outfit members and associates under the Racketeer Influenced and Corrupt Organizations Act (RICO), including Joseph Lombardo, Nicholas Calabrese, Frank Calabrese Sr. and James Marcello. U.S. District Court Judge James Zagel presided over the Family Secrets trial. The federal prosecutors were Mitchell A. Mars, T. Markus Funk, and John Scully. Facing a life sentence, Nicholas Calabrese became the first "made" member of the Chicago Outfit to become a witness for the federal government. Calabrese gave information on 14 murders he was personally involved with and knowledge of 22 killings during the past 30 years.

As of 2007, the Outfit's size is estimated to be 28 official members (composing its core group) and more than 100 associates.{{cite web|url=http://abclocal.go.com/wls/story?section=news/local&id=5681103|title=ABC7 WLS : Chicago and Chicago News|publisher=Abclocal.go.com|access-date=January 29, 2015|archive-url=https://web.archive.org/web/20131216034853/http://abclocal.go.com/wls/story?section=news%2Flocal&id=5681103|archive-date=December 16, 2013|url-status=dead}}

From 1996 to 2018, the Chicago Outfit was believed to be led by John DiFronzo.{{cite web |title=Who's Who in Chicago Outfit for 1997 ISPN-97-10-12 |url=http://www.ipsn.org/cc97.html |url-status=dead |archive-url=https://web.archive.org/web/20170521220053/http://www.ipsn.org/cc97.html |archive-date=May 21, 2017 |access-date=December 4, 2011 |publisher=Ipsn.org}} As of 2021, the Chicago Outfit is believed to be led by Salvatore "Solly D" DeLaurentis.{{cite web |date=June 2018 |title=With top Chicago mob boss dead, Outfit looks for new blood-06-1-18 |url=https://abc7chicago.com/john-no-nose-difronzo-chicago-mob-outfit-boss/3550181/ |access-date=January 8, 2021 |publisher=abc7chicago.com}} On May 31, 2020, 24 year-old Bobby 'Boo Boo' English Jr. was murdered. The Cicero crew-affiliated 12th Street Players gang is suspected of ordering the hit. He was the son of Bobby "Taz" English, former boss of the 12th Street Players during the 1990s and early 2000s and currently in prison for attempted murder.{{Cite web |last=Burnstein |first=Scott |date=2024-05-30 |title=More Questions Than Answers Four Years Later: Was Killing Of Bobby “Boo Boo” English, Jr. The Last Chicago Mob Hit? - The Gangster Report |url=https://gangsterreport.com/more-questions-than-answers-four-years-later-was-killing-of-bobby-boo-boo-english-jr-the-last-chicago-mob-hit/ |access-date=2025-02-11 |website=gangsterreport.com |language=en-US}}

• 1910–1920: Vincenzo "Big Jim" Colosimo – murdered on May 11, 1920.
• 1920–1925: John "Papa Johnny" Torrio – retired in 1925 after an assassination attempt.
• 1925–1931: Alphonse "Al" Capone – imprisoned in 1931.
• 1931–1943: Frank "The Enforcer" Nitti – committed suicide on March 19, 1943.
• 1943–1947: Paul "The Waiter" Ricca – imprisoned in 1943; stepped down in 1947.
• 1947–1957: Anthony "Big Tuna" Accardo – stepped down in 1957, becoming a "shadow executive" of the Outfit.{{cite web |url=https://www.angelfire.com/americangangland/lacosanostra/outfit/main.html |title=American Gangland: The Chicago Outfit |date=February 10, 2014 |publisher=Angelfire.com|access-date=March 2, 2015}}
• 1957–1966: Salvatore "Sam" Giancana – fled to Mexico to avoid imprisonment in 1966; deposed by Ricca and Accardo.
• 1966–1967: Salvatore "Sam" Battaglia – imprisoned in 1967.
• 1967–1971: Felix "Milwaukee Phil" Alderisio – imprisoned 1967–1969; died September 25, 1971.
• 1971–1986: Joseph "Joey Doves" Aiuppa – imprisoned in 1986.
• 1986–1996: Samuel "Sam Wings" Carlisi – imprisoned in 1996; died on January 2, 1997.
• 1997–2001: John "Johnny Apes" Monteleone – former capo of 26th Street/Chinatown crew before becoming boss;{{cite news |last1=JOSEPH FOSCO |title=Mafia Report: Chicago Outfit – Addendum Three |url=https://www.americannewspost.com/josephfosco/8910/mafia-report-chicago-outfit-addendum-three-3/ |access-date=31 December 2023 |agency=New Paper |publisher=American News Post |date=24 June 2020}} died in January 2001.{{cite news |last1=Cam Simpson and Matthew Walberg |title=Mob boss gunned down in Lyons |url=https://www.chicagotribune.com/news/ct-xpm-2001-11-22-0111220047-story.html |access-date=31 December 2023 |agency=New Paper |publisher=Chicago Tribune |date=22 November 2001}}
• 2001–2006: James "Little Jimmy" Marcello – imprisoned for life in 2009.
• 2006–2010: Michael "Fat Mike" Sarno – imprisoned in 2012.
• 2010–2018: John "No Nose" DiFronzo – died on May 27, 2018.
• 2018–present: Salvatore "Solly D" Delaurentis

The street boss is a high-ranking member appointed to run the outfit's daily activities for the boss. The position was created to protect the boss from federal investigations.

• 1986–1989: Joseph "Joe Nagall" Ferriola – deceased from heart troubles in 1989.
• 1989–1993: John "No Nose" DiFronzo – sentenced for racketeering in 1993–1994
• 1993–1994: Joseph "Joe the Builder" Andriacchi – stepped down
• 1994–1997: John "No Nose" DiFronzo – stepped down
• 2001–2003: Alfonso "Al the Pizza Man" Tornabene – stepped down
• 2012–2016: Louis "Louie Tomatoes" Marino – stepped down, died March 7, 2017
• 2016–present: Albert "Albie the Falcon" Vena

• 1910–1920: John "Papa Johnny" Torrio – became boss in 1920.
• 1920–1925: Alphonse "Scarface Al" Capone – became boss in 1925.
• 1925–1931: Frank "The Enforcer" Nitti – became boss in 1931.
• 1931–1943: Louis "Little New York" Campagna – arrested in 1943, deceased in 1955.
• 1943–1947: Tony "Joe Batters" Accardo – became boss in 1947.
• 1947–1957: Salvatore "Mooney Sam" Giancana – became boss in 1957, murdered in 1975.
• 1957–1964: Frank "Strongy" Ferraro – died in 1964.
• 1964–1966: Samuel "Teets" Battaglia – became boss in 1966, deceased in 1973.
• 1967–1986: John "Jackie the Lackey" Cerone – imprisoned in 1986, deceased in 1996.
• 1986–1992: John "No Nose" DiFronzo – also served as Street boss.
• 1992–1996: James "Jimmy the Man" Marcello – imprisoned.
• 1996–2006: Anthony "Little Tony" Zizzo – disappeared and probably murdered in 2006.
• 2006–2009: Joseph "Joe the Builder" Andriacchi – retired briefly due to illness.
• 2009–2020: Salvatore "Sammy Cards" Cataudella – became acting underboss
• 2020–2023: James "Jimmy I" Inendino – died on February 23, 2023.{{Cite news |last=Burnstein |first=Scott |date=February 24, 2023 |title=Dotting The I From The Heavens: Chicago Outfit Heavyweight Jimmy Inendino Dead At 80, Left Legacy Of Love & Fear |work=The Gangster Report |url=https://gangsterreport.com/dotting-the-i-from-the-heavens-chicago-outfit-heavyweight-jimmy-inendino-dead-at-83-left-legacy-of-love-fear/ |archive-url=https://web.archive.org/web/20230225122603/https://gangsterreport.com/dotting-the-i-from-the-heavens-chicago-outfit-heavyweight-jimmy-inendino-dead-at-83-left-legacy-of-love-fear/ |archive-date=February 25, 2023}}{{Cite news |date=February 23, 2023 |title=James "Jimmy I." Inendino - Obituary |work=Russo's Hillside Chapels |url=https://www.russohillsidechapels.com/obituary/JamesJimmyI-Inendino |access-date=February 25, 2023}}
• Acting 2020–2023: Salvatore "Sammy Cards" Cataudella – became official underboss
• 2023–present: Salvatore "Sammy Cards" Cataudella

• 1925–1928: Antonio "Tony the Scourge" Lombardo – murdered in 1928.
• 1928–1947: Charles "Trigger Happy" Fischetti – retired in 1947, deceased in 1951.
• 1947–1957: Paul "The Waiter" Ricca – retired in 1957, deceased in 1972.
• 1957–1992: Tony "Joe Batters" Accardo – deceased from natural causes in 1992.
• 1992–1999: Angelo J. LaPietra – deceased from natural causes in 1999.
• 1999–2007: Joseph "Joey the Clown" Lombardo – sentenced in 2007 and imprisoned in 2009; died on October 19, 2019, at the age of 90.{{cite web |title=Notorious Chicago mobster Joey 'The Clown' Lombardo dead at age 90 |url=https://www.fox32chicago.com/news/notorious-chicago-mobster-joey-the-clown-lombardo-dead-at-age-90 |website=FOX 32 Chicago |date=October 20, 2019 |access-date=21 October 2019}}{{cite web |title=Chicago Mobster Joey 'The Clown' Lombardo Dies While Serving Life Sentence |url=https://chicago.cbslocal.com/2019/10/20/reputed-mobster-joey-the-clown-lombardo-dies-while-serving-life-sentence/ |website=CBS Chicago |date=October 20, 2019 |access-date=21 October 2019}}
• 2007–2009: Alfonso "Al the Pizza Man" Tornabene – deceased in 2009.
• 2009–2020: Marco "The Mover" D'Amico – semi active by 2016, allowing Andriacchi to assist DeLaurentis, died from natural causes 2020.
• Acting 2012–2016: Joseph "Joe the Builder" Andriacchi
• 2020–2024: Joseph "Joe the Builder" Andriacchi — deceased in 2024
• Acting 2022–present: John A. Matassa

• Boss – Salvatore "Solly D" DeLaurentis{{cite web|url=http://gangsterreport.com/chicago-mob-state-union-still-flying-15/|title=Chicago Mob State of The Union – Still Flying in 2015 – The Gangster Report|website=gangsterreport.com|date=January 25, 2015|access-date=2016-09-15}} – born in 1939. Inducted in either 1988 or 1989 and put in charge of Lake County, Illinois. He was indicted in 1993 along with Ernest "Rocky" Infelice, Louis "Louie Tomatoes" Marino, Robert "Bobby The Gabeet" Bellavia, Harry Aleman, Marco "The Mover" D'Amico, and several others, in the Good Ship Lollipop Case, which centered on mob murders by the Cicero Street Crew and sent to prison for 17 years.[https://www.chicagotribune.com/1995/02/08/us-trying-reputed-mob-figure-again/ U.S. Trying Reputed Mob Figure Again] Chicago Tribune (February 8, 1995) {{Webarchive|url=https://web.archive.org/web/20240425212403/https://www.chicagotribune.com/1995/02/08/us-trying-reputed-mob-figure-again/ |date=April 25, 2024 }}[https://www.chicagotribune.com/1993/08/25/lake-county-mobster-gets-18-12-year-term/ Lake County Mobster Gets 18 1/2-Year Term] Chicago Tribune (August 25, 1993) {{Webarchive|url=https://web.archive.org/web/20240425213115/https://www.chicagotribune.com/1993/08/25/lake-county-mobster-gets-18-12-year-term/ |date=April 25, 2024 }} He was released in 2006.{{cite web |title=With top Chicago mob boss dead, Outfit looks for new blood |url=https://abc7chicago.com/with-top-chicago-mob-boss-dead-outfit-looks-for-new-blood/3550181/ |website=ABC Chicago |date=June 2018 |access-date=16 October 2019}} His role in the Outfit between 2007 and 2014 when he became boss is unclear, though it is theorized that he was a co-capo of the Cicero Crew.
• Street Boss – Albert "Albie the Falcon" Vena{{cite web|url=http://gangsterreport.com/gr-sources-chicago-outfits-falcon-flies-to-street-boss-post-vena-riding-high-sans-handcuffs-for-now-at-least/|title=GR Sources: Chicago Outfit's 'Falcon' Flies To Street Boss Post, Vena Riding High Sans Handcuffs (For Now, At Least) |website=gangsterreport.com|date=August 14, 2016|access-date=2016-09-15}} – born in 1948. Part of the new administration following the retirement of John DiFronzo. Vena was once a powerful capo of the Grand Avenue crew and replaced Joseph Lombardo after his 2007, conviction of a 1974 murder.{{cite web |title=Reputed Mobster Plotted Heist To Have A Happy Holiday, Feds Say |url=https://chicago.cbslocal.com/2016/12/23/reputed-mobster-plotted-heist-to-have-a-happy-holiday-feds-say/ |website=CBS Chicago |date=December 23, 2016 |access-date=16 October 2019}} By 2000, Vena had been acquitted of 2 murders.{{cite web |last1=Jackson |first1=David |title=Oct. 24, 2000: 3 unsolved slayings link police, mob crews |url=https://www.chicagotribune.com/news/ct-xpm-2000-10-24-0010240114-story.html |website=Chicago Tribune |date=October 24, 2000 |access-date=6 July 2022}} FBI investigators from the August 2006, disappearance case of Anthony Zizzo considered him a suspect.{{cite web |title=FBI seeks info 10 years after Chicago mob boss Anthony Zizzo vanished |url=https://abc7chicago.com/news/fbi-seeks-info-10-years-after-chicago-mob-boss-vanished/1493318/ |website=ABC Chicago |date=September 2016 |access-date=16 October 2019}} In 1993, Vena was acquitted of the November 4, 1992 murder of Samuel Taglia who was shot twice in the head and had his throat cut with a knife, his body dumped in the trunk of his 1983 Buick car. His most trusted confidants were reported to be Joseph Andriacchi and James Inendino.
• Underboss – Salvatore "Sammy Cards" Cataudella – former acting underboss; convicted of racketeering related to a prostitution scheme in 1990.{{Cite web |title=United States of America, Plaintiff-appellee, v. Vito Caliendo, Susan Barker, Salvatore Cataudella and Thomasstathas, Defendants-appellants, 910 F.2d 429 (7th Cir. 1990) |url=https://law.justia.com/cases/federal/appellate-courts/F2/910/429/463461/ |access-date=2021-04-17 |website=Justia Law |language=en}}
• Consigliere – Vacant
• Acting Consigliere – John "Pudgy" Matassa Jr. – currently acting consigliere. Matassa took over the North Side/Rush Street Crew.{{cite web |last1=UNITED STATES DISTRICT COURT NORTHERN DISTRICT OF ILLINOIS EASTERN DIVISION |title=UNITED STATES OF AMERICA, and LABORERS' INTERNATIONAL UNION OF NORTH AMERICA by and through ROBERT LUSKIN, in his official capacity as General Executive Board Attorney, Plaintiffs, V. CONSTRUCTION & GENERAL LABORERS' DISTRICT COUNCIL OF CHICAGO AND VICINITY, an affiliated entity of the Laborers' International Union of North America, Defendant. |url=http://laborers_chicago.tripod.com/complaintnew.htm |publisher=Laborers for JUSTICE |access-date=9 July 2023}}{{cite web |title=I-Team Report: The Mob's Babysitter |url=https://abc7news.com/archive/6752224/ |website=ABC News |access-date=7 July 2022}} In 2019, Matassa pleaded guilty in a scheme aimed at fraudulently qualifying for early retirement benefits.{{cite news |last1=Goudie |first1=Chuck |author2= Christine Tressel |title=As underworld workforce ages, John "Pudgy" Matassa claims he's sickly in move for sentencing delay |url=https://abc7chicago.com/john-pudgy-matassa-chicago-outfit-heart-problems-sentencing-delay/5291513/ |access-date=9 July 2023 |agency=News |publisher=ABC7 Chicago |date=10 May 2019}}

• Frank "Toots" Caruso – Capo of the 26th Street/Chinatown Crew.
• Rudolph "Rudy" Fratto – Capo of the Elmwood Park Crew; Peter DiFronzo was the captain before his death in December 2020.{{cite news|url=http://chicago.suntimes.com/crime/2020/12/6/22156468/peter-difronzo-brother-john-difronzo-chicago-outfit-boss-dies-coronavirus |title=Peter DiFronzo, brother of Chicago Outfit boss, dies from coronavirus |newspaper=Chicago Sun Times |date=December 6, 2020}} Rudy Fratto became Caporegime by 2021. Fratto was born in 1943. He was first identified as a member of the Chicago Outfit in 1997. In October 2009, he pleaded guilty to tax evasion.{{cite web |title=Another Chicago Mobster Goes Down for Tax Evasion |url=https://www.nbcchicago.com/news/local/another-chicago-mobster-goes-down/1863959/ |website=NBC Chicago |date=October 14, 2009 |access-date=7 July 2022}}{{cite web |title=Web Exclusive: Mob's Rudy no role model |url=https://abc7news.com/archive/7064224/ |website=ABC News |access-date=7 July 2022}} In September 2012, he was sentenced to 1-year imprisonment for bid-rigging $2 million in forklift contracts for a pair of trade shows at McCormick Place.{{cite web |last1=Goudie |first1=Chuck |title=Chicago mobster stiffs feds on restitution, suggests he's being gouged |url=https://abc7chicago.com/rudy-fratto-chicago-outfit-restitution-i-team/1981759/ |website=ABC Chicago News |access-date=7 July 2022}} Theories have arisen that he and Michael "Mags" Magnafichi have been running the crew jointly as co-capos, though sources dispute this as Magnafichi has reportedly not been active in years.
• Nicholas "Jumbo" Guzzino - Chicago Heights Crew. According to Nick Calabrese he became a made man in 1983, and was sponsored by Dominick Palermo, a powerful underboss in the Chicago Heights Crew under Albert Tocco. Took over whatever remained of the old Chicago Heights Crew. It is possible and highly likely that he is retired.
• Louis "Louie" Rainone – Capo of the Cicero Crew.{{cite news |last1=Burnstein |first1=Scott M. |title=The Golden Touch In Cicero: New Power Player, Louie Rainone, Emerges In Chicago Mob Circles, Per Sources |url=https://gangsterreport.com/the-golden-touch-in-cicero-new-power-player-louie-rainone-emerges-in-chicago-mob-circles-per-sources/ |access-date=9 July 2023 |agency=News |publisher=Gangster Report |date=2023}} In 2012, Rainone's business the Roosevelt Gold Exchange was robbed by five suspects.{{cite news |title=Five men wanted in jewelry store beating, robbery |url=https://abc7chicago.com/archive/8765519/ |access-date=9 July 2023 |agency=News |publisher=ABC7 Chicago |date=7 August 2012}}
• Christopher "Christy the Nose" Spina – Capo of the Grand Ave Crew. Spina was a long time member of the Grand Avenue Crew and a close associate of Albert Vena. He was also the driver of Joey Lombardo and at one time he worked for Chicago's Bureau of Signs and Markings.{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-1999-07-27-9907270176-story.html|title=The Nose Shows Almost Anything Goes Under Daley Watch|first=John|last=Kass|website=chicagotribune.com|date=July 27, 1999 }} In 1993, Spina lost his foreman job at the First Ward sanitation yard when the City of Chicago stated he was chauffeuring Joseph Lombardo around.{{cite news |last1=Rhodes |first1=Steve |title=The Lost Don: When FBI agents showed up last spring to arrest the Chicago mob boss Joey "The Clown" Lombardo, there was a problem: he wasn't there, and he hadn't been seen since. But Lombardo is more than a vanishing act. He's one of a vanishing breed—a last link to the Chicago Outfit's blood-spattered heyday. |url=https://www.chicagomag.com/chicago-magazine/october-2005/the-lost-don/ |access-date=9 July 2023 |agency=News |publisher=Chicago magazine |date=3 October 2005}}

• Robert Bellavia: former member of the Ferriola crew.{{cite web |title=United States v. Salerno |url=https://caselaw.findlaw.com/us-7th-circuit/1316784.html |website=FindLaw |access-date=16 October 2019}} He was involved in the February 7, 1985 murder of bookmaker Hal C. Smith, the body was recovered 3 days later in the trunk of his car.{{cite web |title=United States v. Marino, 835 F. Supp. 1501 (N.D. Ill. 1993) |url=https://law.justia.com/cases/federal/district-courts/FSupp/835/1501/1984045/ |website=Justia US Law |access-date=16 October 2019}}{{cite web |title=ChicagoOutfit|url=https://yourcostuminfo.blogspot.com |website=yourcostuminfo.blogspot.com}}{{cite web |title=Sucker's Bets: Murder & Intrigue on the Good Ship Lollipop |url=http://www.ipsn.org/lolli1.html |website=IPSN |access-date=16 October 2019 |archive-date=April 24, 2019 |archive-url=https://web.archive.org/web/20190424063020/http://www.ipsn.org/lolli1.html |url-status=dead }} In 1990, he was indicted and later convicted in the Good Ship Lollipop case, a large-scale racketeering and murder indictment alongside Ernest Infelice, Solly DeLaurentis, Harry Aleman, James Nicholas and William DiDomenico.{{cite web |title=Judge refuses to release reputed mobsters afraid of AIDS |url=https://www.upi.com/Archives/1991/08/13/Judge-refuses-to-release-reputed-mobsters-afraid-of-AIDS/4445682056000/ |website=UPI |access-date=16 October 2019}} He was released in 2016 after serving 25 years in prison.
• Paul "Paulie" Carparelli: Cicero crew, debt collector and high-ranking member of Twelfth Street Players gang.{{Cite web |last=Meisner |first=Jason |date=February 3, 2016 |title=Reputed mob debt collector's recordings read like low-grade gangster script |url=https://www.chicagotribune.com/news/ct-chicago-outfit-violence-threats-met-20160203-story.html |website=chicagotribune.com}}
• Michael Carioscia: born 1933. In December 1950, he was arrested on charges of armed robbery and was sentenced to 2 years' imprisonment, he was released in 1954. He was sentenced to 5 years imprisonment in October 1961 on narcotics charges after he and Armando Pennacchio made three sales of a large quantity of heroin to an undercover FBN officer.{{cite book |title=Traffic in Opium and Other Dangerous Drugs |year=1962 |publisher=United States Bureau of Narcotics |page=43 |url=https://books.google.com/books?id=PcFIAQAAIAAJ&q=michael+1961+chicago+narcotics&pg=PA43 |access-date=17 October 2019}}{{cite book |title=Organized Crime and Illicit Traffic in Narcotics: Hearings Before ..., Parts 1-5 |date=1964 |publisher=By United States. Congress. Senate. Committee |page=1103 |url=https://books.google.com/books?id=0uREAQAAMAAJ&q=michael+Carioscia+mafia+chicago&pg=PA1103 |access-date=17 October 2019}} He has a brother named Frank.
• Frank Caruso Jr.: son of 26th Street crew Capo Frank "Toots" Caruso was arrested for beating a black boy in 1998.{{Cite web |title=Verdict in Chicago Beating Case |url=https://apnews.com/article/61f411164b66816db45faca6cd69bc11 |website=Associated Press}}
• Dominick "Mennie" Cassano: Elmwood Park soldier and brother of Gino "Mean Gene" Cassano and Angelo "The Angel" Cassano (deceased). He and his brothers were convicted of attempted murder in 1993.
• Gino "Mean Gene" Cassano: Elmwood Park soldier and brother of Dominick "Mennie" Cassano and Angelo "The Angel" Cassano (deceased). He and his brothers were convicted of attempted murder in 1993.{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-1993-06-30-9306300218-story.html|title=2 In Urso Beating Convicted of Battery|first=Jon|last=Hilkevitch|website=chicagotribune.com|date=June 30, 1993 }}
• Anthony "Tony" Dote: In November 1994, he was indicted on charges of racketeering and illegal gambling. He pleaded guilty to the charges in 1996 and was sentenced to 4 years imprisonment.{{cite web |last1=O'Connor |first1=Matt |title=7 Men Accused of Running Chicago-Area Sports Bookmaking Business |url=https://www.chicagotribune.com/news/ct-xpm-2000-04-29-0004290214-story.html |website=Chicago Tribune |date=April 29, 2000 |access-date=6 July 2022}}{{cite web |title=United States v. Dote |url=https://caselaw.findlaw.com/us-7th-circuit/1136912.html |website=FindLaw |access-date=6 July 2022}}
• Nicholas "Nick" Ferriola: born in 1977. He is the son of Joseph Ferriola. He was sentenced by U.S. District Judge James Zagel in 2008 to 3 years in federal prison for his role in the Family Secrets case, he was accused of extortion and illegal sports gambling charges over an 8-year period, Ferriola admitted to earning over $150,000 per month.{{cite web|title=Ferriola gets 3 years |url=http://blogs.suntimes.com/mob/2008/09/ferriola_gets_3_years.html |work=Chicago Sun-Times |access-date=February 2, 2013 |url-status=dead |archive-url=https://web.archive.org/web/20121012100141/http://blogs.suntimes.com/mob/2008/09/ferriola_gets_3_years.html |archive-date=October 12, 2012 |df=dmy }} He served as a trusted confidant to Frank Calabrese Sr. during the operation including after Calabrese's life imprisonment sentence in 2009.
• Gary "Gags" Gagliano: Gagliano is the nephew of Joseph Gagliano, a close associate of Jackie Cerone. He is a member of the Elmwood Park Crew.[https://casetext.com/case/united-states-v-frontier-1 United States v. Frontier] Casetext (March 22, 2023) {{Webarchive|url=https://web.archive.org/web/20230514094522/https://casetext.com/case/united-states-v-frontier-1 |date=May 14, 2023 }}
• Michael "Jaws" Giorango: former associate of the Chicago Heights crew.{{cite web |title=Jaws takes a bite |url=https://illinoistimes.com/article-2905-jaws-takes-a-bite.html |website=Illinois Times |publisher=Rich Miller |access-date=16 October 2019 |archive-date=October 16, 2019 |archive-url=https://web.archive.org/web/20191016041928/https://illinoistimes.com/article-2905-jaws-takes-a-bite.html |url-status=dead }} He pleaded guilty to operating a bookmaking ring in the suburbs of South Chicago in 1989 and used threats of violence to collect unpaid debts including threats of beatings, bombings and robbery. In 1990, he was sentenced to prison and served 4 years. In 2010, reports linked him and Alexi Giannoulias, the 72nd Democratic Illinois treasurer, to a $11–20 million loan.{{cite web |title=Convicted felon Giorango faces losing old town apartment building |url=https://www.chicagobusiness.com/article/20130812/CRED03/130819988/convicted-felon-giorango-faces-losing-old-town-apartment-building |website=Chicago Business |date=August 11, 2013 |access-date=16 October 2019}}{{cite web |title=Giannoulias' Family Bank Loaned Money to Felons: Report |url=https://www.nbcchicago.com/blogs/ward-room/Giannoulias-Family-Bank-Loaned-Money-to-Felons-Report-89765182.html |website=NBC Chicago |access-date=16 October 2019 |archive-date=October 16, 2019 |archive-url=https://web.archive.org/web/20191016041937/https://www.nbcchicago.com/blogs/ward-room/Giannoulias-Family-Bank-Loaned-Money-to-Felons-Report-89765182.html |url-status=dead }}{{cite book |title=The Case Against Barack Obama: The Unlikely Rise and Unexamined Agenda of the Media's Favorite Candidate |date=August 4, 2008 |publisher=David Freddoso |page=29 |isbn=9781596985773 |url=https://books.google.com/books?id=g9dHcCTE2zgC&q=michael+giorango+1990&pg=PA228 |access-date=16 October 2019}} In 2004, he was sentenced to six months of intermittent confinement and three years of probation for prostitution charges in Miami. He was granted early release from probation in 2008. In 2010, he filed for bankruptcy protection and listed assets and liabilities between $500,000 and $1 million.{{cite web |title=Amid loan dispute, Giorango seeks sanctuary in bankruptcy |url=https://www.chicagobusiness.com/article/20130521/CRED03/130529947/amid-loan-dispute-giorango-seeks-sanctuary-in-bankruptcy |website=Chicago Business |date=May 20, 2013 |publisher=Abraham Tekippe |access-date=16 October 2019}} His case was dismissed in 2013.
• Dino Marino: Son of Louis "Louie Tomatoes" Marino and driver of Solly D. He was arrested for a no-show job as Health Department inspector for the Town of Cicero.{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-2000-04-20-0004200232-story.html|title=Prison Term in Cicero Ghost-Payroll Case|first=Matt|last=O'Connor|website=chicagotribune.com|date=April 20, 2000 }}
• John "Pudgy" Matassa: former captain and former secretary-treasurer of the Independent Union of Amalgamated Workers Local 711 and outfit soldier.{{Cite web|url=https://www.chicagotribune.com/news/breaking/ct-met-reputed-mob-figure-guilty-20190226-story.html|title=Reputed mob figure John Matassa Jr. pleads guilty to embezzlement scheme|first=Jason|last=Meisner|website=chicagotribune.com|date=February 26, 2019 }}
• Robert “Bobby Pinocchio” Panozzo: Panozzo is a former member of the C-Notes street gang and soldier of the Grand Avenue crew. He was sentenced to 18 years on state racketeering charges on January 8, 2019.
• Joseph Jerome "Jerry" Scalise: Outfit soldier, best known for stealing the Marlborough diamond. Currently incarcerated.{{Cite web|url=https://abc7chicago.com/6826473/|title=Chicago mob's 'Marlborough Man' Jerry Scalise wants out of sentence early|first1=Chuck|last1=Goudie|first2=Barb|last2=Markoff|first3=Christine|last3=Tressel|first4=Ross|last4=Weidner|date=October 7, 2020|website=ABC7 Chicago}}
• Michael "A1 Mike" Zitello: Cicero soldier and bookmaker. He is a former protege of Louis "Louie Tomatoes" Marino.{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-1993-03-02-9303186590-story.html|title=Mob Gambling Figure Sentenced|website=chicagotribune.com|date=March 2, 1993 }}

• Dominic Buttitta: Outfit soldier, Strip Club owner and father of fellow mobster Anthony Buttitta. They both were arrested by the FBI for an illegal internet gambling business.{{Cite web |title=Father and Son Operators of Elgin Adult Entertainment Club and Internet Gambling Business Sentenced to Prison Terms for Concealing More Than $4.6 Million of Income from the IRS |url=https://www.fbi.gov/chicago/press-releases/2012/father-and-son-operators-of-elgin-adult-entertainment-club-and-internet-gambling-business-sentenced-to-prison-terms-for-concealing-more-than-4.6-million-of-income-from-the-irs |website=FBI}}
• Anthony Buttitta: Outfit soldier and son of fellow mobster Dominic Buttitta. They both were arrested by the FBI for an illegal internet gambling business.{{Cite web |title=Feds Eye Who's Who in Sandoval Case |url=https://www.pressreader.com/usa/chicago-tribune-sunday/20191013/281505047979261 |website=PressReader}}
• Michael "Mickey" Davis: Close associate of Salvatore DeLaurentis. In June 2015, he was found guilty of extortion and was sentenced to 4 years imprisonment.{{cite web |title=United States of America v. Michael Mickey Davis |url=https://caselaw.findlaw.com/us-7th-circuit/1763564.html |access-date=7 July 2022 |website=FindLaw}}
• Carlo "The Fat Man/Carl D" Dote: Elmwood Park soldier, cafe owner and bookmaker.{{Cite web |title=Village Gives Convicted Mob Bookmaker Job With Public Works |url=https://www.pressreader.com/usa/chicago-sun-times/20131202/281582353425314 |website=PressReader}}
• Gioacchino "Jack" Galione: Elmwood Park associate he and Gene "Mean Gene" Cassano were on trial for assaulting Luigi Mucerino over a $10,000 juice loan.{{cite web | url=https://www.casino.org/news/sweepstakes-operators-extortion-trial-sinks-when-organized-crime-mentioned/ | title=Sweepstakes Operator's Extortion Trial Sinks when 'Organized Crime' Mentioned | date=March 12, 2024 }} The charges were later dismissed.{{cite web | url=https://uk.news.yahoo.com/charges-dropped-federal-juice-loan-174200000.html?guccounter=1&guce_referrer=aHR0cHM6Ly93d3cuZ29vZ2xlLmNvbS8&guce_referrer_sig=AQAAAH8Ky_yhKc-HMmaZnUOFpcZ1hjK4cw4Vsg4bXJkYak0i2Bz6fIu9ILMCPCixU5mKdgOlP5ysozTGywWzgt3ASFccjMvvkK2tRpA3yMnVUfq2wnUC5YYsLVX5E_yIrJ5FkkleKFpEW3857IsVEEZebHwZjkekEmQTuM-47QZeU2re | title=Charges dropped in federal juice loan extortion case that had roots in Chicago mob probe | date=March 25, 2024 }}
• Paul Koroluk: joint leader of the P-K street crew. The crew is named after the leaders Robert Panozzo Sr. and Koroluk. The P-K crew posed as police officers to rob drug houses on Chicago's South and West Sides.{{Cite web |last=Burnstein |first=Scott |date=August 31, 2015 |title=GR Exclusive: Feds Eager To Get Chicago's Team Hollingshead To Turn On Vena, Assert Sources |url=https://gangsterreport.com/gr-exclusive-feds-eager-to-get-team-hollingshead-to-turn-on-vena/}} Koroluk is currently serving an 18-year prison sentence on RICO charges.{{cite web |title=Illinois Department of Corrections - Inmate Search |url=https://www.idoc.state.il.us/subsections/search/ISinms2.asp?idoc=B69547}}
• Rocco "Rocky" Lombardo: Lombardo is the brother of Joseph Lombardo, former Chicago Outfit Consigliere. In 2007, he was sentenced to 5 years probation for tax fraud.{{cite web |last1=Gibson |first1=Ray |date=February 22, 2007 |title=Lombardo brother gets probation in tax fraud |url=https://www.chicagotribune.com/news/ct-xpm-2007-02-22-0702220157-story.html |access-date=6 July 2022 |website=Chicago Tribune}}{{cite book |last1=Jay |first1=Timothy |url=https://books.google.com/books?id=rx6ZDQAAQBAJ&dq=rocco+lombardo+chicago&pg=PA211 |title=We Did What?! Offensive and Inappropriate Behavior in American History |date=2016 |publisher=Abc-Clio |isbn=9781440837739 |page=211 |access-date=6 July 2022}}
• Frank Orlando: At his trial, the FBI alleged Orlando introduced printing firm owner Mark Dziuban to Paul Carparelli to discuss extortion attempts.{{cite web |date=February 16, 2015 |title=Jury convicts Carol Stream executive in extortion case |url=https://www.dailyherald.com/article/20150216/news/150219106/ |archive-url=https://web.archive.org/web/20150218210309/http://www.dailyherald.com/article/20150216/news/150219106 |url-status=dead |archive-date=February 18, 2015 |access-date=16 October 2019 |website=Daily Herald}} In 2014, he was sentenced to almost 4 years in prison on extortion charges.{{cite web |date=April 7, 2015 |title=Suburban dad gets 4 years for acting as middleman in extortion racket |url=https://chicago.suntimes.com/2015/4/7/18430168/suburban-dad-gets-4-years-for-acting-as-middleman-in-extortion-racket |access-date=16 October 2019 |website=Chicago Sun Times}}
• Rick Rizzolo: Strip Club owner and Outfit soldier in Las Vegas.{{Cite web |date=October 27, 2017 |title=Former Las Vegas strip club mogul sent back to prison |url=https://www.reviewjournal.com/crime/courts/former-las-vegas-strip-club-mogul-sent-back-to-prison/}}
• Filippo "Gigi" Rovito: Burr Ridge restaurant owner{{cite web |date=December 3, 2021 |title=Burr Ridge Mishandled Restaurant's Liquor License: Ex-Official |url=https://patch.com/illinois/burrridge/burr-ridge-mishandled-restaurants-liquor-license-ex-official}} was sentenced to 6 years imprisonment for kidnapping and rape in 1997.{{cite web |title=FindLaw's Appellate Court of Illinois case and opinions |url=https://caselaw.findlaw.com/il-court-of-appeals/1064158.html}} He was hired by Mickey Davis to arrange the beating of R.J. Serpico the owner of Ideal Motors, a used-car dealership in Melrose Park. R.J. Serpico had a $300,000 debt by Salvatore DeLaurentis. The beating never happens because one of the men who Gigi has hired, George Brown was an FBI informant.{{cite web |date=November 17, 2015 |title=Pal of Outfit boss gets 4 years for extortion |url=https://chicago.suntimes.com/2015/11/17/18461489/pal-of-outfit-boss-gets-4-years-for-extortion}}
• Emil "Nick The Badge" Schullo: Former Cicero Police chief. He was convicted in 2002 in a federal racketeering case alongside Chicago Mafioso Michael (Big Mike) Spano and then-Cicero Mayor Betty Loren-Maltese. He awarded a contract to a security company owned by Spano.{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-2003-01-03-0301030239-story.html|title=2 get prison sentence in Cicero kickbacks|first=Matt O'Connor, Tribune staff|last=reporter|website=chicagotribune.com|date=January 3, 2003 }}
• Anthony Volpendesto: Volpendesto was convicted along with Michael Sarno and Outlaws member Mark Polchan in 2014 for running the illegal gambling establishment "C&S Amusements" in Cicero.{{cite web | url=https://law.justia.com/cases/federal/appellate-courts/ca7/11-3022/11-3022-2014-03-24.html | title=USA v. Anthony Volpendesto, No. 11-3022 (7th Cir. 2014) }} His father was the mobster Sam Volpendesto.[https://abc7.com/archive/7790619/ Feds start trial against Outfit, bike gang members] ABC 7 (November 16, 2010)

• Joseph "Joe the Builder" Andriacchi – former consigliere.{{Cite news |last=Burnstein |first=Scott |date=January 7, 2023 |title=The State Of The Mob In Chicago: Winds Of Change Blowing In Windy City "Outfit," Solly D, Jimmy I Preparing For Syndicate's Future |work=The Gangster Report |url=https://gangsterreport.com/the-state-of-the-mob-in-chicago-winds-of-change-blowing-in-windy-city-outfit-solly-d-jimmy-i-preparing-for-syndicates-future/ |archive-url=https://web.archive.org/web/20230108141943/https://gangsterreport.com/the-state-of-the-mob-in-chicago-winds-of-change-blowing-in-windy-city-outfit-solly-d-jimmy-i-preparing-for-syndicates-future/ |archive-date=January 8, 2023}} Andriacchi was a cousin by marriage to Joey "The Clown" Lombardo, Andriacchi was charged with the disappearance of Anthony Zizzo in 2006. He died in August 2024.{{cite web |title=Chicago mob boss Joe 'The Sledgehammer' Andriacchi dies at 91, sources tell I-Team |url=https://abc7chicago.com/post/old-time-chicago-mob-boss-joe-sledgehammer-andriacchi-dies-91-sources-team/15183289/ |access-date=14 August 2024 |website=ABC News}}
• James "Jimmy Poker" DiForti – former loanshark and secretary-treasurer of International Laborers Union Local 5 in Chicago Heights. In July 1997, DiForti was charged with the 1988 murder of William Benham. DiForti died on June 6, 2000.[https://www.chicagotribune.com/2000/06/24/james-diforti-55-ex-official-of-labor-union/ James DiForti, 55, Ex-Official of Labor Union] Chicago Tribune (June 24, 2000) {{Webarchive|url=https://web.archive.org/web/20240404044310/https://www.chicagotribune.com/2000/06/24/james-diforti-55-ex-official-of-labor-union/ |date=April 4, 2024 }}
• James "Jimmy I" Inendino – former underboss and capo of the Cicero Crew. According to sources, Inendino operated as captain of the Cicero crew since 2010.{{cite web |title=Meeting with a mob enforcer |url=https://abc7chicago.com/archive/5956633/ |access-date=7 July 2022 |website=ABC News}} He died on February 23, 2023.

The Outfit is notable for having had other ethnic groups besides Italians as high-ranking associates since the family's earliest days. A prime example of this was Jake "Greasy Thumb" Guzik, a Polish Jew, who was the top "bagman" and "accountant" for decades until his death. Others were Murray Humphreys, who was of Welsh descent, Gus Alex, a Greek, and Ken Eto (aka Tokyo Joe), who was Japanese-American.

Another well-known associate of the Outfit is Jewish New York City mobster Benjamin Siegel. Siegel was a childhood friend of Capone.{{sfn|Tereba|2012|pp=24–25}} Siegel's organization in Las Vegas and Los Angeles was an ally of the Outfit from 1933 to 1961 when the family boss, Mickey Cohen, was imprisoned and the family was decimated.

• Louis Bombacino – born in 1923. He was a former bookmaker.{{cite news |title=Organized Crime Spreads To Fast-Growing Arizona |url=https://www.nytimes.com/1976/06/14/archives/organized-crime-spreads-to-fastgrowing-arizona.html |website=The New York Times |date=June 14, 1976 |access-date=18 October 2019}} Between 1965 and 1967, Bombacino contacted the FBI while in prison awaiting trial on a robbery charge.{{cite journal |title=452 F. 2d 274 - United States v. Cerone |url=https://openjurist.org/452/f2d/274/united-states-v-cerone |website=Open Jurist |volume=F2d |issue=452 |page=274 |access-date=18 October 2019|last1=Circuit |first1=Seventh }} He admitted to involvement in a large-scale bookmaking operation under the control of Jackie Cerone and Fiore Buccieri.{{cite book |title=C-1 and the Chicago Mob |date=2014 |publisher=Vincent L. Inserra |page=179 |isbn=9781493182794 |url=https://books.google.com/books?id=sj2tBAAAQBAJ&q=Louis+Bombacino+1967&pg=PA179 |access-date=18 October 2019}} He was murdered in Tempe, Arizona on the morning of October 6/7, 1975 by the Chicago Outfit while hiding under the alias "Joe Nardi", Paul Schiro and Tony Amadio were suspected in the car bombing.{{cite news |title=Car Blast Kills Witness |url=https://www.nytimes.com/1975/10/08/archives/car-blast-kills-witness.html |website=The New York Times |date=October 8, 1975 |access-date=18 October 2019}}{{cite web |title=Tagging of explosives: hearings before the Subcommittee on Criminal Laws and Procedures of the Committee on the Judiciary, United States Senate, Ninety-fifth Congress, first session [-second session on S. 2013 ...., Part 1 |url=https://books.google.com/books?id=YDLQAAAAMAAJ&q=1975+october+Louis+Bombacino&pg=PA17 |website=Google books |year = 1978|publisher=United States. Congress. Senate. Committee |access-date=18 October 2019}}{{cite web |title=40 years later: Who murdered reporter Don Bolles? |url=http://www.tucsonsentinel.com/local/report/060216_bolles_murdered/40-years-later-who-murdered-reporter-don-bolles/ |website=Tucson Sentinel |publisher=Jon Talton |access-date=18 October 2019}} His testimony against Cerone resulted in 5 years' imprisonment in May 1970 and he relocated to Arizona and secured a warehouse job before his murder.{{cite book |title=The Mafia: A Guide to an American Subculture: A Guide to an American Subculture |date=2013 |publisher=Nate Hendley |page=44 |isbn=9781440803611 |url=https://books.google.com/books?id=RRWMAQAAQBAJ&q=jackie+cerone+may+1970&pg=PA44 |access-date=18 October 2019}}
• George Brown – associate (2016): Brown worked as a debt under Paul Carparelli. After he became an FBI informant he testified against Mickey Davis and Paul Carparelli, that he was hired to break both legs of the Melrose Park car dealer R.J. Serpico. His testimonial helped to arrest outfit members and associates: Robert McManus, Michael "Mickey" Davis, Mark Dziuban, Frank Orlando, Vito Iozzo, James Amabile and Paul Carparelli.{{cite web | url=https://chicago.suntimes.com/2016/4/8/18365980/mob-debt-collector-s-cooperation-pays-off-with-light-sentence | title=Mob debt collector's cooperation pays off with light sentence | date=April 8, 2016 |access-date=March 5, 2024}}{{cite web | url=https://www.chicagotribune.com/news/ct-chicago-outfit-violence-threats-met-20160203-story.html | title=Reputed mob debt collector's recordings read like low-grade gangster script | website=Chicago Tribune | date=February 3, 2016 }}
• Richard Cain – born in October 1931. He served as Chief Investigator for the Cook County Police Department. Cain joined the Chicago Police Department (Vice Squad) in 1956 until 1960.{{cite news |title=Lawman Who Joined Mobsters Is Gunned to Death in Chicago |url=https://www.nytimes.com/1973/12/22/archives/lawman-who-joined-mobsters-is-gunned-to-death-in-chicago.html |website=The New York Times |date=December 22, 1973 |access-date=18 October 2019}} In June 1961, Cain was allegedly met by a CIA staffer in Mexico City, he was deported from Mexico in 1962 for carrying a loaded gun and brass knuckles, violating his tourist permit by working and impersonating a Mexican government official.{{cite web |title=Salvatore Giancana and Richard Cain |url=https://www.archives.gov/files/research/jfk/releases/104-10133-10404.pdf |website=Gov Archives |access-date=18 October 2019}} He was released from prison in October 1971. On December 20, 1971, he was shot and killed on orders of the Chicago Outfit. Harry Aleman, Joey Lombardo and Frank Schweihs were suspected of killing him.
• Frank Calabrese Jr. – associate (2005)
• Nicholas Calabrese – born in November 1942. He is a former soldier in the Chicago Outfit. He was the brother of Frank Calabrese Sr. and uncle of Frank Calabrese Jr. and the star witness of the Family Secrets case. Calabrese was convicted for his involvement in 14 murders and sentenced to 12 years' imprisonment by District Judge James Zagel.
• Frank Cullotta – born in December 1938. He was a former associate and friend of Tony Spilotro, and was involved in his Hole in the Wall gang based in Las Vegas. In 1982, Cullotta was imprisoned and was approached by the FBI with a wiretap of Spilotro talking with someone about "having to clean our dirty laundry", which Cullotta took as an insinuated contract on his life.{{cite web|url=https://www.upi.com/Archives/1983/10/26/A-judge-refused-Wednesday-to-dismiss-murder-charges-against/8118435988800/|title=A judge refused Wednesday to dismiss murder charges against...|publisher=upi.com|date=October 26, 1983}} Due to this, in July 1982, Cullotta finalized an agreement with the prosecutors, sentenced to eight years in prison, but paroled in 1984 to the witness protection program.{{cite book|author1=Dennis N. Griffin|author2=Frank Cullotta|author3=Dennis Arnoldy|title=Cullotta: The Life of a Chicago Criminal, Las Vegas Mobster and Government Witness|year=2007|publisher=Huntington Press In|isbn=9780929712451|url=https://archive.org/details/isbn_9780929712451|url-access=registration|page=[https://archive.org/details/isbn_9780929712451/page/196 196]|quote=Bertha's Gifts and Jewelry robbery 1981.}} Cullotta died on August 20, 2020.{{cite newsgroup | author = John Przybys | title = Ex-mobster Frank Cullotta, crony of Tony Spilotro, dies in Las Vegas | date = August 20, 2020 | url = https://www.reviewjournal.com/local/local-las-vegas/ex-mobster-frank-cullotta-crony-of-tony-spilotro-dies-in-las-vegas-2100017/ | access-date = August 20, 2020 }}
• Ken Eto – born in 1919. He was a former Japanese-American Chicago Outfit associate.{{cite web |title=30 Years Later, Mob Hitmen Murders Remain Unsolved |url=https://chicago.cbslocal.com/2013/07/12/30-years-later-mob-hitmen-murders-remain-unsolved/ |website=CBS Chicago |date=July 12, 2013 |access-date=18 October 2019}} He arrived in Chicago from Washington in 1949. Eto's criminal record dates back to 1942 for violating a wartime curfew. In February 1983, Eto survived an assassination attempt on his life by Outfit hitmen Jasper Campise and John Gattuso after 3 bullets ricocheted off of his skull, he immediately joined protective custody and turned informant against the Outfit, Outfit captain Vincent Solano ordered the attempt. The assassination attempt is believed to have revolved around paranoia towards Eto following his guilty plea on illegal gambling charges, which provoked the Chicago Outfit to believe the possibility of Eto being easily persuaded to cooperate with the government against the Outfit. The hitmen, 68-year-old Jasper Campise and 47-year-old John Gattuso were offered government protection and declined, they were both found strangled and stabbed in July 1983 inside of the trunk of a 1981 Volvo registered to Campise.{{cite web |title=Two mob hitmen found killed and stuffed in car |url=https://www.upi.com/Archives/1983/07/16/Two-mob-hitmen-found-killed-and-stuffed-in-car/4971427176000/ |website=UPI |access-date=18 October 2019}} The FBI estimated his criminal earnings of between "$150,000 to $200,000" per week and bribe payoffs of $12,000 per month to Chicago policemen. He died in January 2004 at the age of 84 from natural causes.{{cite web |title=Tokyo Joe |url=https://abc7chicago.com/archive/6072155/ |website=ABC 7 |access-date=18 October 2019}}
• Jeff Hollingshead – associate (2014): Hollingshead was an associate of the Grand Avenue Crew and a member of the P-K street crew named after the leaders Robert Panozzo Sr. and Paul Koroluk. The P-K crew posed as police officers to rob drug houses on Chicago's south and west side.
• William "B.J." Jahoda – former associate. He operated a sports bookmaking ring with Sam Sammarco between 1976 and 1979. Jahoda later began a partnership with Rocco Infelise in 1979 through to 1988, the operation allegedly earned over $8 million in profits. He operated an illegal parlay card business with Michael Sarno, James Damopoulos, Salvatore DeLaurentis and Infelise from 1979 to 1983 in Lake County, Illinois and other parts of Chicago. He also operated the Rouse House casino in suburban Libertyville, Illinois in 1982 which generated approximately $500,000 in profits, during this time he paid Infelise $1500 monthly payments to bribe the Lake County Sheriff to get advance notice of law enforcement raids.{{cite web |title=The mob in the burbs |url=http://www.ipsn.org/news/mob_in_the_burbs.htm |website=Daily Herald |publisher=Robert McCoppin|access-date=20 October 2019 |archive-date=December 15, 2020 |archive-url=https://web.archive.org/web/20201215022638/http://www.ipsn.org/news/mob_in_the_burbs.htm |url-status=dead }}{{cite web |title=United States v. Marino, 835 F. Supp. 1501 (N.D. Ill. 1993) |url=https://law.justia.com/cases/federal/district-courts/FSupp/835/1501/1984045/ |website=Law Justia |access-date=19 October 2019}} By the fall of 1988, Infelise told Jahoda that he was paying $10,000 to the Cook County Police Department Sheriff for protection and that he used undersheriff and former Cook County Republican Party chairman James Dvorak as the intermediate, Dvorak was sentenced to 3½ years in prison in April 1994 for accepting bribes.{{cite web |title=Ex-con with past ties to Des Plaines no longer allowed in casinos |url=http://prev.dailyherald.com/story/?id=264668 |website=Daily Herald |publisher=Rob Olmstead |access-date=20 October 2019}}{{cite web |title=Illinois GOP Official Denies Claim He Received Bribes |url=https://www.latimes.com/archives/la-xpm-1990-02-15-mn-1200-story.html |website=Los Angeles Times |date=February 15, 1990 |access-date=20 October 2019}} In September 1989, Infelise confirmed that he was paying $35,000 altogether to incarcerated Outfit members and Chicago police officers.{{cite news |title=Illinois Republican Leaders Urge Cook County Chairman to Quit |url=https://www.washingtonpost.com/archive/politics/1990/02/18/illinois-republican-leaders-urge-cook-county-chairman-to-quit/a8140fd5-7657-4b21-846b-d7d199414d78/ |newspaper=The Washington Post |access-date=20 October 2019}}{{cite book |title=Corrupt Illinois: Patronage, Cronyism, and Criminality |date=December 19, 2014 |publisher=Dick Simpson |page=102 |isbn=9780252097034 |url=https://books.google.com/books?id=Ob3kBQAAQBAJ&q=james+dvorak+illinois+republican+party&pg=PA102 |access-date=20 October 2019}} In early 1990, the government alleged Infelise and Jahoda gave out a $50,000 loan to an undercover IRS agent under the identity of "Larry Weeks" who Infelise instructed to bribe a Wisconsin zoning official to gain favorable selection in their efforts to get commercial/industrial property near Lake Geneva, Wisconsin as residential property.{{cite web |title=20 Chicagoans Accused of Being Top Mobsters Indicted : Mafia: The charges include murder, extortion and bribery. The case is believed to be the first round in a massive probe of organized crime. |url=https://www.latimes.com/archives/la-xpm-1990-02-08-mn-489-story.html |website=Los Angeles Times |date=February 8, 1990 |access-date=20 October 2019}} He died in 2004.
• Leonard Patrick – born in October 1913. Former associate heavily involved in illegal gambling rackets active in the North Side of Chicago. In June 1933, he was sentenced to 10 years in prison for robbing a bank in Culver, Indiana. He came to the attention of the U.S. Attorney in 1958 as a Chicago Outfit affiliate. In 1975, Patrick was convicted of contempt after he refused to testify under immunity against Chicago police lieutenant Ronald O'Hara and admitted to payoffs of $500 per month to O'Hara.{{cite web |title=United States of America, Petitioner-appellee, v. Leonard Patrick, Respondent-appellant, 542 F.2d 381 (7th Cir. 1976) |url=https://law.justia.com/cases/federal/appellate-courts/F2/542/381/24890/ |website=Law Justia |access-date=19 October 2019}} Patrick was released in July 1978.{{cite web |title=xi. Leonard Patrick |url=https://www.aarclibrary.org/publib/jfk/hsca/reportvols/vol9/pdf/HSCA_Vol9_5Fxi_Patrick.pdf |website=aarc Library |publisher=Alderson Reporting Company Inc. |access-date=19 October 2019}} He pleaded guilty to criminal charges in April 1992. It is alleged the Outfit ordered the bombing of Sharon Patrick's car outside her home in Rogers Park, Chicago in May 1992, as a result of his guilty plea. In September 1992, he testified against the Chicago Outfit. He is believed to have been involved in, if not ordered, the 1965 assassination of 24th Ward Alderman Ben Lewis, the city's first black alderman and Democrat committeeman.{{cite web |title=The Murder Chicago Didn't Want to Solve |url=https://www.propublica.org/article/ben-lewis-murder |website=ProPublica |date=February 25, 2021 |access-date=2 March 2021}} He died in 2006.
• Gerald Scarpelli – soldier (1988)

The Chicago Outfit is composed of a number of factions, or "street crews", involved in various criminal activities, including loan sharking, gambling and labor racketeering. A percentage of the profits generated by these crews is paid to the organization's leaders.[https://www.fbi.gov/news/stories/the-chicago-mafia The Chicago Mafia: Down but Not Out] Federal Bureau of Investigation (June 27, 2011) {{Webarchive|url=https://archive.today/20170506062012/https://www.fbi.gov/news/stories/the-chicago-mafia |date=May 6, 2017 }} The Outfit's five original crews were based at Taylor Street, Grand Avenue, 26th Street, the North Side, and suburban Chicago Heights.[https://academic.oup.com/illinois-scholarship-online/book/18296/chapter-abstract/176319685?redirectedFrom=fulltext Street Crew Neighborhoods] Oxford University Press (December 2012) {{Webarchive|url=https://archive.today/20250523190003/https://academic.oup.com/illinois-scholarship-online/book/18296/chapter-abstract/176319685?redirectedFrom=fulltext |date=May 23, 2025 }} According to the FBI, four crews remain active as of 2025.[https://www.nbcchicago.com/investigations/is-the-mob-still-active-in-chicago-yes-but-its-not-what-you-might-expect/3746570/ Is the mob still active in Chicago? Yes, but it's not what you might expect] Chuck Goudie, Lisa Capitanini and Katy Smyser, NBC Chicago (May 15, 2025) {{Webarchive|url=https://archive.today/20250523185836/https://www.nbcchicago.com/investigations/is-the-mob-still-active-in-chicago-yes-but-its-not-what-you-might-expect/3746570/ |date=May 23, 2025 }}

• 26th Street Crew/Chinatown Crew/South Side Crew – The crew remains active.
• Chicago Heights Crew – The crew is defunct.
• Cicero Crew – The Cicero-based crew is the most influential in the Outfit.[https://gangsterreport.com/a-chicago-mob-summer-outfit-don-solly-d-cicero-crew-power-paulie-c-entourage-descend-on-taylor-st-for-italian-festival/ A Chicago Mob Summer: Outfit Don Solly D, Cicero Crew Power Paulie C & Entourage Descend On Taylor St. For Italian Festival] Scott Burnstein, The Gangster Report (August 16, 2024) The crew remains active.
• Elmwood Park Crew – The crew remains active.
• Grand Avenue Crew – The crew remains active.
• Melrose Park Crew/West Side Crew – The crew is defunct.
• North Side Crew/Rush Street Crew – Operating from Rush Street, the crew controlled rackets on Chicago's North Side and the adjoining suburbs.[https://ganglandwire.com/ken-eto-and-the-chicago-outfit/ Ken Eto and the Chicago Outfit] Gary Jenkins, Gangland Wire (January 18, 2022) {{Webarchive|url=https://archive.today/20250524184554/https://ganglandwire.com/ken-eto-and-the-chicago-outfit/ |date=May 24, 2025 }} The crew is defunct.
• Taylor Street Crew – The crew is defunct.

The Chicago Outfit has a long history of portrayal in Hollywood as the subject of film and television.{{Citation needed|date=September 2022}}

{{div col|colwidth=25em}}

• Little Caesar (1931)
• Scarface (1932)
• Chicago Syndicate (1955)
• The Scarface Mob (television film, 1959)
• Al Capone (1959)
• The St. Valentine's Day Massacre (1967)
• Point Blank (1967)
• Bullitt (1968)
• The Outfit (1973)
• Capone (1975)
• Thief (1981)
• Raw Deal (1986)
• The Untouchables (1987)
• Midnight Run (1988)
• Next of Kin (1989)
• The Firm (1993)
• Casino (1995)
• Payback (1999)
• Road to Perdition (2002)
• Public Enemies (2009)
• Chicago Overcoat (2009)
• Gangster Land (2017)
• Capone (2020)
• The Outfit (2022)

{{div col end}}

{{div col|colwidth=25em}}

• The Untouchables (1959–1963)
• The F.B.I. (1965–1974)
• Crime Story (1986–1988)
• The Untouchables (1993–1994)
• Sugartime (TV film) (1995)
• The Rat Pack (1998)
• Prison Break (2005–2009)
• The Chicago Code (2011)
• The Firm (2012)
• Mob Wives: Chicago (2012)
• The Mob Doctor (2012–2013)
• Boardwalk Empire (2010–2014)
• The Making of the Mob: Chicago (2016)

{{div col end}}

• 91 Days (since 2016)
• baccano! (2007)

• Scott, Sabrina Austen. The Lemon Tree Girl: A Mafia Story. Amazon, 2022. {{ISBN|979-8985541403}}

• Empire of Sin (2020)

• Joe Aiello – rival to Al Capone during Prohibition; was also allied to Salvatore Maranzano during the Castellammarese War{{cite web |author1=Thomas P. Hunt |author2=New Milford CT |url=http://www.onewal.com/w-aiello.html |title=The American Mafia – Joe Aiello |publisher=Onewal.com |date=October 23, 1930 |access-date=April 13, 2011 |url-status=dead |archive-url=https://web.archive.org/web/20101127170817/http://onewal.com/w-aiello.html |archive-date=November 27, 2010 |df=dmy-all }}
• Grand Rapids Hotel
• Hired Truck Program scandal
• North Side Gang – a rival gang to Al Capone
• Timeline of organized crime in Chicago
• Unione Siciliana

General:

• Crime in Chicago
• Italians in Chicago
• List of Italian Mafia crime families

{{Reflist}}

• {{cite book|author=Binder, John|title=The Chicago Outfit|publisher= Arcadia Publishing|date= 2003|isbn= 0-7385-2326-7}}
• {{cite book|author= Cooley, Robert|title=When Corruption Was King: How I Helped the Mob Rule Chicago, Then Brought the Outfit Down|date= 2004|publisher=Hachette Books |isbn=0-7867-1583-9}}
• Cooley, Will (2017). "Jim Crow Organized Crime: Black Chicago's Underground Economy in the Twentieth Century", in Building the Black Metropolis: African American Entrepreneurship in Chicago, Robert Weems and Jason Chambers, eds. Urbana: University of Illinois Press, 147–170. {{ISBN|978-0252082948}}.
• {{cite book|author=Lombardi, Mark|author-link=Mark Lombardi|author2=Richards, Robert Carleton|author3=Hobbs, Judith Richards|name-list-style=amp|title= Mark Lombardi: Global Networks|url=https://archive.org/details/marklombardiglob0000hobb|url-access=registration|publisher= Independent Curators|date= 2003|isbn=0-916365-67-0}} (Published for the traveling exhibition of Lombardi's work, Mark Lombardi Global Networks).
• {{cite book|author=Nolan, John Matthew|title=2,543 Days: A History of the Hotel at the Grand Rapids Dam on the Wabash River}}
• {{cite book|author=Russo, Gus|author-link=Gus Russo|title=The Outfit: The Role of Chicago's Underworld in the Shaping of Modern America|url=https://archive.org/details/outfitroleofchic00russ|url-access=registration|publisher= Bloomsbury USA|date= 2002|isbn= 1-58234-279-2}}
• {{Cite book|last=Tereba|first=Tere|author-link=Tere Tereba|url=https://www.worldcat.org/oclc/1016454937|title=Mickey Cohen : the life and crimes of L.A.'s notorious mobster|date=2012|publisher=ECW Press|isbn=978-1-4596-5049-7|location=Toronto, Ont.|oclc=1016454937}}

• {{cite web|url= http://www.thechicagosyndicate.com/ |website=thechicagosyndicate.com|title=The Chicago Syndicate }} (Mob news archive)
• {{cite web|url= https://www.fbi.gov/ |website=fbi.gov|title=The FBI}} (Historical archives)

{{Chicago Outfit}}

{{Murder, Incorporated}}

{{The Untouchables}}

{{American Mafia}}

{{Organized crime groups in the United States}}

{{Organized crime groups in Atlantic City}}

{{Organized crime groups in Chicago}}

{{Canadian gangs}}

{{authority control}}

Category:1910 establishments in Illinois

Category:Al Capone

Category:Gangs in Chicago

Category:Italian-American crime families

Category:Italian-American culture in Chicago

Category:Organizations established in 1910

Category:The Untouchables

Category:Underground organizations based in Chicago