Robert Shaw (Illinois politician)

Shaw and his identical twin brother, William, were born on July 31, 1937, in Fulton, Arkansas.{{cite web |last1=Joravsky |first1=Ben |title=Political veteran Robert Shaw sees no reason why he can't become mayor |url=https://www.chicagoreader.com/chicago/mayoral-election-robert-shaw-challenges-rahm-emanuel/Content?oid=14352211 |website=Chicago Reader |accessdate=November 18, 2020 |language=en |date=July 22, 2014}}{{cite web |title=The Honorable William E. Shaw's Biography |url=https://www.thehistorymakers.org/biography/honorable-william-e-shaw |website=The HistoryMakers |accessdate=November 18, 2020 |language=en}} His parents were sharecroppers.{{cite news |last1=Kass |first1=John |title=Ever the Fighter, Shaw Lives for the Spotlight and Small Victories |publisher=Chicago Tribune |language=en |date=July 29, 1990}}

• {{cite web |last1=Kass |first1=John |title=Ever the Fighter, Shaw Lives for the Spotlight and Small Victories |url=https://www.newspapers.com/image/389527197 |via=Newspapers.com |url-access=subscription |publisher=Chicago Tribune |page=C1 |access-date=21 March 2024 |language=en |date=July 29, 1990}}
• {{cite web |last1=Kass |first1=John |title=Shaw |url=https://www.newspapers.com/image/389528996 |via=Newspapers.com |url-access=subscription |publisher=Chicago Tribune |page=C5 |access-date=21 March 2024 |language=en |date=July 29, 1990}}

Shaw is black.{{cite web |last1=Powers |first1=Thomas |title=Marcin, Bertrand win races for council seats |url=https://www.newspapers.com/image/386932732 |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=April 4, 1979}} He grew up for a number of his early years in nearby Hope, Arkansas.{{cite web |last1=Turner |first1=Tatyana |title=Former 9th Ward Ald. Robert Shaw, a South Side Powerbroker, Dies at 83 |url=https://www.chicagotribune.com/news/breaking/ct-robert-shaw-obit-20210727-rilr5oiacnfgbdwgjxo7yc57ga-story.html |publisher=Chicago Tribune |access-date=August 9, 2021 |date=July 26, 2021}} In Hope, he was neighbours with future U.S. president Bill Clinton. He and his family next moved to St. Louis, Missouri. In 1952, Shaw's family relocated to Chicago, Illinois, settling on the city's West Side.

Shaw studied liberal arts at Kennedy–King College.

Shaw and his brother learned politics from working in the 24th Ward Regular Democratic organization run by Arthur X. Elrod on the city's west side.{{cite news |title=Robert Shaw |work=Chicago Sun-Times |date=February 6, 1998}} He got his start at seventeen by working for an assistant precinct captain in the 24th ward.{{cite web |last1=Belanger |first1=Christian |title=Enyia vs. Shaw vs. Emanuel |url=https://southsideweekly.com/enyia-vs-shaw-vs-emanuel/ |website=southsideweekly.com |publisher=South Side Weekly |accessdate=November 18, 2020 |date=May 7, 2014}} He later worked as a precinct captain for Benjamin F. Lewis, prior to Lewis' 1963 murder. He worked on Lewis' successful campaign for the Chicago City Council.

Shaw and his twin brother became involved in the African American civil rights movement. In 1969, Shaw moved to the South Side of Chicago, settling in the Roseland neighborhood. The Shaw brothers both moved to the far South Side of the city, believing it to be the best location to establish an African American-led Democratic Party organization. In the late-1970s, he moved to the city's 9th ward, on the South Side. From 1975 through 1978, Shaw was employed as an affirmative action and workers compensation executive at the Illinois Department of Labor.{{cite web |title=Democratic Candidates |url=https://www.newspapers.com/image/237218108 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 26, 2021 |language=en |url-access=subscription |date=December 29, 2009}}

Shaw served two tenures as the alderman from Chicago's ninth ward.{{cite web |last1=Keagle |first1=Lauri Harvey |title=Robert Shaw to seek assessor's seat |url=https://www.nwitimes.com/news/local/illinois/robert-shaw-to-seek-assessors-seat/article_c64c6755-4ed3-5687-a3f0-250e397d7cd1.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=August 18, 2009}}{{cite web |last1=Byrne |first1=John |title=Emanuel gets First Challenger: Old-School Pol Shaw |url=https://www.chicagotribune.com/politics/chi-emanuel-gets-first-challenger-oldschool-pol-shaw-20140313-story.html |website=chicagotribune.com |date=March 13, 2014 |publisher=Chicago Tribune |accessdate=November 18, 2020}} In 1975, Shaw ran his first campaign for the Chicago City Council, unsuccessfully challenging incumbent 9th ward alderman Alexander Adduci.

Shaw was elected to the Chicago City Council in 1979, this time defeating Adducci.{{Cite web |url=http://chsmedia.org/media/fa/fa/LIB/AldermansList.htm |title=Centennial List of Mayors, City Clerks, City Attorneys, City Treasurers, and Aldermen, elected by the people of the city of Chicago, from the incorporation of the city on March 4, 1837 to March 4, 1937, arranged in alphabetical order, showing the years during which each official held office. |access-date=December 24, 2018 |archive-url=https://web.archive.org/web/20180904052355/http://chsmedia.org/media/fa/fa/LIB/AldermansList.htm |archive-date=September 4, 2018 |url-status=dead }} Shaw used racially charged rhetoric during the campaign. Adducci filed a lawsuit accusing supporters of Shaw's campaign of forging a letter that made Adducci (who was white) appear racist. In 1979, the Illinois Board of Elections investigated allegations that Shaw had violated the state's Campaign Disclosure Act during his aldermanic campaign.{{cite web |last1=Unger |first1=Rudolph |last2=Alexrod |first2=David |title=Ald. Shaw doesn't show, calls probe 'a conspiracy' |url=https://www.newspapers.com/image/386797688 |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=December 1, 1979}}

Shaw rose to prominence as a main African American community ally of Mayor Jane Byrne. He received criticism from Black independents when he voted in favor of Byrne's redistricting map for the city's wards, which a federal court would subsequently rule as being unfair to African Americans and Latinos. When Black protesters showed up at the City Council chamber to protest Byrne's firing of Black members of the Chicago Board of Education and the Chicago Housing Authority Board, Shaw called for the removal of the protesters and stood in support of Byrne and Chicago Housing Authority chairman Charles Swibel. A January 1981 article by F. Richard Ciccone of the Chicago Tribune described Shaw as "no stranger to city council controversy, though only a freshman alderman".

In 1981, Shaw introduced legislation that would have stripped the city's personnel code by drastically increasing the number of patronage hires, taking 15,000 civil service jobs away from having job security and merit-based testing as a hiring practice. He partnered with Edward Vrdolyak on this legislation.{{cite web |last1=Kneeland |first1=Douglas E. |title=CHICAGO PATRONAGE BACKERS SEEK TO BLUNT CRITICISM (Published 1981) |url=https://www.nytimes.com/1981/01/17/us/chicago-patronage-backers-seek-to-blunt-criticism.html |website=The New York Times |accessdate=November 18, 2020 |date=January 17, 1981}} He would tell the media, "I asked my friends, Ed Vrdolyak and Fred Roti to help me out, and they did". Shaw also credited City Council floor leader Wilson Frost with assisting in redrafting the proposal on the City Council floor. The legislation was overwhelmingly approved in a city council vote. Shaw and Wilson Frost both argued that eliminating the personnel code, and its testing requirements, would be beneficial to Black job applicants. The legislation was ultimately vetoed by mayor Byrne, after facing strong opposition from Chicagoans (a Chicago Tribune poll found 76% of Chicagoans opposed removing the personnel code).{{cite web |last1=Ciccone |first1=F. Richard |title=Pol shows city patronage action opposed by voters |url=https://www.newspapers.com/image/386824268/ |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=January 18, 1981}}

In its obituary for Shaw, the Chicago Crusader credited him with supporting hundreds of ordinances in his two stints as an alderman that had the impact of providing more opportunities for black-owned businesses to do business with the city government.

In 1981, Shaw introduced legislation that would require gas stations to have public restrooms. This was quickly shot down by the City Council.{{cite web |last1=Brotman |first1=Barbara |title=ALDERMAN'S RESTROOM RESOLUTION UPHOLDS PUBLIC'S SACRED RIGHT TO |url=https://www.chicagotribune.com/news/ct-xpm-1987-10-01-8703140151-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=October 1, 1987}} In 1982, Shaw voted against the handgun ban ordinance championed by mayor Byrne. The legislation passed without his support.{{cite web |title=The Chicago Syndicate: Chicago Democrats and the Chicago Mob |url=https://www.thechicagosyndicate.com/2008/03/chicago-democrats-and-chicago-mob.html |website=www.thechicagosyndicate.com |publisher=The Chicago Syndicate |accessdate=November 19, 2020 |date=March 9, 2008}} In 1982, Shaw also introduced an ordinance that would have increased the salary of aldermen from $27,600 to $46,350.{{cite web |last1=Davis |first1=Robert |title=Big raises proposed for aldermen |url=https://www.newspapers.com/image/387727679 |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=July 16, 1982}} After this, Mayor Byrne publicly declared she would veto any pay raise for Chicago aldermen.{{cite web |last1=Davis |first1=Robert |title=Byrne warns she'd veto salary hike for aldermen |url=https://www.newspapers.com/image/387869210/ |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=July 21, 1982}}

Shaw lost reelection to Perry H. Hutchison in 1983.Chicago Tribune, April 14, 1983 Shaw's loss was attributed to his choice to endorse incumbent mayor Byrne over Harold Washington in the Democratic primary for the coinciding mayoral election. Washington won 80% of the vote in the 9th ward during the Democratic mayoral primary. Shaw was seen as having been disloyal to the black community for supporting Byrne over Washington (who was African American). Ahead of his city council runoff election, which coincided with the general election for the Chicago mayoral election, Shaw tried to align himself as a supporter of Washington's campaign.{{cite web |last1=Davis |first1=Robert |title=City council: Who will form the magic "26" |url=https://www.newspapers.com/image/387819303 |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=April 17, 1983}} Hutchison, however, had supported Washington against Byrne in the mayoral primary. During the runoff campaign, Hutchison complained of a pamphlet that was being distributed in the ward in support of Shaw's campaign that implied that Hutchison had been involved in drug trafficking.{{cite web |last1=Houston |first1=Jack |title=9th ward candidates hits 'filthy' tactics in runoff |url=https://www.newspapers.com/image/387737840 |website=Newspapers.com |publisher=Chicago Tribune |access-date=May 14, 2021 |language=en |url-access=subscription |date=March 24, 1983}}

In 1984, Shaw and his brother took up the cause of calling for legislation to be passed to require black history to be taught in public schools.

In December 1986, Shaw and his brother held a press conference in which they alleged that people were being denied care by health maintenance organizations (HMOs) for life threatening conditions.{{cite web |last1=Devall |first1=Cheryl |title=Some HMOs Accused of Failures in Crisis |url=https://www.newspapers.com/image/388946598 |via=Newspapers.com |url-access=subscription |publisher=Chicago Tribune |access-date=21 March 2024 |language=en |date=December 15, 1986}}

In 1987, Shaw defeated Hutchison to regain his old seat on the Chicago City Council. Hutchison had been indicted for taking bribes in a federal sting operation ahead of the election. For this campaign, Shaw repositioned himself as a supporter of Harold Washington. Shaw was a strong advocate in support of pay raises for members of the City Council. Shaw clashed numerous times with civil rights and community leader Jesse Jackson, who called Shaw "a hack". Harold Washington derided Shaw as a "two-bit hustler". Shaw was regarded to be a somewhat amusing personality on the council, providing interesting quotes and antics for the media to report upon.{{cite web |last1=Joravsky |first1=Ben |title=Mystery zoning: What's going down in the Ninth Ward |url=https://chicagoreader.com/news-politics/mystery-zoning-whats-going-down-in-the-ninth-ward |website=Chicago Reader |access-date=19 March 2024 |date=5 May 1988}} In 1990, John Kass of the Chicago Tribune noted that Shaw had a penchant for basking in the media attention he received, despite the media largely regarding him as clownish.

In September 1987, Shaw and fellow alderman Allan Streeter introduced a bill to remove the image of a sailing ship from the 150-year old city seal, alleging that it represented "official government sanction of slavery". Their legislation would replace the ship on the seal with a depiction of Jean Baptiste Point du Sable.{{cite web |title=Aldermen: city seal symbol is racist |url=https://www.upi.com/Archives/1987/09/03/Aldermen-city-seal-symbol-is-racist/8520557640000/?tt=3 |website=UPI |accessdate=November 18, 2020 |language=en |date=September 3, 1987}} City documents had once described the high-masted sailing ship on the seal as, "emblematic of the approach of white man's civilization and commerce".{{cite web |last1=Schmidt |first1=William E. |title=Chicago Journal; What's Wrong With City's Seal? Racism, to Some (Published 1987) |url=https://www.nytimes.com/1987/09/14/us/chicago-journal-what-s-wrong-with-city-s-seal-racism-to-some.html |website=The New York Times |accessdate=November 18, 2020 |date=September 14, 1987}} Shaw declared, "The ship represents institutionalized racism in this country." He also believed that it bore a resemblance to slave ships. Mayor Washington and a group of other black aldermen joined in support. Washington declared, speaking on the issue with the seal, "It's old, it's degrading, and it has historical baggage." It would have cost more than $1 million to replace the use of the seal. Shaw personally estimated that it would cost between $1.5 million and $2 million. The push to change the seal received criticism from some City Council members, such as Bernard Stone, who called it, "ridiculous", and Edward M. Burke who called it, "preposterous". The debate was reported to largely fall upon racial lines, with black aldermen supporting the change and white aldermen standing against it. The seal, ultimately, remained unchanged. In September 1987, Shaw also introduced a proposed ordinance that would require the Chicago Transit Authority to open its bathrooms.

After Harold Washington's death in office, Shaw joined Edward M. Burke in stopping Timothy C. Evans' bid to be appointed his mayoral successor. Eugene Sawyer instead won the vote to be Washington's successor.[https://www.ourcampaigns.com/RaceDetail.html?RaceID=385719 RaceID=385719] Shaw also called for a more thorough investigation into Washington's cause of death.{{cite web |last1=Smith |first1=Wes |title=Washington Family Calls for end to 'Insinuations' |url=https://www.chicagotribune.com/news/ct-xpm-1988-01-07-8803200598-story.html |website=chicagotribune.com |accessdate=November 18, 2020 |date=January 7, 1988}} Shaw was a chief backer of Sawyer during his mayoralty.{{cite web |title=Sawyer Allies Head for Defeat in Ward Races |url=https://www.chicagotribune.com/1988/03/16/sawyer-allies-head-for-defeat-in-ward-races |website=Chicago Tribune |access-date=19 March 2024 |date=16 March 1988}}

Shaw had a tendency to make racially inflammatory statements. In 1988, Shaw was criticized for questioning witnesses at City Council hearings about their ethnic backgrounds, and was also accused of having made antisemitic remarks about "Washington Jews". In regards to the allegations of antisemitism, Shaw, who had received his early political training from Jewish political operatives in the 24th Ward, defended himself by writing, "I have enjoyed a long and happy relationship with the Jewish community," and that, "my many Jewish friends and I am personally hurt," by the accusations of antisemitism.{{cite web |last1=Strong |first1=James |title=JEWS, SHAW AGREE TO CEASE-FIRE |url=https://www.chicagotribune.com/news/ct-xpm-1988-10-28-8802110196-story.html |website=chicagotribune.com |publisher=Chicago Tribune |date=October 28, 1988}} In 1988, Shaw also opposed a measure that would aim to stop the use of racial, ethnic, and sexual insults at committee hearings. He argued that it would infringe on the right of the council to, "protect the public interest."{{cite web |title=Chicago City Council Moves to Curb Slurs (Published 1988) |url=https://www.nytimes.com/1988/11/18/us/chicago-city-council-moves-to-curb-slurs.html |website=The New York Times |agency=Associated Press |accessdate=November 18, 2020 |date=November 18, 1988}} That same year, he also told the Chicago Defender, "A white should not be mayor. When they were mayor, they did not treat blacks and other minorities fairly. They do not know how to be fair."

Shaw utilized "aldermanic prerogative", a practice whereby alderman were given deference on zoning decisions in their wards. In 1988, on his own initiative he successfully championed downzoning for large areas in his ward.

During the mayoralty of Richard M. Daley, Shaw was a somewhat independent member of the council, giving criticism to the mayor and casting votes in opposition to his budgets. He was considered an adversary of Daley. In 1990, John Kass of the Chicago Tribune called him the, "only consistent critic of Richard Daley on the council floor." Daley and Shaw often argued with each other on the City Council Chamber floor. In one instance, Daley had Shaw's microphone turned-off, only for Shaw to continue yelling loudly at him. Shaw was reelected in 1991 and 1995.Chicago Tribune, February 28, 1991Chicago Tribune, May 18, 1993Chicago Tribune, February 3, 1995 His 1991 reelection saw him defeat Chicago Transit Authority bus driver Johnny J. O'Neal by a mere 37 votes.{{cite web |title=Three Decades of Chicago Run-Offs: Aldermanic Contests, 1987–2011 |url=https://app.chicagoelections.com/documents/general/S2015-History-Of-RunOffs-1987-Thru-2011.pdf |publisher=Chicago Board of Elections |accessdate=November 18, 2020}}{{cite web |last1=Garza |first1=Melita Marie |title=BALLOT IN 9TH GIVES VOTERS CHOICE OF 12 |url=https://www.chicagotribune.com/news/ct-xpm-1999-02-04-9902040202-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=February 4, 1999}} O'Neal would subsequently, in 1993, attempt to have the legitimacy of the vote count reinvestigated through litigation.{{cite web |last1=Fegelman |first1=Andrew |title=ALD. SHAW'S ELECTION QUESTIONED BY COURT |url=https://www.chicagotribune.com/news/ct-xpm-1993-06-24-9306240082-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=June 23, 1993}}

In 1989, Shaw opposed legislation championed by Daley to create a watchdog to oversee all of city government. The ordinance later passed, but with revisions that made aldermen exempt from the new inspector general's oversight.{{cite web |last1=Dillon |first1=Marie |title=Commentary: Tired of being lumped with all those felons? Aldermen, you know what to do |url=https://www.chicagotribune.com/opinion/commentary/ct-opinion-ethics-reform-city-council-dillon-20190723-ytzkmmbcqjazvel4zdnw5cfsmm-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=July 23, 2019}}{{cite web |title=Policing Chicago aldermen |url=https://www.chicagotribune.com/news/ct-xpm-2009-02-22-0902210321-story.html |publisher=Chicago Tribune |date=February 22, 2009}}

In 1990, Shaw proposed an ordinance to ban an AIDS awareness advertisement campaign that had seen posters placed on city transit that included same-sex couples kissing, claiming that the posters were, "promoting a lifestyle, which I object to."{{cite web |last1=Nordgren |first1=Sarah |title=AIDS Poster Being Used On Buses Sparks Controversy |url=https://apnews.com/article/2fc4dbb8eff1b9aed18943c15786dac0 |website=AP NEWS |publisher=Associated Press |accessdate=November 18, 2020 |date=August 15, 1990}} In January 1993 Shaw, joined by Dorothy Tillman, offered half-serious criticisms of former Chicago Bears coach Mike Ditka after Edward M. Burke proposed naming the 7th anniversary of the Bears' Super Bowl XX victory "Mike Ditka Day" in Chicago.{{cite web |last1=Kass |first1=John |title=2 AUDIBLE ALDERMEN BLITZ DITKA, BUT COUNCIL STILL DECIDES TO HONOR EX-COACH |url=https://www.chicagotribune.com/news/ct-xpm-1993-01-13-9303161845-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 19, 2020 |date=January 13, 1993}} In 1993, Shaw opposed Daley's nomination of Thomas Scorza to be appointed Chicago city clerk. Shaw opposed him due to testimony about improprieties in Scorza's office during his tenure as assistant U.S. Attorney.{{cite web |last1=Davis |first1=Robert |title=SHAW VOWS TO KEEP HEAT ON SCORZA |url=https://www.chicagotribune.com/news/ct-xpm-1993-06-30-9306300227-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=June 30, 1993}} Shaw raised further allegations against Scorza, without providing any evidence publicly.{{cite web |title=THE HOUNDING OF TOM SCORZA |url=https://www.chicagotribune.com/news/ct-xpm-1993-07-15-9307210345-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=July 15, 1993}}

In 1996, as part of Operation Silver Shovel, the U.S. attorney's office subpoenaed financial records from Shaw's campaign and ward funds, as well as telephone records. Before this, federal agents had unsuccessfully sought to interview Shaw.{{cite web |last1=Gibson |first1=Ray |title=SHAW CONFIRMS U.S. PROBE OF RECORDS |url=https://www.chicagotribune.com/news/ct-xpm-1996-03-06-9603060053-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 19, 2020 |date=March 6, 1996}}

After resigning to serve on the Cook County Board of Review, he backed the candidacy of his son Herbert Shaw in the 1999 election to succeed him. However, Anthony Beale, a political unknown backed by Jesse Jackson Jr. and James Meeks, defeated him in an upset.{{cite web |last1=Earley |first1=Neal |title=Beale Wins Ballot Battle — With Just Three Signatures to Spare |url=https://chicago.suntimes.com/elections/2020/1/24/21080860/beale-ballot-battle-three-signatures-9th-ward-committeeperson |website=Chicago Sun-Times |accessdate=November 18, 2020 |language=en |date=January 24, 2020}}

In 1998, Shaw was elected in the inaugural election of the newly formed Cook County Board of Review (which was a restructuring of the former Cook County Board of Appeals),{{cite web |title=History of The Board of Review |url=https://cookcountyboardofreview.com/about/history-of-the-board-of-review |website=Cook County Board Of Review |access-date=April 10, 2020 |language=en |date=May 23, 2017}} Shaw was elected in to as the commissioner from its 3rd district. He was reelected in 2002.

While on the board, Shaw was considered to be an ally of fellow board member Joseph Berrios, voting in lockstep with him on most cases.{{cite web |last1=Pallasch |first1=Asdon S. |title=Robert Shaw seeks political comeback |url=https://www.newspapers.com/image/30458105 |website=Newspapers.com |publisher=Southtown Star | agency=Sun-Times News Group |language=en |url-access=subscription |date=September 25, 2009}} On occasion, however, he did dissent in a number of cases where Berrios and the board's third member, Maureen Murphy, both voted to lower the tax rates on large properties in downtown Chicago.

During his tenure, he was dubbed the "reduction commissioner".{{cite web |last1=Keagle |first1=Lauri Harvey |title=Robert Shaw to seek assessor's seat |url=https://www.nwitimes.com/news/local/illinois/robert-shaw-to-seek-assessors-seat/article_c64c6755-4ed3-5687-a3f0-250e397d7cd1.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=June 17, 2009}} He was also criticized as handing out political and patronage favors.{{cite web |title=Cook County endorsements |url=https://www.chicagotribune.com/news/ct-xpm-2002-03-09-0203090095-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=March 9, 2002}} The Cook County state's attorney's office investigated accusations that Shaw had acted improperly by helping to arrange a property tax reduction for his brother (saving him as much as $1,219), but found no wrongdoing.{{cite web |last1=McQueary |first1=Kristen |title=Berrios and Shaw: Fetch the Bellhop for Baggage |url=https://www.newspapers.com/image/539375293 |website=Newspapers.com |publisher=Southtown Star |access-date=June 26, 2021 |language=en |url-access=subscription |date=September 24, 2009}}{{cite web |last1=Russell |first1=Gordon |agency=The Times-Picayune |publisher=NOLA.com |title=Ex-Congressman's Brother Tasted Political Victory Behind the Scenes |url=https://www.nola.com/news/ex-congressmans-brother-tasted-political-victory-behind-the-scenes/article_beaebbb8-7c92-5cd9-a881-f28312184b04.html |language=en |date=31 May 2009}} Additionally, the Board of Review made changes to its policies on reviewing tax cases in response to the fact that several of Shaw's staff members had owned properties which they analyzed themselves in their positions. Cases where Shaw's staff had done this had been flagged by fellow board member Maureen Murphy.

In 2004, Shaw was narrowly unseated in the Democratic primary by Larry Rogers Jr. Rogers had been recruited to run against Shaw by Jesse Jackson Jr. and James Meeks. Jackson had been a regular political rival of Shaw brothers.{{cite web |last1=Harvey |first1=Lauri |title=Jackson looking to oust another Shaw |url=https://www.nwitimes.com/news/local/jackson-looking-to-oust-another-shaw/article_a0f2711c-07a1-5c29-9679-087bcf3b0ebe.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 17, 2020 |language=en |date=October 19, 2003}}

In 2006, Shaw's brother William, then the mayor of Dolton, Illinois, appointed him to be city's first inspector general, a newly created position that paid $70,000 annually.{{cite web |last1=Rybarczyk |first1=Tom |title=Dolton hires mayor's brother to fight graft |url=https://www.chicagotribune.com/news/ct-xpm-2006-05-05-0605050248-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 19, 2020 |date=May 5, 2006}} The position also gave Shaw use of a city-owned car. He was confirmed to the position by the city's trustees. This move angered some in the village, who saw it as blatant nepotism.{{cite web |title=Twin brother of Dolton mayor hired to root out corruption |url=https://www.nwitimes.com/sports/twin-brother-of-dolton-mayor-hired-to-root-out-corruption/article_df335b43-0406-5f3c-9ad1-469ff51ba36a.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |agency=Associated Press |accessdate=November 18, 2020 |language=en |date=May 5, 2006}} The Better Government Association criticized this as a, "$70,000 joke on the taxpayers of Dolton". The position tasked Shaw with rooting out corruption in the village. However, village ordinance made it so that both the mayor (William Shaw) and village trustees were off-limits for investigation.{{cite web |last1=Toney |first1=Casey |title=How Dolton, Illinois Reflects America's Changing Suburbs In 2018 |url=http://ec2-204-236-225-241.compute-1.amazonaws.com/dolton/ |website=WBEZ |accessdate=November 18, 2020 |date=November 12, 2018}}

At the time he was appointed to this corruption watchdog position, federal investigators had actually been keeping an eye on Shaw himself for potential involvement in corruption in Dolton. In 2005, federal investigators discovered a practice that existed in Dolton and a number of other Chicago suburbs where politically connected citizens were allowed to carry guns and mimics of police badges. Those benefiting from this practice in Dolton had been individuals that had given notable sums of money to the campaigns of Shaw and his brother. It was discovered that at least two of those benefiting from this were drug smugglers that had used the mimicry police IDs in order to avoid having police search their vehicles.

In 2006, Shaw was criticized for flashing a handgun while personally conducting a traffic stop of an alleged drug dealer.

Shaw would remain in this position through the launch of his Cook County assessor campaign in late 2009.

For more than a quarter century, Shaw and his brother William were dominant political "kingmakers" of Chicago's far South Side and southern suburbs. They garnered the support of the African American electorate in the area. Over the years, their main rivals for influence there was the Jackson family, Jesse Jackson and Jesse Jackson Jr. Their influence dissipated greatly in the late 1990s and the early 2000s, with Jesse Jackson Jr. largely beating them out to become the new kingmaker at the time.{{cite web |last1=Joravsky |first1=Ben |title=By Any Means Necessary |url=https://www.chicagoreader.com/chicago/by-any-means-necessary/Content?oid=910204 |website=Chicago Reader |accessdate=November 18, 2020 |language=en |date=October 31, 2002}}{{cite web |last1=Janega |first1=James |title=Meeks inherits a battle |url=https://www.chicagotribune.com/news/ct-xpm-2002-07-31-0207310328-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 19, 2020 |date=July 31, 2002}}{{cite web |title=Dolton didn't want to be engulfed |url=https://www.newspapers.com/image/237187510 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 28, 2021 |language=en |url-access=subscription |date=May 20, 2009}} Their tide first began to change when Jesse Jackson Jr. won election to U.S. congress in 1996, defeating the Shaw brothers-backed candidate Emil Jones in the Democratic primary. In 1999, Jackson Jr. successfully backed Anthony Beale against Shaw's son Herbert Shaw in the race to succeed Shaw as 9th Ward alderman. In 2000, Jackson Jr. backed David E. Miller in his successful state representative Democratic primary race against Shaw-backed candidate Willis Harris. In 2002, Jackson Jr. encouraged James Meeks to make his successful general election challenge to William Shaw for state senate. Jackson accused the Shaw brothers, that same year, of being behind the dummy candidate campaign of a retired truck driver named Jesse L. Jackson against him for congress.{{cite web |last1=Ciokajlo |first1=Mickey |title=Tax turmoil, feud spotlight Shaw bid |url=https://www.newspapers.com/image/235809787 |website=Newspapers.com |publisher=Chicago Tribune |language=en |url-access=subscription |date=February 26, 2004}} In 2004, Jackson backed Larry Rogers Jr.'s successful primary challenge against Shaw for Cook County Board of Review. Also in 2004, the Shaw brothers denied involvement with two challengers running against Jackson for congress, who each filed challenges to the younger Jackson's petition signatures (which, if successful, would have seen Jackson removed from the ballot in the Democratic primary). The two challengers to Jackson worked for Dolton (where William Shaw was mayor), and used the village's attorney as their lawyer. By 2006, the Shaw brothers leveraged a Dolton public-access television program to regularly assail Jesse Jackson Jr.{{cite web |title=Dolton Mayor William 'Bill' Shaw dies |url=https://www.chicagotribune.com/2008/11/27/dolton-mayor-william-bill-shaw-dies/ |website=Chicago Tribune |access-date=19 March 2024 |date=27 November 2008}}{{cite web |title=Dolton mayor uses TV to criticize rivals |url=https://qconline.com/news/illinois/dolton-mayor-uses-tv-to-criticize-rivals/article_d8dfc51d-63ab-515f-8ed7-dee5abf67921.html |website=Dispatch Argus |agency=The Associated Press |access-date=19 March 2024 |language=en |date=31 July 2006}}

When the Shaw brothers ran the 9th Ward Regular Democratic Organization, they and their campaign volunteers helped deliver strong voter support for campaigns of African American politicians such as Mayor Harold Washington and Illinois State Senator Emil Jones, and the 1992 U.S. Senate campaign of Carol Moseley Braun. They also helped mobilize support in the area for the 2004 U.S. Senate campaign of Barack Obama.

In 1996, Shaw was elected the 9th Ward Democratic committeeman, succeeding his brother William in holding this elected Democratic Party leadership position.{{cite web |title=Official Final Results Primary Election Cook County, Illinois Tuesday, March 19, 1996 |url=https://www.cookcountyclerk.com/sites/default/files/pdfs/March1996.pdf|website=www.cookcountyclerkil.com |accessdate=October 15, 2020}}{{cite web |title=Official Final Results Primary Election Cook County, Illinois Tuesday, MARCH 15, 1988 |url=http://www.voterinfonet.com/results/archive/1988MarCombinedSummary.pdf |website=voterinfo.net |publisher=Cook County Clerk |archiveurl=https://web.archive.org/web/20081003205700/http://www.voterinfonet.com/results/archive/1988MarCombinedSummary.pdf |archivedate=October 3, 2008}}{{cite web |title=Official Final Results Primary Election Cook County, Illinois Tuesday, March 17, 1992 |url=https://www.cookcountyclerk.com/sites/default/files/pdfs/March1992.pdf |website=www.cookcountyclerkil.com |archive-url=https://web.archive.org/web/20211011045101/https://www.cookcountyclerkil.gov/sites/default/files/pdfs/March1992.pdf |archive-date=October 11, 2021 |accessdate=October 15, 2020}} In 2000, Shaw was unseated by Anthony Beale.{{cite web |title=Official Final Results Primary Election Cook County, Illinois Tuesday, March 21, 2000 |url=https://www.cookcountyclerk.com/sites/default/files/2000MarchCombinedSUMMARY.pdf |publisher=Cook County Clerk |accessdate=June 23, 2020}}

Among the individuals that got their starts in the political organization run by the Shaw brothers was Mose Jefferson.{{cite web |title=Five Things You Don't Know About the Southland |url=https://www.newspapers.com/image/538610147 |website=Newspapers.com |publisher=Southtown Star |access-date=June 28, 2021 |language=en |url-access=subscription |date=December 18, 2009}}{{cite web |last1=Russell |first1=Gordon |title=Ex-congressman's brother tasted political victory behind the scenes |url=https://www.nola.com/news/ex-congressmans-brother-tasted-political-victory-behind-the-scenes/article_beaebbb8-7c92-5cd9-a881-f28312184b04.html |website=NOLA.com |agency=The Times-Picayune |access-date=19 March 2024 |language=en |date=31 May 2009}}

After Shaw's death, the Chicago Crusader credited him and his brother's political organization with successfully pushing the Illinois State Legislature to establish new Cook County Circuit Court and Illinois Appellate Court sub-circuits located in African American city wards, which the Chicago Crusader wrote had the impact of enabling more than 60 African American individuals to become judges.{{cite web |title=Former Chicago Alderman and Cook County Commissioner Robert Shaw Succumbs at Age 83 To Cancer |url=https://chicagocrusader.com/former-chicago-alderman-and-cook-county-commissioner-robert-shaw-succumbs-at-age-83-to-cancer/ |website=Chicago Crusader |access-date=15 February 2024 |date=22 July 2021}}

In 1984, Shaw was one of four individuals who challenged incumbent U.S. congressman Gus Savage in the Democratic primary for Illinois's 2nd congressional district. Other challengers included state senators Glenn Dawson and James C. Taylor.{{cite web |title=Our Campaigns – IL District 2 – D Primary Race – Mar 20, 1984 |url=https://www.ourcampaigns.com/RaceDetail.html?RaceID=389374 |website=www.ourcampaigns.com |publisher=Our Campaigns |accessdate=November 17, 2020}} Savage won renomination, with Shaw placing fourth.{{cite book |title=State of Illinois OFFICIAL VOTE Cast at the GENERAL PRIMARY ELECTION MARCH 20, 1984 |year=1966 |publisher=Illinois State Board of Elections |location=Springfield, Illinois |page=163 |url=https://archive.org/details/stateofillinoiso1984illi |access-date=October 20, 2020}}

In October 2004, Shaw announced that he would be challenging incumbent village president (mayor) Don DeGraff in the April 2005 South Holland, Illinois, election.{{cite web |last1=Sadovi |first1=Carlos |title=Veteran politician Shaw runs for mayor in South Holland |url=https://www.chicagotribune.com/news/ct-xpm-2004-10-25-0410250131-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=October 25, 2004}} Shaw had moved from the Hyde Park neighborhood of Chicago to the southern suburb in 1999, shortly after he left the Chicago City Council. Shaw was defeated in an immense landslide, with DeGraff receiving 91% of the vote, to Shaw's 6%.{{cite web |last1=McCollum |first1=Carmen |title=DeGraff to stay in South Holland |url=https://www.nwitimes.com/news/local/degraff-to-stay-in-south-holland/article_c2ba99da-a4ff-5fc2-ab91-0bcfef92e64f.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=April 6, 2005}}

During his campaign, Shaw pledged to bring more business and job opportunities to the village, if elected. The village had a 10% unemployment rate at the time.

During the campaign, Shaw accused incumbent mayor DeGraff, who was white, of preventing more minorities from working for the village by utilizing the village's residency policy, which allowed village employees, with the exception of department heads and their deputies, to reside outside of the village.{{cite web |last1=Ziemba |first1=Stanley |title=South Holland mayor to seek re-election |url=https://www.newspapers.com/image/231339495 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 28, 2021 |language=en |url-access=subscription |date=November 5, 2004}} Shaw proposed making residency in the village a requirement for all village employees.{{cite web |last1=Mitchell |first1=David |title=SHAW TO RUN FOR MAYOR IN S. HOLLAND |url=https://www.newspapers.com/image/307148340 |website=Newspapers.com |publisher=The Times (Munster, Indiana) |access-date=June 29, 2021 |language=en |url-access=subscription |date=October 23, 2004}}

Shaw tried to characterize DeGraff as an "ultraconservative". Shaw claimed that DeGraff was a supporter of heavily conservative politician Alan Keyes, who had been the Republican Party nominee who ran against Democrat Barack Obama in the 2004 United States Senate election in Illinois. DeGraff refuted this by pointing out that he had supported Obama's campaign for the United States Senate.{{cite web |last1=Shalka |first1=Jennifer |title=Shaws try for twin victories |url=https://www.newspapers.com/image/235978420 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 29, 2021 |language=en |url-access=subscription |date=March 30, 2005}} Shaw charged that DeGraff practiced nepotism as mayor.{{cite web |last1=Mitchell |first1=David |title=Shaw charges nepotism in South Holland administration |url=https://www.newspapers.com/image/306550741 |website=Newspapers.com |publisher=The Times (Munster, Indiana) |access-date=June 29, 2021 |language=en |url-access=subscription |date=November 20, 2004}} DeGraff denied that the allegations were true.{{cite web |last1=Mitchell |first1=David |title=Nepotism |url=https://www.newspapers.com/image/306550764 |website=Newspapers.com |publisher=The Times (Munster, Indiana) |access-date=June 29, 2021 |language=en |url-access=subscription |date=November 20, 2004}} Businesses that Shaw alleged DeGraff was personally profiting from awarding contracts to either did not have any connection to DeGraff, or had not even received municipal contracts in South Holland.{{cite web |last1=Kiesling |first1=Mark |title=Shaw plays the name game and loses |url=https://www.newspapers.com/image/306340459 |website=Newspapers.com |publisher=The Times (Munster, Indiana) |language=en |url-access=subscription |date=January 9, 2005}}

A victory by Shaw would have helped to reestablish the Shaw brothers' declining political influence in the southern part of the Chicago area.{{cite web |title=Mayors: Longtime clerk is 'clobbered' in Oak Lawn |url=https://www.newspapers.com/image/231441299 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 29, 2021 |language=en |url-access=subscription |date=April 6, 2005}} Ahead of the election, commenting on Shaw's campaign in South Holland and his brother's coinciding reelection campaign in neighboring Dolton, Jennifer Shalka of the Chicago Tribune wrote, "a double win would give the Shaws their own fiefdom. Dolton and South Holland have a total of about 50,000 residents." Political rival Jesse Jackson Jr. supported DeGraff in Shaw's race, and also supported an unsuccessful challenger to Shaw's brother William in the Dolton election.

In 2006, Shaw ran for the Democratic nomination for the 29th district seat in the Illinois House of Representatives, seeking to unseat incumbent David E. Miller.{{cite web |last1=Harvery |first1=Lauri |title=Accusations, arrest dominate 29th District race |url=https://www.nwitimes.com/news/local/accusations-arrest-dominate-29th-district-race/article_81f19411-39e1-52ec-a2fe-903f0faf27cc.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=November 17, 2020}} He was unsuccessful, losing to Miller by 70.88% to 29.12%.{{cite web |title=Election Results Information |url=https://www.elections.il.gov/ElectionOperations/ElectionResults.aspx |website=www.elections.il.gov |publisher=Illinois State Board of Elections |accessdate=November 18, 2020 |archive-date=February 26, 2021 |archive-url=https://web.archive.org/web/20210226202545/https://elections.il.gov/ElectionOperations/ElectionResults.aspx |url-status=dead }}

The campaign was seen as another effort by Shaw to stop the decline of his and his brother's political power in Chicago's suburbs. Political observers saw Shaw as unlikely to succeed, however.{{cite web |last1=Ziemba |first1=Stanley |title=LESGISLATORS: Shaw, Durkin are seeking comebacks |url=https://www.newspapers.com/image/231645634 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 30, 2021 |language=en |url-access=subscription |date=March 8, 2006}} This was another saga in the Shaw brothers' political rivalry with Jesse Jackson Jr., as Miller was considered Jackson's "point man" in the Illinois House of Representatives on matters such as education reform and the proposed Chicago south suburban airport. Jackson gave his backing to Miller in the election.

Shaw ran for Cook County assessor in 2010. If elected, he would have been the first African American holder of the office. In January 2010, the Chicago Reader reported that Shaw's campaign lacked not only a website, but also lacked a campaign office and phone number.{{cite web |last1=Joravsky |first1=Ben |title=Who'll Keep Your Rent Down Now? |url=https://www.chicagoreader.com/chicago/joe-berrios-raymond-figueroa-robert-shaw-cook-county-assessor-election/Content?oid=1317832 |website=Chicago Reader |accessdate=November 19, 2020 |language=en |date=January 14, 2010}} During the campaign, Shaw trained his criticisms at opponent Joseph Berrios, and largely ignored his other opponent, Raymond A. Figueroa.{{cite web |last1=Dadick |first1=Hal |last2=Becker |first2=Robert |title=Berrios says his foes are attacking him |url=https://www.newspapers.com/image/237218715 |website=Newspapers.com |publisher=Chicago Tribune |language=en |url-access=subscription |date=December 29, 2009}} Since soon after incumbent assessor James Houlihan announced that he would not seek reelection, Berrios had been considered the front-runner in the race to succeed him.

Shaw placed second out of three candidates in the Democratic primary, with 34.09% of the vote, with the winner of the primary, Berrios, receiving 39.14% of the vote.{{cite web |title=Combined Summary Report – Primary Election Cook County Primary February 2, 2010 |url=https://www.cookcountyclerk.com/sites/default/files/Combined%20Summary_Final.pdf |publisher=Cook County Clerk's Office |accessdate=March 16, 2020 |archive-date=October 13, 2020 |archive-url=https://web.archive.org/web/20201013204759/https://www.cookcountyclerk.com/sites/default/files/Combined%20Summary_Final.pdf |url-status=dead }} Shaw had placed first in 19 of the 20 wards in Chicago with the most sizeable black populations.{{cite web |last1=Stewart |first1=Russ |title=Political Analyst – Article September 29, 2010 |url=http://www.russstewart.com/articles/2010/09-29-2010.html |website=www.russstewart.com |publisher=Russ Stewart |date=September 29, 2010}}

In December 2013, Shaw moved from South Holland, Illinois, where he had lived since 1999, to the Hyde Park–Kenwood area of Chicago. In March 2014, Shaw announced he would run in the 2015 Chicago mayoral election. He was the first noteworthy politician to announce that they would be challenging incumbent mayor Rahm Emanuel, and second challenger to announce, after Amara Enyia. However, he ultimately withdrew his candidacy.{{cite web |last1=Seidel |first1=Jon |title=Former Ald. Robert Shaw to run for mayor |url=https://chicago.suntimes.com/city-hall/2014/3/13/18539458/former-ald-robert-shaw-to-run-for-mayor |website=Chicago Sun-Times |accessdate=November 18, 2020 |language=en |date=March 13, 2014}}{{cite web |title=Can Robert Shaw Beat Rahm Emanuel in 2015? |url=https://www.nbcchicago.com/news/local/whos-running-against-rahm/74896/ |website=NBC Chicago |publisher=WMAQ-TV |accessdate=November 18, 2020 |date=March 13, 2014}}{{cite web|url=http://chicago.cbslocal.com/2014/11/24/nine-candidates-file-to-challenge-mayor-emanuel/|title=Nine Candidates File To Challenge Mayor Emanuel|work=CBS Chicago|date=November 24, 2013|accessdate=November 26, 2014}}{{cite web|url=http://www.dnainfo.com/chicago/20140411/near-west-side/chicago-cop-running-for-mayor-says-he-would-fire-mccarthy-byrd-bennett|title=City Police Officer Running for Mayor Says He'd Fire McCarthy, Byrd-Bennett|work=DNA Info Chicago|date=April 11, 2014|accessdate=May 13, 2014|url-status=dead|archiveurl=https://web.archive.org/web/20140516160028/http://www.dnainfo.com/chicago/20140411/near-west-side/chicago-cop-running-for-mayor-says-he-would-fire-mccarthy-byrd-bennett|archivedate=May 16, 2014}}{{cite web|url=http://www.suntimes.com/26178348-761/former-ald-robert-shaw-announces-run-for-mayor.html|title=Former Ald. Robert Shaw announces run for mayor|work=Chicago Sun-Times|date=March 13, 2014|accessdate=March 31, 2014}}[http://www.chicagobusiness.com/article/20141230/BLOGS02/141229904/dozens-quit-or-knocked-off-ballot-in-city-hall-races Dozens quit or knocked off ballot in City Hall races] Crain's Chicago Business. December 30, 2014. Accessed December 30, 2014[http://www.chicagotribune.com/news/ct-chicago-mayors-race-met-1231-20141230-story.html Garcia seeks support among black voters in Chicago mayor's race] Chicago Tribune. December 30, 2014. Accessed December 30, 2014

In the previous 2011 mayoral election, Shaw had been an advisor to the campaign of Carol Moseley Braun.{{cite web |title=Ex-alderman Robert Shaw to run for Chicago mayor |url=https://thesouthern.com/news/local/state-and-regional/ex-alderman-robert-shaw-to-run-for-chicago-mayor/article_7cd88cda-2406-5b94-b7dd-dd1aa436554b.html |website=The Southern Illinosian |publisher=The Associated Press |accessdate=November 18, 2020 |language=en |date=March 13, 2014}}

During his candidacy, he took positions, including supporting a move to having the Chicago Board of Education be an elected school board.{{cite web |last1=Hutson |first1=Wendell |last2=Cox |first2=Ted |title=Former Alderman Robert Shaw Running For Mayor |url=https://www.dnainfo.com/chicago/20140313/chicago/former-alderman-robert-shaw-running-for-mayor/ |website=DNAinfo Chicago |accessdate=November 18, 2020 |format=March 13, 2014 |archive-date=September 24, 2020 |archive-url=https://web.archive.org/web/20200924124851/https://www.dnainfo.com/chicago/20140313/chicago/former-alderman-robert-shaw-running-for-mayor/ |url-status=dead }} He criticized Emanuel for public school closures.{{cite web |last1=Tejeda |first1=Gregory Tejeda |title=Robert Shaw leaves south suburbs, wants to run for Chicago mayor |url=https://www.nwitimes.com/news/local/illinois/robert-shaw-leaves-south-suburbs-wants-to-run-for-chicago-mayor/article_6350a1dc-ed9f-52c1-8e9d-a53dbfa460c4.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=March 13, 2014}} He also voiced concern of the city's ability to fund pension programs for municipal employees, criticizing cutting benefits for retired workers. He pledged to rectify both previously-implemented school closings and decreases of benefits for retired municipal employees.

He described his campaign strategy as aiming to bring together a coalition of African Americans, Latinos, and others displeased with the policies of the incumbent mayor. He stated he believed that he had strength as a contender, saying that he believed he had strong name recognition. During his candidacy, an early July 2014 poll taken by We Ask America showed that, in a head-to-head matchup, incumbent mayor Rahm Emanuel led him 47.7% to 29.6%, with 22.8% of voters being undecided.{{cite web |last1=Koreki |first1=Natasha |title=Exclusive poll: Karen Lewis could give Rahm run for his money {{!}} Early & Often |url=http://politics.suntimes.com/article/chicago/exclusive-poll-karen-lewis-could-give-rahm-run-his-money/mon-07142014-334pm |website=politics.suntimes.com |publisher=Chicago Sun-Times |archiveurl=https://web.archive.org/web/20140715045352/http://politics.suntimes.com/article/chicago/exclusive-poll-karen-lewis-could-give-rahm-run-his-money/mon-07142014-334pm |archivedate=July 15, 2014 |date=July 14, 2014}} Shaw's campaign had very low funds.{{cite web |last1=Stewart |first1=Russ |title=Political Analyst – Article November 5, 2014 |url=http://www.russstewart.com/articles/2014/11-05-2014.html |website=www.russstewart.com |publisher=Russ Stewart |accessdate=November 19, 2020 |date=November 5, 2014}}

After dropping out, Shaw endorsed Willie Wilson in the election.{{cite web |last1=says |first1=Diane |title=Mayoral Face Off |url=https://southsideweekly.com/mayoral-face-off/ |publisher=South Side Weekly |accessdate=November 21, 2019 |date=February 17, 2015}}{{cite web |title=Willie Wilson gains Cook Co. Commissioner Robert Shaw's support in mayor's race |url=https://abc7chicago.com/willie-wilson-chicago-board-of-elections-election-signatures/454590/ |website=ABC7 Chicago |accessdate=November 18, 2020 |language=en |date=December 29, 2014}} Shaw would go on to again support Wilson in his 2019 mayoral campaign as well, taking part in his March 2018 campaign announcement.{{cite web |last1=Strausberg |first1=Chinta |title=Dr. Willie Wilson throws hat into mayoral ring {{!}} The Crusader Newspaper Group |url=https://chicagocrusader.com/dr-willie-wilson-throw-hat-into-mayoral-ring/ |website=chicagocrusader.com |publisher=Chicago Crusader |accessdate=November 19, 2020 |date=March 29, 2018}}

Shaw was a candidate in 2016 in the Democratic primary for the Metropolitan Water Reclamation District of Greater Chicago board. He withdrew his candidacy before the election, however.{{cite web |title=This Time As Democrat, Capparelli Eyes MWRD Seat |url=https://www.journal-topics.com/articles/this-time-as-democrat-capparelli-eyes-mwrd-seat/ |website=Journal Online |publisher=Journal & Topics |accessdate=November 18, 2020 |date=January 27, 2016}} He declared again to run in 2018,{{cite web |last1=Stewart |first1=Russ |title=2018 MWRD contests bring chaos-as-usual |url=http://nadignewspapers.com/2017/12/22/2018-mwrd-contests-bring-chaos-as-usual/ |website=Nadig Newspapers – Northwest Side Local Newspapers |accessdate=November 18, 2020 |date=December 22, 2017}}{{cite tweet |user=ILElectionData |number=937767711907680257 |date=December 4, 2017 |title=Cook County notes: former State Rep Eddie Acevedo has filed for Sheriff, former Chicago Alderman and Cook County Board of Review member Robert Shaw has filed for MWRD. }} but was ultimately disqualified from appearing on the ballot.{{cite web |title=Robert Shaw (Illinois) |url=https://ballotpedia.org/Robert_Shaw_(Illinois) |website=Ballotpedia |accessdate=November 18, 2020 |language=en}}

In 2021, Shaw ran unsuccessfully for the mayoral office once held by his brother in Dolton, Illinois. He placed last out of four candidates in the Democratic Party primary, receiving six percent of the vote.{{cite web |title=Tiffany Henyard Wins Race For Mayor Of Dolton |url=https://www.cbsnews.com/chicago/news/tiffany-henyard-wins-race-for-mayor-of-dolton/ |publisher=CBS Chicago |website=cbsnews.com |access-date=8 February 2024 |date=6 April 2021}} His opponents were incumbent mayor Riley Rogers and village trustees Tiffany Henyard and Andrew Holmes. {{cite web |title=Tiffany Henyard Declares Victory In Dolton Democratic Mayoral Primary |url=https://www.cbsnews.com/chicago/news/tiffany-henyard-declares-victory-in-dolton-democratic-mayoral-primary/ |website=cbsnews.com |publisher=CBS Chicago |access-date=1 March 2024 |date=23 February 2021}} Shaw endorsed the primary's victor, Henyard, in the general election.{{cite web |last1=Jones |first1=Tim Carol |title=Dolton Mayoral Candidate Eying Victory |url=https://citizennewspapergroup.com/news/2021/mar/17/dolton-mayoral-candidate-eyeing-victory/ |website=citizennewspapergroup.com |publisher=The Weekly Citizen |access-date=1 March 2024 |date=March 17, 2021}} Henyard won the general election.

Shaw fathered two sons and four daughters.{{cite web |title=Cook County 3rd District Board of Review seat |url=https://www.newspapers.com/image/538423852 |website=Newspapers.com |publisher=Southtown Star |access-date=June 28, 2021 |language=en |url-access=subscription |date=March 7, 2004}} In 1997, Shaw's 27-year-old son John was murdered by gunshots near his South Side Chicago house.{{cite web |last1=Becker |first1=Robert |title=CONVICTION THROWN OUT IN '97 MURDER OF SHAW'S SON |url=https://www.chicagotribune.com/news/ct-xpm-1999-12-24-9912240202-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=December 24, 1999}}{{cite web |last1=Deardorff |first1=Julie |last2=Buchanan |first2=Andrew |title=ALD. SHAW'S SON IS SHOT TO DEATH |url=https://www.chicagotribune.com/news/ct-xpm-1997-01-06-9701060112-story.html |website=chicagotribune.com |publisher=Chicago Tribune |accessdate=November 18, 2020 |date=January 6, 1997}} From 1999 until 2013, Shaw lived in South Holland, Illinois. In December 2013, he moved to the Hyde Park–Kenwood area of Chicago.

At the peak of their political careers, Shaw and his brother were recognizable-looking for both wearing similar hairpieces.

In December 2008, in Dolton, Shaw, then still the village's inspector general, alleged that he had been assaulted in an altercation with corrections officer Elliott R. Kozel, who was circulating a petition in support of mayoral candidate Riley Rogers (the nephew of Larry Rogers, who had unseated Shaw on the Cook County Board of Review).{{cite web |title=Politics Gets Rough in Dolton. Literally. |url=https://chicagoist.com/2008/12/07/politics_gets_rough_in_dolton_liter.php |website=The Chicagoist |accessdate=November 18, 2020 |date=December 7, 2008 |archive-date=November 5, 2017 |archive-url=https://web.archive.org/web/20171105181307/http://chicagoist.com/2008/12/07/politics_gets_rough_in_dolton_liter.php |url-status=dead }}{{cite web |title=Arrests made after possible political scuffle in Dolton |url=https://abc7chicago.com/archive/6542281/ |website=abc7chicago.com |publisher=WLS-TV |accessdate=November 18, 2020 |date=December 7, 2008}} The assault charges against Rogers were dismissed by a Cook County judge on February 18, 2009.{{cite web |title=Judge throws out assault charges |url=https://www.newspapers.com/image/232462047 |website=Newspapers.com |publisher=Chicago Tribune |access-date=June 26, 2021 |language=en |url-access=subscription |date=February 19, 2009}} In February 2012, Shaw was hospitalized after he fell and injured himself in his house. His injuries included a fractured nose.{{cite web |title=Robert Shaw hospitalized after fall |url=https://chicago.suntimes.com/news/2012/2/21/18533454/robert-shaw-hospitalized-after-fall |website=Chicago Sun-Times |accessdate=November 18, 2020 |language=en |date=February 21, 2012}}{{cite web |title=Longtime South Holland politician Robert Shaw recuperating after fall |url=https://www.nwitimes.com/news/local/illinois/south-holland/longtime-south-holland-politician-robert-shaw-recuperating-after-fall/article_4394aedf-9e17-556d-adfd-40fb46f2d7c6.html |website=nwitimes.com |publisher=The Times of Northwest Indiana |accessdate=November 18, 2020 |language=en |date=February 21, 2012}}

Shaw contracted COVID-19 in 2021 during the COVID-19 pandemic, managing to overcome the viral infection.

Shaw died at the age of 83 of cancer on July 22, 2021 at a rehabilitation facility in South Holland, Illinois.{{cite web |last1=O'Donnell |first1=Maureen |title=Robert Shaw dies at 83; was Chicago alderman, member of Cook County Board of Review |url=https://chicago.suntimes.com/2021/7/22/22588810/robert-shaw-obituary-dies-83-chicago-alderman-cook-county-board-review-assessments |website=Chicago Sun-Times |access-date=August 9, 2021 |language=en |date=July 22, 2021}} He was survived by a daughter and two sons.

{{Election box begin no party no change| title= 1975 Chicago 9th Ward aldermanic election{{cite web |title=Aldermanic Results |url=https://www.newspapers.com/image/383894673 |website=Newspapers.com |publisher=Chicago Tribune |access-date=March 8, 2021 |language=en |url-access=subscription |date=February 26, 1975}}}}

{{Election box winning candidate no party no change

|candidate = Alexander Adducci (incumbent)

|votes = 5,194

|percentage = 56.02

}}

{{Election box candidate no party no change

|candidate = Robert Shaw

|votes = 1,963

|percentage = 21.17

}}

{{Election box candidate no party no change

|candidate = Perry Hutchison

|votes = 1,799

|percentage = 19.40

}}

{{Election box candidate no party no change

|candidate = Salim Al-Nurridin

|votes = 315

|percentage = 3.40

}}

{{Election box total no party no change

| votes = 9,271

| percentage = 100

}}

{{Election box end}}

{{Election box begin no party no change| title= 1995 Chicago 9th Ward aldermanic election{{cite web |title=Chicago Democracy Project – Election Results |url=http://chicagodemocracy.org/ElectionResults.jsp?election=crdd_primary%2Cgis_entity_crdd_1995_Primary_Election%2Cil_chi_ald_9_npald |website=chicagodemocracy.org |publisher=Chicago Democracy Project |accessdate=November 19, 2020}}}}

{{Election box winning candidate no party no change

|candidate = Robert Shaw (incumbent)

|votes = 5,634

|percentage = 61.37

}}

{{Election box candidate no party no change

|candidate = Cora L. Mcgruder

|votes = 2,686

|percentage = 29.26

}}

{{Election box candidate no party no change

|candidate = John J. O'Neal

|votes = 861

|percentage = 9.38

}}

{{Election box total no party no change

|votes = 9,181

|percentage = 100

}}

{{Election box end}}

;1998

{{Election box begin no change | title=1998 Cook County Board of Review 3rd district Democratic primary{{cite web |title=OFFICIAL FINAL RESULTS PRIMARY ELECTION COOK COUNTY, ILLINOIS TUESDAY, MARCH 17, 1998 |url=https://www.cookcountyclerk.com/sites/default/files/March1998.pdf |website=www.cookcountyclerkil.com |accessdate=October 15, 2020}}}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 175,973

|percentage = 84.81

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Arvin Boddie

|votes = 31,514

|percentage = 15.19

}}

{{Election box total no change

| votes = 207,487

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=1998 Cook County Board of Review 3rd district election{{cite web |title=OFFICIAL FINAL RESULTS GENERAL ELECTION COOK COUNTY, ILLINOIS TUESDAY, NOVEMBER 3, 1998 |url=https://results.cookcountyclerkil.gov/electionresults/110398/1998NovemberCombinedSUMMARY.pdf |website=results.cookcountyclerkil.gov }}}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 406,862

|percentage = 100

}}

{{Election box total no change

| votes = 406,862

| percentage = 100

}}

{{Election box end}}

;2002

{{Election box begin no change | title=2002 Cook County Board of Review 3rd district Democratic primary{{cite web |title=OFFICIAL FINAL RESULTS COOK COUNTY, ILLINOIS PRIMARY ELECTION TUESDAY, MARCH 19, 2002 DEMOCRATIC PRIMARY |url=https://www.cookcountyclerk.com/sites/default/files/2002MarchCombinedSUMMARY.pdf |publisher=Cook County, Illinois |accessdate=June 22, 2020 |archive-date=June 22, 2020 |archive-url=https://web.archive.org/web/20200622124859/https://www.cookcountyclerk.com/sites/default/files/2002MarchCombinedSUMMARY.pdf |url-status=dead }}}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw (incumbent)

|votes = 143,317

|percentage = 51.71

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Steven Burris

|votes = 133,854

|percentage = 48.29

}}

{{Election box total no change

| votes = 277,171

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=2002 Cook County Board of Review 3rd district election{{cite web |title=TABULATED STATEMENT OF THE RETURNS AND PROCLAMATION OF THE RESULTS OF THE CANVASS OF THE ELECTION RETURNS FOR THE GENERAL ELECTION HELD IN EACH OF THE PRECINCTS IN ALL THE WARDS IN THE CITY OF CHICAGO ON TUESDAY, NOVEMBER 5, 2002 A.D. |url=https://app.chicagoelections.com/documents/proclamations/Proc-2002-11-05.pdf |publisher=Chicago Board of Election Commissioners |accessdate=June 18, 2020}}{{cite web |title=SUBURBAN COOK COUNTY RESULTS |url=http://www.voterinfonet.com/results/11502results/ |website=voterinfonet.com |publisher=Cook County Clerk |archiveurl=https://web.archive.org/web/20050209124209/http://www.voterinfonet.com/results/11502results/ |archivedate=February 9, 2005 |url-status=dead}}}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw (incumbent)

|votes = 374,527

|percentage = 100

}}

{{Election box total no change

| votes = 374,527

| percentage = 100

}}

{{Election box end}}

;2004

{{Election box begin no change | title=2004 Cook County Board of Review 3rd district Democratic primary{{cite web |title=OFFICIAL SUMMARY REPORT COOK COUNTY, ILLINOIS PRIMARY ELECTION TUESDAY, MARCH 16, 2004 STATISTICS |url=https://www.cookcountyclerk.com/sites/default/files/2004MarchCookSUMMARY.pdf|publisher=Cook County Clerk's Office |accessdate=March 19, 2020}}{{cite web |title=TABULATED STATEMENT OF THE RETURNS AND PROCLAMATION OF THE RESULTS OF THE CANVASS OF THE ELECTION RETURNS FOR THE GENERAL ELECTION IN EACH OF THE PRECINCTS IN ALL THE WARDS IN THE CITY OF CHICAGO ON TUESDAY, MARCH 16, 2004 A.D.|url=https://app.chicagoelections.com/documents/proclamations/Proc-2004-03-16.pdf|publisher=Chicago Board of Elections |accessdate=March 19, 2020}}

}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Larry R. Rogers Jr.

|votes = 148,987

|percentage = 50.18

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw (incumbent)

|votes = 147,900

|percentage = 49.81

}}

{{Election box total no change

| votes = 296,887

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=1996 9th Ward Democratic Committeeman election

}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 6,539

|percentage = 100

}}

{{Election box total no change

| votes = 6,539

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=2000 9th Ward Democratic Committeeman election}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Anthony A. Beale

|votes = 6,642

|percentage = 65.05

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw (incumbent)

|votes = 3,185

|percentage = 31.19

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Valeria Smith

|votes = 244

|percentage = 2.39

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Reginald B. Williams, Sr.

|votes = 105

|percentage = 1.03

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Michael L. Miguest

|votes = 34

|percentage = 0.33

}}

{{Election box total no change

| votes = 6,539

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=2010 Cook County Assessor Democratic primary}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Joseph Berrios

|votes = 203,397

|percentage = 39.14

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 177,155

|percentage = 34.09

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Raymond A. Figueroa

|votes = 139,164

|percentage = 26.78

}}

{{Election box total no change

| votes = 519,716

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change | title=2006 Illinois's House of Representatives 29th district Democratic primary}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = David E. Miller (incumbent)

|votes = 9,942

|percentage = 70.88

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 4,085

|percentage = 29.12

}}

{{Election box total no change

| votes = 14,027

| percentage = 100

}}

{{Election box end}}

{{Election box begin no party no change | title=2005 South Holland Village President election{{cite web |title=Suburban Cook County Election Results |url=https://results.cookcountyclerkil.gov/electionresults/040505/SummaryElection040505RaceNum431.html?Party=ALL |website=results.cookcountyclerkil.gov |accessdate=November 18, 2020}}

}}

{{Election box winning candidate no party no change

|party = Democratic Party (United States)

|candidate = Don A. De Graff (incumbent)

|votes = 6,761

|percentage = 91.86

}}

{{Election box candidate no party no change

|candidate = Robert Shaw

|votes = 456

|percentage = 6.20

}}

{{Election box candidate no party no change

|candidate = Angela Thomas-Lots

|votes = 143

|percentage = 1.94

}}

{{Election box total no party no change

| votes = 7,360

| percentage = 100

}}

{{Election box end}}

{{Election box begin no change|title=2021 Dolton mayoral Democratic primary election{{Cite web |date=2021-02-23 |title=February 23, 2021 Consolidated Primary Election - Mayor, Village of Dolton Township & Precinct Results |url=https://results221.cookcountyclerkil.gov/Detail.aspx?eid=22321&rid=13&vfor=1&twpftr=0 |url-status=live |archive-url=https://web.archive.org/web/20231227062720/https://results221.cookcountyclerkil.gov/Detail.aspx?eid=22321&rid=13&vfor=1&twpftr=0id=40621&rid=88&vfor=1&twpftr=0 |archive-date=2023-12-27 |access-date=2023-12-27 |website=Cook County Clerk's Office}}}}

{{Election box winning candidate with party link no change|party=Democratic Party (United States)|candidate=Tiffany A. Henyard|votes=1,001|percentage=34.28%}}

{{Election box candidate with party link no change|party=Democratic Party (United States)|candidate=Riley H. Rogers (incumbent)|votes=888|percentage=30.41%}}

{{Election box candidate with party link no change|party=Democratic Party (United States)|candidate=Andrew Holmes |votes=862|percentage=29.52%}}

{{Election box candidate with party link no change|party=Democratic Party (United States)|candidate=Robert Shaw|votes=169|percentage=5.79%}}

{{Election box total no change|votes=2,920|percentage=100}}

{{election box end}}

{{Election box begin no change | title=1984 Illinois's 2nd congressional district Democratic primary}}

{{Election box winning candidate with party link no change

|party = Democratic Party (United States)

|candidate = Gus Savage (incumbent)

|votes = 55,137

|percentage = 45.05

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Glenn V. Dawson

|votes = 26,868

|percentage = 21.95

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Leon Davis

|votes = 15,350

|percentage = 12.54

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Robert Shaw

|votes = 15,316

|percentage = 12.51

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = James C. Taylor

|votes = 9,727

|percentage = 7.95

}}

{{Election box candidate with party link no change

|party = Democratic Party (United States)

|candidate = Others

|votes = 2

|percentage = 0.00

}}

{{Election box total no change

| votes = 72,400

| percentage = 100

}}

{{Election box end}}

{{reflist}}

{{DEFAULTSORT:Shaw, Robert}}

Category:1937 births

Category:2021 deaths

Category:Chicago City Council members

Category:Members of the Cook County Board of Review

Category:African-American people in Illinois politics

Category:Illinois Democrats

Category:Politicians from Chicago

Category:People from South Holland, Illinois

Category:American twins

Category:Politicians from St. Louis

Category:People from Hope, Arkansas

Category:20th-century African-American politicians

Category:21st-century African-American politicians

Category:People from Dolton, Illinois

{{Cook County Board of Review commissioners|state=collapsed}}