:Jon Lester

Lester attended Bellarmine Preparatory School in Tacoma, Washington. Playing for the school's baseball team, Lester was a three-time MVP and three-time All-Area selection. In addition, he was named Gatorade State Player of the Year for Washington in 2000.{{cite web|title=Jon Lester – Bio|url=http://www.jockbio.com/Bios/J_Lester/J_Lester_bio.html|access-date=December 11, 2014|work=Jockbio|archive-date=June 2, 2018|archive-url=https://web.archive.org/web/20180602162457/http://www.jockbio.com/Bios/J_Lester/J_Lester_bio.html|url-status=dead}}{{Unreliable source?|date=November 2024}}

The Red Sox selected Lester in the second round, with the 57th overall selection, of the 2002 Major League Baseball draft and gave him the highest signing bonus of any second-rounder that year, $1 million.{{Cite news |url=https://www.newspapers.com/article/the-boston-globe-showing-the-money/149795068/ |title=Showing the money |newspaper=The Boston Globe |page=70 |date=2002-08-16 |access-date=2024-06-21 |via=Newspapers.com}}

Lester quickly moved through the Red Sox organization, posting an 11–7 win–loss record, a league-leading 2.61 earned run average (ERA) and a league-best 163 strikeouts for the Portland Sea Dogs of the Class AA Eastern League in 2005. He was named the Eastern League Pitcher of the Year and Red Sox Minor League Pitcher of the Year and was selected as the left-handed pitcher on the Eastern League's year-end All-Star team and on the year-end Topps Class AA All-Star squad.

Lester was one of the Red Sox' top-rated prospects while in the minors, and other major league teams made efforts to acquire him. The Texas Rangers had demanded Lester be part of the proposed but ultimately rejected deal before the 2004 season for Alex Rodriguez. The Florida Marlins insisted he be included in the trade for Josh Beckett before the 2006 season, but again, the Sox were able to keep Lester.{{cite web|last=Edes|first=Gordon|date=November 22, 2005|title=This Marlin a pretty big fish for Sox to land|url=http://www.boston.com/sports/baseball/redsox/articles/2005/11/22/this_marlin_a_pretty_big_fish_for_sox_to_land/|access-date=October 20, 2011|website=The Boston Globe}}

With a rash of injuries and general ineffectiveness of several Red Sox starters, the team recalled Lester on June 10 to make his major league debut against the Texas Rangers. He put up a 7–2 record and a 4.76 ERA in {{frac|81|1|3}} innings pitched in his rookie year.

On August 27, 2006, Lester was scratched from his scheduled start against the Oakland Athletics due to a sore back. The following day he was placed on the 15-day disabled list, and was sent back to Boston for testing. At the time, Lester's back problems were thought to be the result of a car crash he was involved in earlier in the month. On August 31, it was reported that Lester had been diagnosed with enlarged lymph nodes and was being tested for a variety of ailments, including forms of cancer.{{Cite web|last=Massarotti|first=Tony|date=August 31, 2006|title=Lester tested for cancer -- Sources say rookie has enlarged lymph nodes|url=http://redsox.bostonherald.com/redSox/view.bg?articleid=155293|url-status=live|archive-url=https://web.archive.org/web/20060901185824/http://redsox.bostonherald.com/redSox/view.bg?articleid=155293|archive-date=September 1, 2006|access-date=April 22, 2021|website=Boston Herald}} A few days later, doctors at Massachusetts General Hospital confirmed that Lester had a treatable form of anaplastic large cell lymphoma.{{cite web|author=|date=September 1, 2006|title=Sox: Lester has treatable form of lymphoma|url=http://redsox.bostonherald.com/redSox/view.bg?articleid=155533&srvc=sports|url-status=dead|archive-url=https://web.archive.org/web/20070710220222/http://redsox.bostonherald.com/redSox/view.bg?articleid=155533&srvc=sports|archive-date=July 10, 2007|access-date=September 1, 2006|work=Boston Herald|df=mdy}} Lester underwent off-season chemotherapy treatments at Seattle's Fred Hutchinson Cancer Research Center.{{Cite web|last=Osterweil|first=Neil|date=September 7, 2006|title=Red Sox Rookie Pitcher to Get Chemo for Non-Hodgkin's Lymphoma|url=https://www.medpagetoday.org/hematologyoncology/lymphoma/4065?vpass=1|access-date=April 22, 2021|website=Medpage Today|language=en}} In December 2006, ESPN.com reported that Lester's latest CT Scan showed no signs of the disease, which appeared to be in remission.{{cite news|date=December 5, 2006|title=Doctors pronounce Red Sox hurler Lester cancer-free|work=ESPN|agency=Associated Press|url=https://www.espn.com/mlb/news/story?id=2686799|access-date=December 5, 2006}}

File:Lester Warms.jpg]]

Following the successful treatment of his lymphoma, Lester was able to return to the Red Sox midway through the 2007 season. Lester attended spring training in 2007, and started the season for the class A Greenville Drive. Lester then started for Triple-A Pawtucket Red Sox in late April 2007. In June, Lester was removed from the disabled list, and sent to Pawtucket for further rehab outings.{{cite web|date=June 11, 2007|title=Red Sox option LHP Jon Lester to Pawtucket|url=http://mlb.mlb.com/news/press_releases/press_release.jsp?ymd=20070611&content_id=2019871&vkey=pr_bos&fext=.jsp&c_id=bos|url-status=live|archive-url=https://web.archive.org/web/20071101070903/http://mlb.mlb.com/news/press_releases/press_release.jsp?ymd=20070611&content_id=2019871&vkey=pr_bos&fext=.jsp&c_id=bos|archive-date=November 1, 2007|access-date=June 11, 2007|work=Boston Red Sox}}

Lester made his first 2007 start for the Boston Red Sox on July 23 against the Cleveland Indians at Jacobs Field in Cleveland, pitching six innings, allowing two runs on five hits and struck out six, picking up the win.{{Cite web|date=July 23, 2007|title=Lester beats Indians in return to big leagues|url=https://www.espn.com/mlb/recap/_/gameId/270723105|archive-url=https://web.archive.org/web/20210425042407/https://www.espn.com/mlb/recap/_/gameId/270723105|url-status=dead|archive-date=April 25, 2021|access-date=April 23, 2021|website=ESPN|language=en}} On September 26 against the Oakland Athletics at Fenway Park, Lester gave up what would turn out to be the final career home run by Hall of Fame catcher Mike Piazza. In the 2007 World Series against the Colorado Rockies, Lester won the series-clinching Game 4 for the Red Sox, pitching {{frac|5|2|3}} shutout innings, giving up three hits and three walks while collecting three strikeouts. Lester became the third pitcher in World Series history to win a series clinching game in his first post-season start.{{Cite web|date=October 29, 2007|title=BoSox sweep Rockies to win 2nd World Series in 4 years|url=https://www.espn.com/mlb/recap/_/gameId/271028127|archive-url=https://web.archive.org/web/20210425042405/https://www.espn.com/mlb/recap/_/gameId/271028127|url-status=dead|archive-date=April 25, 2021|access-date=April 23, 2021|website=ESPN|language=en}}

To honor Lester's comeback from lymphoma, the Boston Baseball Writers' Association of America voted him the 2007 Tony Conigliaro Award.{{cite news|last1=Wilbur|first1=Eric|date=November 28, 2007|title=Lester gets the honor|work=The Boston Globe|url=http://www.boston.com/sports/baseball/redsox/extras/extra_bases/2007/11/lester_gets_the.html|access-date=November 28, 2007}}

On May 19, 2008, Lester threw a no-hitter in a 7–0 win against the Kansas City Royals.{{cite web|author=Browne|first=Ian|date=May 19, 2008|title=Lester hurls 18th Red Sox no-no|url=http://boston.redsox.mlb.com/news/gameday_recap.jsp?ymd=20080519&content_id=2731480&vkey=recap&fext=.jsp&c_id=bos|url-status=dead|archive-url=https://web.archive.org/web/20080521065844/http://boston.redsox.mlb.com/news/gameday_recap.jsp?ymd=20080519&content_id=2731480&vkey=recap&fext=.jsp&c_id=bos|archive-date=May 21, 2008|access-date=May 19, 2008|website=Boston Red Sox}} It was the 18th no-hitter in Red Sox history. Lester threw 130 pitches in the game, allowing only two walks and striking out nine batters, and was charged with a throwing error on a pickoff attempt in the second inning. It was the first no-hitter thrown by a Red Sox left-handed pitcher since Mel Parnell in 1956, the first in MLB since teammate Clay Buchholz in September 2007, and the MLB-record fourth no-hitter caught by Jason Varitek. It was also only the second no-hitter ever pitched against the Royals; Nolan Ryan pitched the other in 1973.{{cite web|author=McAdam|first=Sean|date=May 20, 2008|title=Lester traveled hard road to no-hitter|url=https://www.espn.com/mlb/columns/story?id=3404366|access-date=April 20, 2021|website=ESPN}}{{cite web|author=Mullen|first=Maureen|date=May 20, 2008|title=No-hitter not possible without Ellsbury|url=http://mlb.mlb.com/news/article.jsp?ymd=20080519&content_id=2733490&vkey=news_bos&fext=.jsp&c_id=bos|url-status=live|archive-url=https://web.archive.org/web/20080530160126/http://mlb.mlb.com/news/article.jsp?ymd=20080519&content_id=2733490&vkey=news_bos&fext=.jsp&c_id=bos|archive-date=May 30, 2008|access-date=April 23, 2021|website=Boston Red Sox}}

In 2008, Lester went 16–6 with a 3.21 ERA. Along with his no-hitter, he pitched a five-hit shutout in his first start at Yankee Stadium. He was named the AL Pitcher of the Month in July and September. Lester was also a key figure in the Red Sox' victory over the Angels in the American League Divisional Series, pitching 14 innings without allowing an earned run. Lester had the second highest winning percentage of all starting pitchers over the last three years (27–8, .771), and led the Red Sox in innings pitched in 2008 with {{frac|210|1|3}}.{{Cite web|last=Chuck|first=Bill|date=April 2, 2009|title=100 random things about the Red Sox, Rays, and Yankees|url=http://www.boston.com/sports/baseball/redsox/extras/100_random_things_2009/|url-status=live|archive-url=https://web.archive.org/web/20090904044010/http://www.boston.com/sports/baseball/redsox/extras/100_random_things_2009/|archive-date=September 4, 2009|access-date=April 23, 2021|website=The Boston Herald}}

Lester's losses in Games 3 and 7 of the 2008 ALCS were the first losses he had ever had in consecutive starts.{{cite web|title=Jon Lester 2008 Pitching Gamelogs – Baseball-Reference.com|url=https://www.baseball-reference.com/pi/gl.cgi?n1=lestejo01&t=p&year=2008|access-date=October 20, 2008|publisher=Sports Reference}}

Lester also received the 2008 Hutch Award, given to the Major League player who "best exemplifies the fighting spirit and competitive desire" of Hutchinson.{{Cite web|date=October 7, 2008|title=Unknown|url=http://www.ibtimes.com/prnews/20081007/wa-hutch-award-finals.htm|website=International Business Times}} {{Dead link|date=July 2022 |bot=InternetArchiveBot |fix-attempted=yes }}[http://www.sportingnews.com/yourturn/viewtopic.php?t=484840 Real Insight. Real Fans. Real Conversations]{{Dead link|date=December 2022 |bot=InternetArchiveBot |fix-attempted=yes }}. Sporting News. Retrieved November 15, 2011. {{dead link|date=September 2017|bot=InternetArchiveBot|fix-attempted=yes}} {{Dead link|date=July 2022}}

File:Jon Lester on June 29, 2009.jpg

On March 8, Lester agreed to a five-year, $30 million contract extension with a $14 million team option in 2014.{{cite web|last=Passan|first=Jeff|date=March 8, 2009|title=Lester lands five-year extension with Red Sox – MLB – Yahoo! Sports|url=https://sports.yahoo.com/mlb/news?slug=jp-lester1extension030809|url-status=dead|archive-url=https://archive.today/20120715020621/http://sports.yahoo.com/mlb/news?slug=jp-lester1extension030809|archive-date=July 15, 2012|access-date=July 15, 2012|website=Yahoo Sports}}

The season started poorly, with him allowing 11 runs and getting losses in his first two starts.{{cite web|title=Jon Lester 2009 Pitching Gamelogs – Baseball-Reference.com|url=https://www.baseball-reference.com/players/gl.cgi?id=lestejo01&t=p&year=2009|access-date=March 8, 2015|publisher=Sports Reference}} This was the first time he lost in consecutive regular season starts. He began to pitch very well in late May, going 12–3 with a 2.31 ERA in his final 22 starts.

On June 6, Lester made his bid for a second no-hitter against the AL West-leading Texas Rangers at Fenway. He pitched 6{{fraction|1|3}} perfect innings, striking out 10 batters on 61 pitches through the first six innings. Michael Young hit a one-out double to left center field in the seventh inning to break up the no-hitter, but Lester pitched a complete game, striking out a total of 11 batters, giving him 23 strikeouts in two starts (he had a career-best 12 strikeouts his previous start).{{Cite web|date=June 6, 2009|title=Lester retires first 19 batters, Ortiz homers to propel Red Sox|url=https://www.espn.com/mlb/recap/_/gameId/290606102|archive-url=https://web.archive.org/web/20210425043913/https://www.espn.com/mlb/recap/_/gameId/290606102|url-status=dead|archive-date=April 25, 2021|access-date=April 24, 2021|website=ESPN|language=en}} On August 14, Lester struck out ten batters for the sixth time in the 2009 season, the most times ever by a Red Sox left-handed pitcher. He had never done it before that season. Lester started 32 games in 2009, going 15–8 with a 3.41 ERA.

Lester started Game 1 of the 2009 ALDS against the Los Angeles Angels of Anaheim, but the Red Sox lost the game 5–0 and would eventually be swept in the series.{{cite web|title=Jon Lester Postseason Pitching Gamelog – Baseball-Reference.com|url=https://www.baseball-reference.com/players/gl.cgi?id=lestejo01&t=p&year=0&post=1|access-date=March 8, 2015|publisher=Sports Reference}}

In 2010, Lester won his final start in April, then won five of the six games he started in May. Lester went 5–0 with a 1.84 ERA and 45 strikeouts and was named the American League Pitcher of the Month, winning the award for the third time.

On June 16, he got his 50th career win, against the Arizona Diamondbacks. Lester was selected to the American League All-Star team on July 1, this was his first selection. At the time of the break he was 11–3 with a 2.78 ERA and 124 strikeouts. He pitched the sixth inning for the AL allowing no baserunners.

On July 25, Lester took a perfect game into the sixth inning against the Seattle Mariners, but lost it in that inning due to an error made by Eric Patterson. A home run by Michael Saunders broke up the no-hit bid, and the Red Sox eventually lost the game.{{Cite web|date=July 25, 2010|title=Mariners pull out split with Red Sox after three-run rally in 8th|url=https://www.espn.com/mlb/recap/_/gameId/300725112|archive-url=https://web.archive.org/web/20210425043914/https://www.espn.com/mlb/recap/_/gameId/300725112|url-status=dead|archive-date=April 25, 2021|access-date=April 25, 2021|website=ESPN|language=en}} The loss was the second of four losses in a row Lester took after the All-Star break. He would eventually turn it around throwing six shutout innings against the Yankees and then eight shutout innings, despite feeling sick, against the Rangers. Lester finished the season strong and developed an excellent pickoff move, but fell just short of 20 wins.

Lester finished the season T-4th in wins (19) and in fourth place in strikeouts (225) in the Majors (AL and NL combined) in 2010. He finished 25th in the Major Leagues with a 3.25 ERA in an above average year for pitchers. Lester finished fourth in voting for the 2010 AL Cy Young Award as well.

In 2011, Lester was the opening day starter for the Red Sox, on the road against Texas. He had a solid season, leading Boston's rotation in wins for the second year in a row and strikeouts for the third year in a row. He was named to the American League All-Star team, replacing Félix Hernández, but did not pitch due to a lat injury.

Lester struggled along with the rest of the team, losing his last three decisions, including giving up eight runs in a start against the New York Yankees. He pitched the season finale against the Baltimore Orioles, pitching six innings and giving up just two runs. The bullpen was unable to hold onto the lead, and the Red Sox were eliminated. Lester finished the season 15–9 with a 3.41 ERA. He finished in the top 20 in strikeouts (11th), wins (10th) and ERA (17th).

In the end of the 2011 season, Lester, Josh Beckett, and John Lackey were at the center of a controversy about players drinking alcohol during games. Many people{{Who?|date=September 2022}} hypothesized that this was part of the reason why the Red Sox went 7–20 in September and were eliminated on the last day of the season. Lester later admitted that he and teammates occasionally drank during off-days.{{cite web|last=Browne|first=Ian|date=October 17, 2011|title=Lester: We did drink in clubhouse during games|url=http://boston.redsox.mlb.com/news/article.jsp?ymd=20111017&content_id=25692288&vkey=news_bos&c_id=bos|url-status=dead|archive-url=https://web.archive.org/web/20111020121345/http://boston.redsox.mlb.com/news/article.jsp?ymd=20111017&content_id=25692288&vkey=news_bos&c_id=bos|archive-date=October 20, 2011|access-date=October 20, 2011|df=mdy-all}}

Image:LestersNo-No.jpg following Jon Lester's no-hitter, May 19, 2008]]

In 2012, Lester was again the opening day starter for the Red Sox. Lester had a disappointing season, posting a 9–14 record, a sub-par 4.82 ERA, and a .273 batting average against.

On May 10, 2013, Lester threw a complete game one-hitter, with no walks, against the Toronto Blue Jays, facing just 28 batters.{{Cite web|last=Abraham|first=Peter|date=May 10, 2013|title=Jon Lester nearly perfect in Red Sox' 5-0 win over Blue Jays|url=https://www.boston.com/sports/boston-red-sox/2013/05/10/jon-lester-nearly-perfect-in-red-sox-5-0-win-over-blue-jays|access-date=April 24, 2021|website=Boston Globe|language=en-US}}

On October 3, 2013, Lester was named as the starting pitcher for Game 1 of the 2013 ALDS against the Tampa Bay Rays in Boston's first return to the postseason since 2009.{{Cite web|last=Lee|first=Tony|date=October 2, 2013|title=Jon Lester to start ALDS Game 1|url=https://www.espn.com/mlb/story/_/id/9760876/2013-mlb-playoffs-jon-lester-boston-red-sox-start-game-1-alds|access-date=April 24, 2021|website=ESPN|language=en}} The following day, Lester pitched {{frac|7|2|3}} innings with three walks and striking out seven, and the Red Sox won 12–2 (and later went on to win the series 3–1).{{Cite web|date=October 4, 2013|title=Red Sox take advantage of Rays miscues to cruise in Game 1|url=https://www.espn.com/mlb/recap/_/gameId/331004102|archive-url=https://web.archive.org/web/20210425042406/https://www.espn.com/mlb/recap/_/gameId/331004102|url-status=dead|archive-date=April 25, 2021|access-date=April 24, 2021|website=ESPN|language=en}} Lester also tied Josh Beckett's Red Sox postseason record of striking out the first four batters to begin the game. Lester started Game 1 of the 2013 ALCS against the Detroit Tigers on October 12, 2013.{{Cite web|date=October 13, 2013|title=Tigers lose no-no with one out in 9th, edge Red Sox in ALCS Game 1|url=https://www.espn.com/mlb/recap/_/gameId/331012102|archive-url=https://web.archive.org/web/20210425042406/https://www.espn.com/mlb/recap/_/gameId/331012102|url-status=dead|archive-date=April 25, 2021|access-date=April 24, 2021|website=ESPN|language=en}} He pitched {{frac|6|1|3}} innings with four strikeouts and allowed one run, but was outmatched by a one-hit game put together by the Tigers' pitching staff led by starter Aníbal Sánchez. At Comerica Park on October 17, 2013, Lester again faced Sanchez in Game 5. The Red Sox won 4–3 with Lester pitching five innings and showing spectacular defensive skills in the fifth inning throwing out former teammate Jose Iglesias with a glove flip to first base on a bunt attempt.{{Cite web|date=October 17, 2013|title=Red Sox move one win away from World Series|url=https://www.espn.com/mlb/recap/_/gameId/331017106|archive-url=https://web.archive.org/web/20210425042408/https://www.espn.com/mlb/recap/_/gameId/331017106|url-status=dead|archive-date=April 25, 2021|access-date=April 24, 2021|website=ESPN|language=en}}

After the Red Sox victory in the ALCS, Lester was selected to start Game 1 of the 2013 World Series against the St. Louis Cardinals. Lester pitched to an 8–1 victory over St. Louis starter Adam Wainwright.{{Cite web|date=October 23, 2013|title=Red Sox cruise past sloppy Cardinals in Game 1 of World Series|url=https://www.espn.com/mlb/recap?gameId=331023102|archive-url=https://web.archive.org/web/20181118144856/http://www.espn.com/mlb/recap?gameId=331023102|url-status=dead|archive-date=November 18, 2018|access-date=April 24, 2021|website=ESPN}} Lester then went on to a Game 5 win again over Wainwright giving the Red Sox a series lead of 3–2.{{Cite web|date=October 28, 2014|title=Jon Lester's gem in Game 5 puts Red Sox one win from title|url=https://www.espn.com/mlb/recap/_/gameId/331028124|archive-url=https://web.archive.org/web/20210425042410/https://www.espn.com/mlb/recap/_/gameId/331028124|url-status=dead|archive-date=April 25, 2021|access-date=April 24, 2021|website=ESPN|language=en}} The Red Sox won the series in six games.

On May 3, 2014, Lester pitched eight one-hit innings against the Oakland Athletics, where he had a career-high 15 strikeouts.{{Cite magazine|last=Tayler|first=Jon|date=May 3, 2014|title=Jon Lester sets career high in strikeouts as Red Sox top Athletics|url=https://www.si.com/mlb/2014/05/03/jon-lester-15-strikeouts-red-sox-athletics|access-date=April 24, 2021|magazine=Sports Illustrated|language=en-us}} It was the most by a Red Sox pitcher since Josh Beckett in 2010.

He was elected to his third All-Star Game in July 2014 after posting a 2.73 ERA over his first 18 starts of the season.{{cite web|last=Penney|first=Sean|date=July 7, 2014|title=Jon Lester Makes the All-Star Team|url=http://www.sportsmedia101.com/bostonredsox/2014/07/07/jon-lester-makes-the-all-star-team/|url-status=dead|archive-url=https://web.archive.org/web/20140714213553/http://www.sportsmedia101.com/bostonredsox/2014/07/07/jon-lester-makes-the-all-star-team/|archive-date=July 14, 2014|access-date=July 8, 2014|website=Sports Media 101|df=mdy-all}}

On July 31, 2014, Lester and Jonny Gomes were traded to the Oakland Athletics for Yoenis Céspedes and a competitive round 2015 draft pick. The move reunited Lester with former teammates Jed Lowrie, Coco Crisp, Brandon Moss and Josh Reddick.{{cite web|last=Nightengale|first=Bob|date=July 31, 2014|title=A's acquire Jon Lester, send Cespedes to Boston|url=https://www.usatoday.com/story/sports/mlb/2014/07/31/jon-lester-trade-red-sox-oakland-athletics/13401893/|access-date=July 31, 2014|website=USA Today}} He won his debut start against the Kansas City Royals on August 2.{{cite web|last1=Lee|first1=Jane|date=August 3, 2014|title=New guys shine, bats come alive in Lester's debut|url=http://mlb.mlb.com/mlb/gameday/index.jsp?gid=2014_08_02_kcamlb_oakmlb_1&mode=wrap&partnerId=LR_wrap#gid=2014_08_02_kcamlb_oakmlb_1&mode=recap&c_id=oak|access-date=August 3, 2014|work=MLB.com}} He had a 6–4 record and a 2.35 ERA, while pitching for the A's.

Lester was the starting pitcher for the A's in the Wild Card game, against the Kansas City Royals. He left the game after pitched {{frac|7|1|3}} innings with the Athletics leading 7–4. Lester, however, received a no decision, as the bullpen blew the lead, and the Royals made a dramatic comeback to win the game in 12 innings.{{Cite web|last=Mastrodonato|first=Jason|date=October 1, 2014|title=Jon Lester throws worst playoff start of his career for Oakland A's -- Was he missing the fire?|url=https://www.masslive.com/redsox/2014/10/jon_lester_throws_worst_postse.html|access-date=April 24, 2021|website=The Republican|language=en}}

Lester had a 16–11 record with a 2.46 ERA and finished fourth in the AL Cy Young voting.{{Cite web|title=2014 Awards Voting|url=https://www.baseball-reference.com/awards/awards_2014.shtml|access-date=April 24, 2021|website=Baseball-Reference|language=en}}

In December 2014, Lester agreed to a six-year, $155 million deal with the Chicago Cubs with a vesting option for a seventh year at $15 million.{{cite web|last=Muskat|first=Carrie|date=December 10, 2014|title=Free agent Lester agrees to deal with Cubs|url=http://m.cubs.mlb.com/news/article/103652288/free-agent-jon-lester-agrees-to-deal-with-chicago-cubs|url-status=dead|archive-url=https://web.archive.org/web/20141214234554/http://m.cubs.mlb.com/news/article/103652288/free-agent-jon-lester-agrees-to-deal-with-chicago-cubs|archive-date=December 14, 2014|access-date=January 20, 2015|work=Chicago Cubs}}{{cite web|date=December 10, 2014|title=Jon Lester chooses Chicago Cubs|url=https://www.espn.com/chicago/mlb/story/_/id/12008073/jon-lester-sign-chicago-cubs|access-date=January 20, 2015|work=ESPN}}

Lester made his first start for the Cubs during opening night on April 5, 2015 against the St. Louis Cardinals. He pitched 4.1 innings allowing 3 runs as the Cubs were shut out by the Cardinals 3–0.{{cite web|last1=Cohen|first1=Jay|date=April 6, 2015|title=Lester's Cubs debut doesn't go well.|url=https://www.bostonglobe.com/sports/2015/04/05/jon-lester-struggles-cubs-fall-cardinals-opener/tL2dIBPPeCHiuMiJFtOKBL/story.html|access-date=April 7, 2015|website=Boston Globe|publisher=Associated Press}} He finished the month of April with a record of 0–2 and an ERA of 6.23 in 21.2 innings pitched with 24 strikeouts and five base-on balls.{{Cite web|title=Jon Lester Game by Game Stats and Performance|url=https://www.espn.com/mlb/player/gamelog/_/id/28487/jon-lester|access-date=April 24, 2021|website=ESPN|language=en}}

On May 27, 2015, matchup with the Washington Nationals, Lester hit a fly ball to deep center field that nearly eluded Denard Span. Span caught the fly ball to end the inning, bringing Lester to a record-setting 0-for-58 to start his career.{{cite news|last=Snyder|first=Matt|date=May 27, 2015|title=Jon Lester sets dubious record by starting career 0-for-58|agency=CBS Sports|url=http://www.cbssports.com/mlb/eye-on-baseball/25197729/jon-lester-sets-dubious-record-by-starting-career-0-for-58|access-date=May 27, 2015|archive-url=https://web.archive.org/web/20160304111719/http://www.cbssports.com/mlb/eye-on-baseball/25197729/jon-lester-sets-dubious-record-by-starting-career-0-for-58|url-status=dead|archive-date=March 4, 2016}} On July 6, 2015, Lester recorded his first career major league hit against John Lackey of the St. Louis Cardinals after starting his career 0-for-66 as a hitter.{{cite web|last1=Muskat|first1=Carrie|date=July 7, 2015|title=At long last, a hit for Lester|url=https://www.mlb.com/news/jon-lester-records-first-career-hit/c-135106696|access-date=June 29, 2020|website=MLB.com}}

Lester posted an 11–13 record, logging 205 innings pitched with an ERA of 3.34 in his first year with the Chicago Cubs. He led the major leagues in stolen bases allowed, with 44.{{Cite web|title=2015 Major League Baseball Baserunning/Situ|url=https://www.baseball-reference.com/leagues/MLB/2015-basesituation-pitching.shtml|access-date=April 24, 2021|website=Baseball-Reference}}

On October 9, he was the losing pitcher in Game 1 of the NLDS versus the St. Louis Cardinals.{{Cite web|last=Yellon|first=Al|date=October 10, 2015|title=Cardinals 4, Cubs 0: Lackey Outpitches Lester|url=https://www.bleedcubbieblue.com/2015/10/10/9492447/nlds-game-1-recap-cardinals-cubs-john-lackey-jon-lester-mlb-scores|access-date=April 24, 2021|website=Bleed Cubbie Blue|publisher=SB Nation|language=en}} On October 17, he took another loss in Game 1 of the NLCS versus the New York Mets.{{Cite web|last=Kane|first=Colleen|date=October 17, 2015|title=Mets defeat Cubs 4-2 in Game 1 of NLCS|url=https://www.chicagotribune.com/sports/cubs/ct-gameday-cubs-mets-spt-1018-20151017-story.html|access-date=April 24, 2021|website=Chicago Tribune}}

On July 31, 2016, against the Seattle Mariners, Lester came off the bench in the 12th inning and laid a bunt down to score the winning run. On a 2–2 pitch with one out and Jason Heyward on 3rd, Lester capped off a wild comeback for the Cubs, who rallied back from a 6–0 deficit in the third inning.{{Cite web|last=Cohen|first=Jay|date=July 31, 2016|title=Lester squeezes in deciding run, Cubs beat Mariners in 12|url=https://www.dailyherald.com/article/20160731/sports/307319900|access-date=April 24, 2021|website=Daily Herald|language=en-US}}

In 2016, Lester finished second in the NL with 19 wins, matching his career high. He was also second in ERA (2.44). He led all major league pitchers in left on base percentage, stranding 84.9% of base runners.{{Cite web|title=Major League Leaderboards » 2016 » Pitchers » Dashboard | FanGraphs Baseball|url=https://www.fangraphs.com/leaders.aspx?pos=all&stats=pit&lg=all&qual=y&type=8&season=2016&month=0&season1=2016&ind=0&team=0&rost=0&age=0&filter=&players=0&sort=13,d|access-date=April 20, 2021|website=Fangraphs}}

Lester started Game 1 of the 2016 NLDS against the San Francisco Giants. He earned the win after tossing eight scoreless innings.{{Cite web |date=October 7, 2016 |title=Jon Lester, Javier Baez help Cubs eke past Giants in NLDS opener |url=https://www.espn.com/mlb/recap/_/gameId/361007116 |access-date=April 24, 2021 |website=ESPN|agency=Associated Press |language=en}} The Cubs would go on to win the series in four games.

File:Jon Lester Game 7 2016 World Series.jpg]]

Lester also started Game 1 of the 2016 National League Championship Series against the Los Angeles Dodgers, he pitched six innings and allowed just one run and had a no-decision.{{Cite magazine|last=Verducci|first=Tom|date=October 16, 2016|title=Managerial madness leads to Cubs win in NLCS Game 1|url=https://www.si.com/mlb/2016/10/16/nlcs-game-1-cubs-dodgers-miguel-montero|access-date=April 24, 2021|magazine=Sports Illustrated|language=en-us}} He also started Game 5 of the series and pitched seven innings of one run ball, earning his third win of the postseason.{{Cite magazine|last=Ducey|first=Kenny|date=October 21, 2016|title=Cubs top Dodgers in Game 5, take control of NLCS|url=https://www.si.com/mlb/2016/10/21/cubs-dodgers-nlcs-game-5-recap|access-date=April 24, 2021|magazine=Sports Illustrated|language=en-us}} The Cubs would go on and win the series in six games. Lester was named Co-MVP of the 2016 NLCS along with Javier Báez.{{Cite web|last=Langosch|first=Jenifer|date=October 22, 2016|title=Lester, Baez share MVP honors|url=https://www.mlb.com/news/jon-lester-javier-baez-named-nlcs-mvps-c206897172|access-date=April 24, 2021|website=MLB.com|language=en}} Lester's performance helped propel the Cubs to the World Series for the first time since 1945.

Lester was named the Game 1 starter of the 2016 World Series against the Cleveland Indians, where he took the loss after throwing 5.2 innings and allowing three runs.{{Cite web|last1=Bastian|first1=Jordan|last2=Muskat|first2=Carrie|date=October 25, 2016|title=Corey, Corey, hallelujah: Tribe wins big G1|url=https://www.mlb.com/news/indians-shut-out-cubs-in-world-series-game-1-c207151992|access-date=April 24, 2021|website=MLB.com|language=en}} Lester also started Game 5, allowing just two runs in six innings, leading to a 3–2 Cubs victory to extend the series.{{Cite web|last=Martin|first=Jill|date=October 31, 2016|title=Chicago Cubs stay alive, win World Series Game 5|url=https://edition.cnn.com/2016/10/30/sport/world-series-game-5-cleveland-indians-chicago-cubs/index.html|access-date=April 24, 2021|website=CNN|language=en}} Lester pitched in relief in Game 7, which the Cubs won, to win their first championship in 108 years.{{cite web|last1=Bastian|first1=Jordan|last2=Muskat|first2=Carrie|date=November 3, 2016|title=Chicago Cubs win 2016 World Series|url=https://www.mlb.com/news/chicago-cubs-win-2016-world-series-c207938228|access-date=November 3, 2016|work=MLB.com|archive-date=November 30, 2017|archive-url=https://web.archive.org/web/20171130223630/http://m.mlb.com/news/article/207938228/chicago-cubs-win-2016-world-series/|url-status=live}} Lester was voted the Babe Ruth award as postseason MVP by the New York chapter of the Baseball Writers' Association of America.{{Cite web|date=November 4, 2016|title=Lester voted postseason MVP by New York baseball writers|url=https://www.usatoday.com/story/sports/mlb/2016/11/04/lester-voted-postseason-mvp-by-new-york-baseball-writers/93298128/|access-date=October 3, 2023|website=USA Today|language=en}}

On August 1, Lester recorded his 2,000th career strikeout, and also hit his first career home run.{{cite web|last1=Muskat|first1=Carrie|date=August 1, 2017|title=Jon Lester hits first homer, racks up 2,000th K|url=https://www.mlb.com/news/jon-lester-homers-collects-strikeout-2-000-c245852464|access-date=August 1, 2017|website=MLB.com|publisher=|archive-date=August 2, 2017|archive-url=https://web.archive.org/web/20170802164440/http://m.mlb.com/news/article/245852464/jon-lester-homers-collects-strikeout-2000/?topicId=27118122|url-status=live}} On August 18, Lester was placed on the 10-day disabled list due to left shoulder fatigue.{{cite web|last1=Muskat|first1=Carrie|date=August 18, 2017|title=Cubs place Jon Lester on DL with shoulder fatigue|url=https://www.mlb.com/news/cubs-place-jon-lester-on-disabled-list-c249184536|access-date=August 18, 2017|website=MLB.com|publisher=|archive-date=August 19, 2017|archive-url=https://web.archive.org/web/20170819015809/http://m.mlb.com/news/article/249184536/cubs-place-jon-lester-on-disabled-list/?topicId=27118122|url-status=live}}

File:Jon Lester (47664047441) (cropped).jpg]]

During spring training, Lester was announced as the Opening Day starter for the Cubs.{{cite web|last1=Muskat|first1=Carrie|date=February 27, 2018|title=Lester gets Cubs' Opening Day assignment|url=https://www.mlb.com/news/jon-lester-to-start-opening-day-for-cubs/c-267372390|access-date=May 9, 2018|website=MLB.com|publisher=Major League Baseball}} On July 1, 2018, Lester hit his 2nd career home run, a three-run shot, off of Lance Lynn in an 11–10 win over the Minnesota Twins.{{Cite web|last=Berardino|first=Mike|date=July 1, 2018|title=Lance Lynn chased as Twins fall 10 games under .500 for first time since 2016|url=https://www.twincities.com/2018/07/01/jon-lester-beats-twins-with-arm-and-bat-in-11-10-cubs-win/|access-date=April 24, 2021|website=St. Paul Pioneer Press|language=en-US}}

Owning an 11–2 record with a 2.25 ERA, Lester was named to the 2018 MLB All-Star Game, although he was not able to participate and was replaced by Zack Greinke due to the fact that he had pitched on the Sunday before the game.{{cite web|last=Eurich|first=Matt|date=July 8, 2018|title=Javy Baez, Willson Contreras and Jon Lester named All-Stars|url=https://247sports.com/Article/Javy-Baez-Willson-Contreras-and-Jon-Lester-named-All-Stars-for-Chicago-Cubs-119662579/|access-date=July 8, 2018|website=247 Sports}} For the season he was 18–6 with a 3.32 ERA.

Lester was named the Opening Day starter for the third consecutive year and the eighth time in his career. He earned the win in a 12–4 Cubs victory against the Texas Rangers. On August 6, 2019, he called himself the "weakest link" in the Cubs rotation after giving up a career high 11 runs in a 11–4 loss to the Oakland Athletics.{{Cite web|date=August 6, 2019|title=Lester gives up 11 runs, calls himself 'weakest link' in Cubs rotation|url=https://www.nbcsports.com/chicago/cubs/jon-lester-gives-career-high-11-runs-calls-himself-weakest-link-cubs-rotation|access-date=August 7, 2019|website=NBC Sports Chicago}}

Lester endured the worst season of his Cubs career in 2020, finishing with a 3–3 record and 5.16 ERA with 42 strikeouts in 61.0 innings pitched.{{Cite web|last=Delucchi|first=Marc|date=November 24, 2020|title=Report: SF Giants Showing Interest In Jon Lester|url=https://aroundthefoghorn.com/2020/11/24/sf-giants-jon-lester-chicago-cubs/|access-date=April 25, 2021|website=Around the Foghorn|language=en-US}} He became a free agent after the season.

File:Washington Nationals starting pitcher Jon Lester (34) from Tampa Bay Rays vs Washington Nationals at Nationals Park. June 30, 2021 - Washington ,DC, (All-Pro Reels Photography) (51295526481) (cropped).jpg

On January 27, 2021, Lester signed a one-year, $5 million contract with the Washington Nationals for the 2021 season.{{Cite web|last=Blum|first=Ronald|date=January 27, 2021|title=Lefty Jon Lester finalizes $5M, 1-year deal with Nationals|url=https://sports.yahoo.com/lefty-jon-lester-finalizes-5m-205700278.html|access-date=April 25, 2021|website=Yahoo Sports|language=en-US|archive-date=February 1, 2021|archive-url=https://web.archive.org/web/20210201191230/https://sports.yahoo.com/lefty-jon-lester-finalizes-5m-205700278.html|url-status=dead}} He was the first player to wear 34 on the team since Bryce Harper left in 2019.{{Cite news |url=https://www.newspapers.com/article/tampa-bay-times-lester-debuts-2-weeks-af/149795306/ |title=Lester debuts 2 weeks after gland removal |newspaper=Tampa Bay Times |page=C5 |date=2021-03-19 |access-date=2024-06-21 |via=Newspapers.com}}

On July 30, 2021, Lester was traded to the St. Louis Cardinals in exchange for Lane Thomas.{{cite web|url=https://www.mlb.com/cardinals/news/jon-lester-trade-2021|title=Cards add veteran arms Lester, Happ|work=MLB.com|date=July 30, 2021|first=Zachary|last=Silver}} He earned his 200th career victory on September 20, 2021, against the Milwaukee Brewers, making him one of only three active pitchers (at that time) to achieve that mark. Lester made 12 appearances for St. Louis, going 4–1 with a 4.36 ERA and 40 strikeouts. Lester became a free agent following the season.

On January 12, 2022, Lester announced his retirement. At the time of his retirement, he was the last active player from the 2007 Boston Red Sox's World Series-winning roster.{{cite news |last1=Rogers |first1=Jesse |title=Jon Lester announces retirement after 16 seasons, three World Series titles |url=https://www.espn.com/mlb/story/_/id/33048654/jon-lester-announces-retirement-16-seasons-three-world-series-titles |access-date=January 13, 2022 |work=ESPN.com |date=January 12, 2022}}

Lester has had well-documented problems throwing the ball to first base, normally a routine task for a professional pitcher. This is a phenomenon known as the yips. In 2015, it was noted that Lester had not attempted a pickoff for more than one year, before creating wild throws in his latest attempts.{{Cite web|last=Gaines|first=Cork|date=April 14, 2015|title=The Cubs' $155 million ace Jon Lester can't throw the ball to first base, and it's getting ugly|url=https://www.businessinsider.com/jon-lester-first-base-throws-yips-2015-4?r=DE&IR=T|access-date=June 6, 2020|website=Business Insider}} In 2018, it was reported that Lester tried to get around his problems by bouncing his throws to first base.{{Cite web|last=Sullivan|first=Paul|date=March 4, 2018|title=Jon Lester tackles throwing to bases one bounce at a time|url=https://www.chicagotribune.com/sports/cubs/ct-spt-cubs-jon-lester-throwing-problems-20180304-story.html|access-date=June 6, 2020|website=Chicago Tribune}}

File:Jon Lester and his boys watch the 2016 T-Mobile -HRDerby (27957925714).jpg]]

As of June 11, 2019, Forbes estimated that Lester's annual income was $25.3 million.{{cite web |url=https://www.forbes.com/profile/jon-lester/ |title=Jon Lester |work=Forbes |year=2015 |access-date=April 28, 2016 }}

Lester grew up in Puyallup, Washington and attended All Saints School. He later attended Bellarmine Preparatory School where he was a three-time MVP and three-time All-Area selection. On January 9, 2009, Lester married Farrah Stone Johnson,Lowitt, Bruce (June 11, 2012). [http://mlb.mlb.com/content/printer_friendly/mlbpa/y2012/m06/d11/c33134074.jsp "Birth of son inspires Jon Lester"], MLBPlayers.com. Retrieved June 11, 2012. who he met in 2007 while making rehab starts in single-A Greenville.{{cite web|date=July 11, 2008|title=Jon Lester Off The Marriage Market|url=http://wbztv.com/sports/jon.lester.engaged.2.768683.html|url-status=dead|archive-url=https://web.archive.org/web/20090506081315/http://wbztv.com/sports/jon.lester.engaged.2.768683.html|archive-date=May 6, 2009|access-date=May 6, 2009|work=WBZ-TV}} Together, they have two sons{{Cite web |date=March 8, 2016 |title=Get a look inside Cubs pitcher Jon Lester's luxury home |url=https://www.chicagotribune.com/2016/03/08/get-a-look-inside-cubs-pitcher-jon-lesters-luxury-home/ |access-date=2024-06-27 |website=Chicago Tribune}} and one daughter.{{cite web|last=Muskat|first=Carrie|date=March 5, 2017|title=Cubs' Jon Lester names daughter Cy Elizabeth|url=https://www.mlb.com/news/cubs-jon-lester-names-daughter-cy-elizabeth/c-218086818|access-date=March 5, 2017|website=MLB.com}} During the season, they resided in the Graceland West neighborhood of Chicago in a $3.8 million home, but sold it in 2021 after Lester left the Cubs.{{Cite web|first=Jordan|last= Cohn|url=https://www.audacy.com/sports/mlb/see-inside-the-huge-usd6-million-mansion-listed-by-jon-lester|title = See inside the beautiful $6 million mansion listed by pitcher Jon Lester| date = April 21, 2021 | publisher=Audacy |archiveurl=https://web.archive.org/web/20220125202052/https://www.audacy.com/sports/mlb/see-inside-the-huge-usd6-million-mansion-listed-by-jon-lester|archive-date=January 25, 2022}} They reside in the Buckhead neighborhood of Atlanta during the offseason, and Lester owns 1,500 acres in the southwest part of Georgia.{{Cite web|first=Jill |last= Becker| url=https://simplybuckhead.com/15-minutes-with-jon-lester/|title=15 Minutes with Jon Lester| date=March 7, 2019| publisher=Simply Buckhead}}

Lester and his wife Farrah established NVRQT, short for "Never Quit", in 2011 to support children with cancer and researchers working towards a cure.{{cite web|date=May 11, 2012|title=Red Sox' Lester Launches 'NVRQT' To Fight Children's Cancer|url=http://boston.cbslocal.com/2012/05/11/red-sox-lester-launches-nvrqt-to-fight-childrens-cancer/|access-date=July 18, 2013|publisher=CBS Boston}}{{cite web|title=What is NVRQT?|url=https://www.nvrqt.org/|url-status=dead|archive-url=https://web.archive.org/web/20130616133344/https://www.nvrqt.org/|archive-date=June 16, 2013|access-date=July 18, 2013|publisher=NVRQT|df=mdy}}

In his free time, Lester is an avid hunter and a wine aficionado. During the 2015 offseason, in an attempt to woo him, the Chicago Cubs sent Lester fine wines and camouflage Cubs shirts.{{cite web|url=http://www.chicagotribune.com/sports/baseball/cubs/ct-cubs-jon-lester-make-history-spt-1007-20161006-story.html|title=Jon Lester's moment to make history with the Cubs has arrived|last=Sullivan|first=Paul|date=October 6, 2016|publisher=Chicago Tribune|access-date=November 2, 2016}}{{cite book|last1=Passan|first1=Jeff|url=https://books.google.com/books?id=_A8oCgAAQBAJ|title=The Arm: Inside the Billion-Dollar Mystery of the Most Valuable Commodity in Sports|date=April 5, 2016|publisher=HarperCollins|isbn=9780062400383|language=en|access-date=January 14, 2018}}

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