![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://sportshub.cbsistatic.com/i/r/2022/01/12/0705ab37-55b8-4dd4-bc43-87934e2d793b/thumbnail/1200x675/b753dc78cfced7ff554eaa4cbc76c23b/lester.png)
Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://cdn.mlbtraderumors.com/files/2021/07/jon-lester-nats.jpg)
Nationals, Cardinals Swap Jon Lester For Lane Thomas - MLB Trade Rumors
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://www.bostonherald.com/wp-content/uploads/migration/2014/06/17/061714soxms03.jpg?w=978)
Longtime Red Sox ace Jon Lester retires after 16 MLB seasons
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://www.usatoday.com/gcdn/-mm-/87f6333defc728af915f188465bf9cd822530c91/c=0-16-2449-1400/local/-/media/USATODAY/USATODAY/2014/12/08/635536572667870017-USP-MLB-Kansas-City-Royals-at-Oakland-Athletics.jpg?width=2449&height=1384&fit=crop&format=pjpg&auto=webp)
Jon Lester, Cubs agree to a six-year, $155 million deal
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://bdc2020.o0bc.com/wp-content/uploads/2015/10/davis_trades3_spts-scaled.jpg)
Former Red Sox teammates Jon Lester and John Lackey put friendship on hold in MLB playoffs
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://images2.minutemediacdn.com/image/upload/c_fill,w_1440,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/https-3A-2F-2Fwhitecleatbeat-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2017-2F07-2F456616522-850x560-7f1156a0d58d1bc5c40cf4f77d0dfaad.jpg)
Former Oakland A's pitcher Jon Lester retires
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://cst.brightspotcdn.com/dims4/default/58608f3/2147483647/strip/true/crop/1023x682+0+2/resize/840x560!/quality/90/?url=https%3A%2F%2Fcdn.vox-cdn.com%2Fthumbor%2FOZD19SmwneCeBGkQffVbGkJ9CPE%3D%2F0x0%3A1023x686%2F1023x686%2Ffilters%3Afocal%28539x126%3A540x127%29%2Fcdn.vox-cdn.com%2Fuploads%2Fchorus_asset%2Ffile%2F19787048%2FScreen_Shot_2020_03_11_at_11.07.10_PM.png)
Jon Lester out of the equation for Cubs' Opening-Day starter - Chicago Sun-Times
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://images2.minutemediacdn.com/image/upload/c_fill,w_1440,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/https-3A-2F-2Fcubbiescrib-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2018-2F08-2F1271262291-850x560-cb3d70dc85607268d29d90bcad3c694a.jpg)
Jon Lester will be the next Cubs player inducted into the Hall of Fame
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://cdn.vox-cdn.com/uploads/chorus_image/image/70378107/452683600.0.jpg)
Jon Lester announces his retirement after long career with Boston Red Sox and Chicago Cubs - Over the Monster
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://cdn.vox-cdn.com/thumbor/Vd9gtKjYZAVKpn4HBuVNCmSRMS4=/0x0:1250x1248/1200x0/filters:focal(0x0:1250x1248):no_upscale()/cdn.vox-cdn.com/uploads/chorus_asset/file/23158271/Screen_Shot_2022_01_10_at_10.21.20_AM.png)
Jon Lester announces his retirement after long career with Boston Red Sox and Chicago Cubs - Over the Monster
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://images2.minutemediacdn.com/image/upload/c_fill,w_1440,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/https-3A-2F-2Fbosoxinjection-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2017-2F07-2F452433252-850x560-e1bec16c75ba750366ab60ee0866ddd1.jpg)
Jon Lester's retirement reminds us Red Sox never should have let him go
![Former Cubs, Red Sox pitcher Jon Lester announces retirement](https://www.usatoday.com/gcdn/media/2022/01/12/USATODAY/usatsports/f616b1a6a0c540a5b122f0ff60f9fbe1.jpg)
Jon Lester, former Cubs, Red Sox pitcher, announces retirement