![Chicago Cubs will benefit from a comfortable Jon Lester](https://www.usatoday.com/gcdn/presto/2020/11/01/USAT/22397026-e737-48d6-8dbd-09890b943be7-USATSI_14988048.jpg?width=1200&disable=upscale&format=pjpg&auto=webp)
Cubs free agent Jon Lester buying beers for fans at Chicago bars
![Chicago Cubs will benefit from a comfortable Jon Lester](https://static01.nyt.com/images/2017/06/18/sports/18KEPNER1/18KEPNER1-articleLarge.jpg?quality=75&auto=webp&disable=upscale)
300 Wins? Today, Try 200 Innings - The New York Times
![Chicago Cubs will benefit from a comfortable Jon Lester](https://www.cincinnati.com/gcdn/-mm-/3a9ad3204d47824f671db09782ed1f193ed63c1a/c=233-0-3037-3738/local/-/media/2016/04/23/Cincinnati/Cincinnati/635970408815918552-USATSI-9265803.jpg?width=660&height=880&fit=crop&format=pjpg&auto=webp)
BAR: Being bad helped Cubs be good
![Chicago Cubs will benefit from a comfortable Jon Lester](https://bloximages.chicago2.vip.townnews.com/eagletribune.com/content/tncms/assets/v3/editorial/2/3f/23f0564a-fa6c-11ec-bebe-ff6ee2b6ca76/62c0eb6f92ca6.image.jpg?resize=1200%2C900)
Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports
![Chicago Cubs will benefit from a comfortable Jon Lester](https://bloximages.chicago2.vip.townnews.com/nwitimes.com/content/tncms/assets/v3/editorial/8/b8/8b84536c-ea11-5d5b-a56c-a54301ef4141/5f55a17eefda1.image.jpg?resize=1200%2C800)
Jon Lester struggles again as Cubs fall to Cardinals
![Chicago Cubs will benefit from a comfortable Jon Lester](https://www.chicagotribune.com/resizer/DiJp1o_qaMN4LOnIxueHNCSRLz8=/1200x630/filters:format(jpg):quality(70)/www.trbimg.com/img-577da7c4/turbine/ct-cubs-lester-event-chicago-inc-spt-0707-20160706)
Cubs' Jon Lester goes country for good cause
![Chicago Cubs will benefit from a comfortable Jon Lester](https://kubrick.htvapps.com/htv-prod/ibmig/cms/image/wcvb/22050592-22050592.jpg?crop=1.00xw:0.758xh;0,0&resize=900:*)
Former Red Sox pitcher, World Series champion Jon Lester retiring, report says
![Chicago Cubs will benefit from a comfortable Jon Lester](https://www.usatoday.com/gcdn/presto/2019/03/26/USAT/f155672f-d0b6-49ce-a199-c625c4ca2b27-USATSI_12338769.jpg?crop=1460,1933,x744,y0)
Jon Lester: Cubs veteran has no hard feelings towards Red Sox
![Chicago Cubs will benefit from a comfortable Jon Lester](https://images2.minutemediacdn.com/image/upload/c_fill,w_1440,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/f0cf488abcd763cfcba3118a1e3fcd72b2618252f977d02cee09c1f8b8a04520.jpg)
Boston Red Sox Rumors: Time for Jon Lester to come home
![Chicago Cubs will benefit from a comfortable Jon Lester](https://www.dailynews.com/wp-content/uploads/migration/2016/201610/SPORTS_161029923_EP_-1_TTHGEEMUHNFO.jpg?w=620)
Jon Lester has delivered for Cubs this postseason – Daily News
![Chicago Cubs will benefit from a comfortable Jon Lester](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-2Ftomahawktake-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2017-2F07-2F1277027105-850x560-1f05218c0912cf78f074f2e592b2844f.jpg)
Braves: Jon Lester Could Add Veteran Presence in 2021