![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://images.squarespace-cdn.com/content/v1/5f6d242de2df5d2ce9cb52a9/1618832779709-54991CV0E4LG57RM0MG6/IMG_1686.JPG)
MLB — Coley Harvey Blog — Coley Harvey
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://www.usatoday.com/gcdn/-mm-/42cb2ab39386d022d7e20e94b6878b14f637e89c/c=0-214-4256-2619/local/-/media/2014/12/15/USATODAY/USATODAY/635542763820923158-lester.jpg)
Nightengale: Lester lured by Cubs misery, history
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://images2.minutemediacdn.com/image/fetch/https%3A%2F%2Fdawindycity.com%2Fwp-content%2Fuploads%2Fgetty-images%2F2018%2F08%2F460503436.jpeg)
Chicago Cubs: Lester best free agent signing in franchise history?
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://cdn.vox-cdn.com/thumbor/KsWh7ry4CKwb9w1DpbAjm5Accfw=/0x0:3656x2664/1200x800/filters:focal(1279x221:1863x805)/cdn.vox-cdn.com/uploads/chorus_image/image/70378724/1271262279.0.jpg)
MLB Rumors: Jon Lester has retired - Lone Star Ball
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://img.mlbstatic.com/mlb-images/image/private/ar_16:9,g_auto,q_auto:good,w_1024,c_fill,f_jpg,dpr_3.0/mlb/pis8picxzrrvr91wmyck)
Cubs could add pitching in Kyle Schwarber deal
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](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-2F2017-2F07-2F826040464-850x560-a0f68b2ae517c7b026905bba0094dcb6.jpg)
Cubs: Remembering Jon Lester's unexpected first career home run
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://4.bp.blogspot.com/_Ew6WPsZoch4/SV-hsgQwdhI/AAAAAAAADGI/ybCOxMkHF5g/w1200-h630-p-k-no-nu/casey+06T+IMG.jpg)
Brush with greatness: Sean Casey
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://s.yimg.com/ny/api/res/1.2/3m2XRpqEq6ffCzYamQSGJQ--/YXBwaWQ9aGlnaGxhbmRlcjtoPTY2Ng--/https://s.yimg.com/os/creatr-uploaded-images/2021-01/cb12ef70-602e-11eb-97c7-b7428450ec0e)
MLB free agent tracker: Where every star signs, and what the deal
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://img.mlbstatic.com/mlb-images/image/private/ar_16:9,g_auto,q_auto:good,w_1024,c_fill,f_jpg,dpr_3.0/mlb/chhgod6vdg3i6d2hlmhj)
Cubs could add pitching in Kyle Schwarber deal
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://img.bleacherreport.net/cms/media/image/c8/3e/77/42/0cf7/46b4/bbf2/d8905a9657ca/crop_exact_GettyImages-1044863024__1_.jpeg?h=1458&q=90&w=2187)
Jon Lester Major League Baseball, News, Scores, Highlights
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://imageio.forbes.com/specials-images/imageserve/61e329443d645415bff5226f/Left-handed-pitcher-Jon-Lester-pitching-for-the-Boston-Red-Sox-at-Fenway-Park-/960x0.jpg?height=480&width=711&fit=bounds)
Jon Lester's 16-Year Career Perfectly Blended Intensity And
![Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs, Sports](https://ballnine.com/wp-content/uploads/2021/09/Spitballin_Tewksbury_Feature.jpg)
Bob Tewksbury - BallNine