![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://www.sj-r.com/gcdn/authoring/2014/12/15/NSJR/ghows-LS-0a085a3e-3555-4914-e053-0100007f9e01-492852c6.jpeg)
Lester hopes to end Cubs' century-plus drought
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://media.bleacherreport.com/image/upload/v1675870287/ju6x4lj5hur102y2gzun.jpg)
The Best 5-Year Stretch for Every MLB Team in Modern History, News, Scores, Highlights, Stats, and Rumors
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://americancenturychampionship.com/wp-content/uploads/2022/05/Lester.jpg)
Jon Lester
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](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
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://static01.nyt.com/images/2021/03/29/sports/29mlb-capsules-top1/29mlb-capsules-top1-videoSixteenByNine3000.jpg?year=2021&h=1688&w=3000&s=e3b736725941d76cf81810ba1e2658dda105632eb862fa479bf3d18c51508051&k=ZQJBKqZ0VN&tw=1)
2021 MLB Season Preview: Team-by-Team Capsules - The New York Times
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://a1.espncdn.com/combiner/i?img=%2Fphoto%2F2022%2F0111%2Fr960488_1296x729_16%2D9.jpg)
Maybe the best playoff pitcher ever' - What made Jon Lester an October legend and potential Hall of Famer - ESPN
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://media.bleacherreport.com/image/upload/c_fill,g_faces,w_1600,h_1600,q_95/v1634247920/l9ruchdaenbl7ao1crki.jpg)
Jon Lester Retires After 16 MLB Seasons; Won 3 World Series with Red Sox and Cubs, News, Scores, Highlights, Stats, and Rumors
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://images2.minutemediacdn.com/image/upload/c_fill,w_1440,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/5b0746530b06b5e75b99b491a2f3610448688e7c1c6fd5fd577e00b97eb027a4.jpg)
Longtime Red Sox and Cubs ace Jon Lester announces retirement
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://talkingpointssports.com/wp-content/uploads/2022/01/jon-lester.jpeg)
Jon Lester Calls It A Career
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://static01.nyt.com/images/2016/11/04/sports/03webross1/03webross1-videoSixteenByNine3000-v2.jpg?year=2016&h=1688&w=3000&s=f30240bb024cb47f8a3a3279588c2f27e258661333bf6aac7000402745a3a568&k=ZQJBKqZ0VN&tw=1)
David Ross, Oldest Player in World Series, Ends Career in Climactic Game 7 - The New York Times
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://2cic.nyc3.cdn.digitaloceanspaces.com/c/stories/21/baseball/stroman_brad_penner-750.jpg)
Chicago Cubs News: Stroman offers Rolex watches to former teammates, Lester retires
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://img.mlbstatic.com/mlb-images/image/private/t_16x9/t_w640/mlb/eyrdffxmyqv1leux5zeb)
Jon Lester remembered for World Series Game 5 with Cubs