![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://www.masslive.com/resizer/WHVMHsZHoQczRT_vr9HVip8uhqg=/800x0/smart/cloudfront-us-east-1.images.arcpublishing.com/advancelocal/CPPTQ5WBPNA73IL66P3XGJOOJU.jpg)
Jon Lester, former Boston Red Sox pitcher, retires after 16-year MLB career (report)
![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/https-3A-2F-2Fwhitecleatbeat-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2017-2F07-2F456616522-850x560-7f1156a0d58d1bc5c40cf4f77d0dfaad.jpg)
Former Oakland A's pitcher Jon Lester retires
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://www.si.com/.image/t_share/MTY4MTU2MTgzMjI3NzM3MzYx/2016-1007-jon-lester-si585_tk1_00455jpg.jpg)
Jon Lester retires after epic MLB career as Red Sox, Cubs ace - Sports Illustrated
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://ca-times.brightspotcdn.com/dims4/default/66bb88f/2147483647/strip/false/crop/5440x3627+0+0/resize/1486x991!/quality/75/?url=https%3A%2F%2Fcalifornia-times-brightspot.s3.amazonaws.com%2F39%2Fc4%2F931a078b481695ea0c9b4308f7b6%2F1257094-sd-sp-spring-training-007.jpg)
Padres pitcher Michael Wacha following up strong season with Red Sox - The San Diego Union-Tribune
![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_w1024/mlb/izid3bdig9tuj2c0vkwt)
Jon Lester Hall of Fame case discussion
![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/2017/10/16/NSJR/ghows-LS-5b96d1fd-7c30-3507-e053-0100007f21ca-95f1e397.jpeg)
Turner's home run gives Dodgers 2-0 NLCS lead over Cubs
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](http://res.cloudinary.com/ybmedia/image/upload/c_crop,h_1123,w_2000,x_0,y_234/c_fill,f_auto,h_1215,q_auto,w_2160/v1/m/b/b/bb32199b95d0d16dca4644deab9b24d009e76875/greatest-postseason-players-mlb-history.jpg)
The greatest postseason players in MLB history
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://upload.wikimedia.org/wikipedia/commons/thumb/5/54/Max_Scherzer_pitching%2C_March_30%2C_2023_%281%29_%28cropped%29.jpg/1200px-Max_Scherzer_pitching%2C_March_30%2C_2023_%281%29_%28cropped%29.jpg)
Max Scherzer - Wikipedia
![Jon Lester retires: Five-time All-Star and three-time World Series champion calls it a career after 16 seasons](https://ksltv.com/wp-content/uploads/2023/08/OKC-Dodgers-pitcher-Mike-Montgomery.jpg)
2016 World Series Hero Keeping Dream Alive In Minors
![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