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Jon Lester retires: Five-time All-Star and three-time World Series
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.pressherald.com/wp-content/uploads/sites/4/2014/07/Royals-Red-Sox-Baseba_Acco.jpg?w=766)
A head-spinning day of deals for the Red Sox
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.courant.com/wp-content/uploads/migration/2014/12/11/HS3RI253DBBLJLUFN4M6KFFRU4.jpg?w=620)
With Jon Lester signing, Cubs shake up the baseball world
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.courant.com/wp-content/uploads/migration/2014/12/11/23MVBTE4SFGSBC5BGMK2RLGT5Y.jpg?w=620)
With Jon Lester signing, Cubs shake up the baseball world
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.pressherald.com/wp-content/uploads/sites/4/2014/07/All-Star-Game-Basebal_Acco4.jpg?w=1024)
A head-spinning day of deals for the Red Sox
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.bostonglobe.com/resizer/YjO283osdJkbCtYjKvF0qyi90pA=/arc-anglerfish-arc2-prod-bostonglobe/public/AV2IOEOIQQFFJBI5PDHKYS4KPM.jpg)
Jed Lowrie debuted with the Red Sox in 2008, and he's still going
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://bloximages.chicago2.vip.townnews.com/eagletribune.com/content/tncms/assets/v3/editorial/4/24/4240de0a-fa6a-11ec-870d-9f5f5b96c07d/53e8bd0b792e5.image.jpg?resize=762%2C500)
Two cities, one legend: Jon Lester reflects on one of a kind
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.chicagotribune.com/resizer/os2d1xmvymiP4ScvaQJqkmTjyts=/arc-anglerfish-arc2-prod-tronc/public/ZWSX5MEDWJAS3EA3U3RSFFG2XU.jpg)
Column: Why Chicago Cubs should retire Jon Lester's number
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://cdn.vox-cdn.com/thumbor/M0h9iT0Hmy1u0r4fyf5CF3eawlg=/1400x1400/filters:format(jpeg)/cdn.vox-cdn.com/uploads/chorus_asset/file/22874421/1235447854.jpg)
Outside the Confines: MLB News Yankees Red Sox - Bleed Cubbie
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://img.mlbstatic.com/mlb-images/image/private/t_16x9/t_w1024/mlb/wg6imal9yd6q6yr2qyng)
Jon Lester returns to Wrigley Field
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://www.si.com/.image/ar_4:3%2Cc_fill%2Ccs_srgb%2Cfl_progressive%2Cq_auto:good%2Cw_1200/MTc4MzMxNTM2MDA3ODk4NzI4/jon-lester-chicago-cubs.jpg)
Jon Lester retires after epic MLB career as Red Sox, Cubs ace
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://bloximages.chicago2.vip.townnews.com/eagletribune.com/content/tncms/assets/v3/editorial/0/5b/05bc5d60-fa6a-11ec-94ff-5705d32894f5/53e8c3f47b3ad.image.jpg?resize=617%2C500)
Two cities, one legend: Jon Lester reflects on one of a kind
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://img.mlbstatic.com/mlb-images/image/private/t_2x1/t_w1536/mlb/a03odxprt3ie49ro2tne.jpg)
Jon Lester returns to Wrigley Field
![Jon Lester would welcome a Red Sox-Cubs World Series - The Boston Globe](https://baseballegg.com/wp-content/uploads/2021/02/jon-lester-red-sox-370x315-1.png)
Jon Lester doesn't appear to care about his Hall of Fame chances