![Chicago Cubs starter Jon Lester and his playoff history](https://images2.minutemediacdn.com/image/fetch/https%3A%2F%2Fdawindycity.com%2Fwp-content%2Fuploads%2Fgetty-images%2F2017%2F07%2F1340802868.jpeg)
Chicago Cubs: Jon Lester reaches an incredible milestone
![Chicago Cubs starter Jon Lester and his playoff history](https://securea.mlb.com/assets/images/4/3/0/141132430/cuts/0804maddon1280_oeq7ss6j_jah78esh.jpg)
Playing stupid' no laughing matter for Cubs
![Chicago Cubs starter Jon Lester and his playoff history](https://ca-times.brightspotcdn.com/dims4/default/47ef63c/2147483647/strip/true/crop/2048x1366+0+0/resize/1200x800!/quality/75/?url=https%3A%2F%2Fcalifornia-times-brightspot.s3.amazonaws.com%2F08%2F37%2F285daa7ed54ac2e92a8df02c7993%2Flat-sp-jon-lester-lead-off-wre0043675326-20161024)
The puzzle of Cubs ace Jon Lester: He's hard to hit but easy to
![Chicago Cubs starter Jon Lester and his playoff history](https://static01.nyt.com/images/2016/10/21/sports/21NLCS1-cubs-keep-lead/21NLCS1-cubs-keep-lead-videoSixteenByNineJumbo1600.jpg)
Jon Lester, Unfazed by Antics, Brings Chicago Cubs to Cusp of
![Chicago Cubs starter Jon Lester and his playoff history](https://www.news-leader.com/gcdn/-mm-/a9e88494f07b0cf42c7e68a0d011afd231bdd75a/c=0-199-4170-2555/local/-/media/2016/09/14/Springfield/Springfield/636094697012000630-1.jpg)
rizzos-2-hrs-help-cubs-beat-cardinals-clinch-playoff-spot
![Chicago Cubs starter Jon Lester and his playoff history](https://americancenturychampionship.com/wp-content/uploads/2022/05/Lester.jpg)
Jon Lester
![Chicago Cubs starter Jon Lester and his playoff history](https://www.orlandosentinel.com/wp-content/uploads/migration/2014/12/11/5BU7D2WOXJBL3GTC2NJNWKVQAQ.jpg?w=620)
With Jon Lester signing, Cubs shake up the baseball world
![Chicago Cubs starter Jon Lester and his playoff history](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-2Fbosoxinjection-com-2Fwp-content-2Fuploads-2Fgetty-images-2F2018-2F06-2F979552458-850x560-9602616ceae2bde833d4825263c6c4ef.jpg)
Red Sox took the wrong road by not signing Jon Lester
![Chicago Cubs starter Jon Lester and his playoff history](https://www.nydailynews.com/wp-content/uploads/migration/2015/10/17/JPXMGKON5CXRSXLEWIGTNPH5BY.jpg?w=640)
October veteran Jon Lester takes ball in NLCS as Cubs' fall guy
![Chicago Cubs starter Jon Lester and his playoff history](https://imageio.forbes.com/specials-images/dam/imageserve/19f63f8837a74c10a11ca379f0979b8a/0x0.jpg?format=jpg&width=1200)
Jon Lester Is Top Free-Agent Signing In Cubs History -- Will Theo
![Chicago Cubs starter Jon Lester and his playoff history](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