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Former Red Sox ace Jon Lester, three-time World Series champ, retires after 16 seasons

Jon Lester went 110-63 and won two World Series with the Red Sox.Jim Davis/Globe Staff

After 20 professional seasons and 16 big league campaigns that included 200 regular-season victories, five All-Star Game selections, three World Series rings — two with the Red Sox in 2007 and 2013, one with the Cubs in 2016 — and an emergence as a symbol of hope and strength for cancer patients, Jon Lester has decided to retire. A major league source confirmed the decision.

As recently as Tuesday morning in a conversation with the Globe, Lester was unsure of his decision.

“I tell people, I don’t want them to tell me when I’m done,” he said. “I want to give them the jersey and say, ‘Hey, thanks for everything. I’m out.’ I think there’s still that question, but I think there’s also the desire to still want to do it.”


Lester, who turned 38 last week, was taken by the Red Sox in the second round of the 2002 draft, the first overall selection of the team under what was then the new ownership. He reached the big leagues in 2006, debuting at age 22 for the Red Sox in a promising campaign in which he went 7-2 with a 4.76 ERA. However, that season came to a shocking conclusion when he was diagnosed with a treatable form of non-Hodgkin’s lymphoma in early September.

He returned by the middle of the 2007 season with an impressive six-inning performance in Cleveland on July 23. His return to the rotation that year culminated with 5⅔ shutout innings in Game 4 of the World Series against the Rockies, with Lester claiming the victory in the clinching contest.

The next year, he emerged as a dominant rotation force, crystallized by a no-hitter against the Royals at Fenway on May 19. He went 16-6 with a 3.21 ERA over 210⅓ innings that season, the first of 12 straight years in which he made at least 30 starts.


In 2009, Lester set a Red Sox record for a lefty with 225 strikeouts — a mark he reached again in 2010, his first of three All-Star seasons with the Sox. He finished fourth in Cy Young balloting that year.

Lester, who signed a five-year, $30 million deal with the Red Sox in the spring of 2009, became an organizational anchor for the Red Sox. He rebounded from the worst season of his career in 2012 (9-14, 4.82) to reclaim ace status for the Sox in 2013, going 15-8 with a 3.75 ERA and performing at a dominant level in the postseason, including a 2-0 record and 0.59 ERA with 15 strikeouts and one walk in the World Series.

The lefthander got off to the best start of his career in 2014, going 10-7 with a 2.52 ERA for the Sox through July. But the team plummeted from its title run to cellar-dwelling status. With Lester nearing free agency after a low extension offer (four years, $70 million) in spring training doomed negotiations (“We blew it,” principal owner John Henry reflected years later), the Sox dealt Lester and outfielder Jonny Gomes at the trade deadline to the A’s for outfielder Yoenis Cespedes and a draft pick. (Cespedes and the pick were packaged after the season in a deal with the Tigers for Rick Porcello.)

Lester pitched well in Oakland, then signed a landmark six-year, $155 million deal as a free agent with the Cubs. (The Red Sox offered a six-year, $135 million deal.) Acquired as a centerpiece of a building team, Lester emerged as a force for the Cubs, particularly in the team’s World Series run in 2016.


That year, he followed an All-Star regular season (19-5, 2.44) with a 2.02 ERA in 35⅔ postseason innings, a run that included NLCS MVP honors and key contributions in the World Series, including a three-inning bullpen appearance in Game 7 for the first Cubs title in 108 years.

That performance cemented Lester’s place in Cubs history while also defining him as one of the top postseason pitchers of his generation. In his career, he made 26 postseason appearances (22 starts), going 9-7 with a 2.51 ERA in 154 innings.

Lester remained effective if not as dominant for Chicago over the next four years. He reached free agency after the 2020 campaign, signing a one-year deal with the Nationals, who fell out of contention and traded him at the end of the season to the Cardinals. Lester went 7-6 overall with a 4.71 ERA, and with a six-inning, two-run effort on Sept. 20, he won his 200th career game, becoming one of just seven pitchers this century to reach that plateau.

Still, Lester recognized that the challenge of pitching at a level to which he’d become accustomed had become more daunting. On Tuesday, he said he had not yet become reflective about his 20 years in the game, but saw such a time coming in the near future.


“There will come a time where it’ll all hit me, maybe when I am done and kind of decide and make sure that that’s the right decision and then be able to kind of step back,” said Lester. “In the offseason, you’re still kind of in that mode [where] playing next year, I’m looking forward to that. So you really haven’t shut down.

“[But] maybe when I am done and have that summer to sit around and watch baseball, as opposed to being in the grind and being worried about the next start and so forth, I’ll be able to kind of hopefully appreciate it a little bit and sit back and think about it.

“But it really hasn’t hit me. My dad brings it up to me every once in a while. He’s like, ‘God, this is your whatever year. I can’t believe it. Did you ever think this would be you?’

“It still surprises me that I’ve been able to do it as long as I have. I’m very grateful and thankful for the opportunity to do it.”

Alex Speier can be reached at alex.speier@globe.com. Follow him on Twitter at @alexspeier.