Jon Lester announces retirement after 16 seasons, three World Series titles

Three-time World Series champion and 200-game winner Jon Lester is retiring after a 16-year career.

Lester, 38, told ESPN that his body just isn’t up for the rigors of a major league season anymore. He made 30 or more starts 12 times during his career and 28 during his final season split between the Washington Nationals and St. Louis Cardinals.

His résumé contains five All-Star appearances and a 2.51 postseason ERA.

“It’s kind of run its course,” Lester said. “It’s getting harder for me physically. The little things that come up throughout the year turned into bigger things that hinder your performance.

“I’d like to think I’m a halfway decent self-evaluator. I don’t want someone else telling me I can’t do this anymore. I want to be able to hand my jersey over and say, ‘Thank you, it’s been fun.’ That’s probably the biggest deciding factor.”

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Lester leaves a legacy of postseason success.

He acquired two World Series titles with the Boston Red Sox in 2007 and 2013 and a third ring with the Chicago Cubs in 2016, helping break a 108-year title drought. Additional playoff appearances in 2008, 2009, 2014, 2015, 2017 and 2018 made him an October fixture.

Those memories will shine brightest for Lester.

In his prime, the 6-foot-4 Lester dominated with a nasty cutter and intimidating presence on the mound, which included his patented look: glove resting just under his chin as he stared in for signs from the catcher.

“The cutter is what neutralized me,” said Mark Teixeira, who along with Evan Longoria has the distinction of striking out more times than anyone else (22) against Lester. “He would go outside and see me diving over the plate, then he would come in with the cutter.”

“The reason that he was such a bulldog was he didn’t give in. And he wasn’t afraid to walk guys. He knew how to pitch the lineup.”

Lester is one of only nine modern left-handers with 200 wins, a .600 winning percentage and a career ERA under 4.00. Six of the other eight are in the Hall of Fame, while one, CC Sabathia, isn’t eligible yet.

Off the field, Lester was known as the teammate who united the clubhouse.

“If you’re building a baseball player, as far as how they treat other people, what their goals are, how you want them to compete and act on and off the field, he’s the model,” said Cubs manager David Ross, who was Lester’s personal catcher during the pitcher’s first two years in Chicago.

Lester signed a $155 million free-agent contract with the Cubs in 2015. The decision to sign with a last-place team wasn’t easy.

“Him taking a chance on us when he did set the stage for everything that came,” then-general manager Jed Hoyer said. “He was clearly only coming here for one reason, and everyone knew it.”

Lester called signing with the Cubs “the single biggest decision we’ve ever made in my pro career,” though he struggled in his early weeks in Chicago, with a 6.23 ERA in April 2015.

In his second year in Chicago, Lester went 19-5 with a 2.44 ERA and was named National League Championship Series co-MVP. He pitched three times in the World Series versus Cleveland, including a relief appearance in Game 7, on his way to a third World Series ring.

It was the start of a remarkable postseason stretch. From 2016 to 2018, Lester compiled a 1.93 ERA in 10 playoff appearances.

Lester began his career with the Red Sox in 2002 and made his big league debut in June 2006.

Late that season, back pain sent Lester to the hospital, where he was eventually diagnosed with anaplastic large T-cell lymphoma. He underwent chemotherapy but was able to return to the team midway through 2007.

Lester said he might consider television work and didn’t rule out coming to Cubs spring training to tutor young pitchers — but full-time coaching isn’t in the cards. He said he will miss many aspects of the game but knows he lived up to one commitment he made to himself.

“I never wanted fans to leave a game and ask, ‘Was the effort there?'” Lester said. “I think I always gave it.”