Red Sox, Cubs pitcher Jon Lester retires after 16 years, 3 World Series titles

After a 16-year career, pitcher Jon Lester told ESPN on Wednesday that he's decided to retire from baseball.

"It's kind of run its course," Lester, 38, told ESPN. "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."

Lester's career has been studded with major achievements. He's been an All-Star five times, finished in the top 5 of Cy Young voting three times, and tossed a no-hitter. He won three World Series titles, including one with the curse-breaking 2016 Chicago Cubs. He pitched for five different teams, but spent the vast majority of his career with the Boston Red Sox and the Cubs.

It was a career that almost never got off the ground. The Red Sox drafted him in 2002, and he'd made his MLB debut by 2006, but a discovery that summer brought everything to a screeching halt. What Lester thought was a back problem was actually enlarged lymph nodes caused by lymphoma.

Fortunately, the cancer was treatable. He underwent chemotherapy during the offseason and returned to the Red Sox in the summer of 2007, making his first post-cancer start in late July. Later that year, he made his first postseason start in Game 4 of the World Series, leading the Red Sox to a title-clinching victory. A few years later, Lester played a key role in the Sox's 2013 championship. He started Games 1 and 5 of the World Series, pitching nearly eight innings in each game and allowing one total run.

Sep 26, 2020; Chicago, Illinois, USA; Chicago Cubs starting pitcher Jon Lester (34) reacts against the Chicago White Sox during the first inning at Guaranteed Rate Field. Mandatory Credit: Mike Dinovo-USA TODAY Sports
Red Sox and Cubs pitcher Jon Lester has decided to retire after a 16-year career. (Mike Dinovo-USA TODAY Sports)

Lester helps Cubs make history

Lester's stint with the Cubs is straight out of a movie. After finishing 4th in Cy Young voting in 2014, he signed with Chicago before the 2015 season, when the Cubs were a last place team. The presence of a top pitcher helped recruit others to join the Cubs, and they went from a 73-win team in 2014 to a 97-win team in 2015.

The next year, Lester and his 2.44 ERA finished second in Cy Young voting and the Cubs won 103 games en route to the franchise's first World Series title in 108 years. Lester started Games 1 and 5 of the World Series and pitched three innings of relief in the fateful Game 7. Lester would go to the playoffs with the Cubs two more times, with his final appearance coming in the 2018 wild-card game, a 2-1 loss to the Colorado Rockies.

Lester became a free agent after the 2020 season, which ended up being his worst season in the majors (5.16 ERA in 61 innings). He signed a one-year contract with the Washington Nationals, who ended up trading him to the St. Louis Cardinals, the final stop on his major-league journey. Over his 16-year career, Lester had a 3.66 ERA and exactly 200 regular season wins.

"The part that helped me be OK with this was quarantine," Lester said about his decision to retire. "I was home, at a time of the year I wasn't normally home. That opened my eyes. ... When the work outweighs the joy, then it's kind of time to reevaluate where you're at."

As far as what's next, Lester didn't give ESPN many details. He said he's definitely not going into full-time coaching, but would consider some TV work, which is what his former personal catcher and current Cubs manager David Ross did following his retirement.