Jon Lester Thinks It Would Be ‘Cool’ If He Finished His Career With The Boston Red Sox

Jon Lester of the Chicago Cubs reacts after allowing a double to Pablo Reyes of the Pittsburgh Pirates.
Justin Berl / Getty Images

While Jon Lester has at least one more season with the Chicago Cubs and it appears he would like to be with the team beyond the 2020 season, it isn’t clear whether the Cubs have an interest in him returning. Should he be forced to move on to another team, the Boston Red Sox could be an option.

Lester recently sat down for an interview with Rob Bradford of Boston’s WEEI. The two talked about where the pitcher thinks he’ll be at the start of the 2021 season. After saying he’d like to stay with the Cubs, he said he doesn’t know what will happen. There’s a player option and a team option and a $10 million buyout if the Cubs decide they don’t want him back.

“I will either be here [Chicago] or be a free agent. Obviously, everything is open. I’m open-minded to anything,” he said.

Lester then told Bradford he thought it “would be cool” if he finished his career where it started. While the idea of returning to the Red Sox intrigues the pitcher, he also said he has some time before he has to make that decision. The pitcher also said he doesn’t have any reason to believe the Red Sox would even want him back.

“Hopefully, I’m still a good enough caliber pitcher that the want of my services will still be out there for people,” he added.

Before the veteran pitcher starts looking ahead to 2021, there’s 2020 to deal with. The Chicago Cubs missed the playoffs last year for the first time since his debut season with the team. That caused the front office to fire manager Joe Madden and hire one of Lester’s best friends in the game — and former teammate — David Ross as the team’s new skipper. Lester is hoping to turn things around personally as well, since last year was his worst season since 2015. Last year, the pitcher went 13-10 with a 4.46 earned run average. That was his highest ERA since 2012.

If Lester does return to the Red Sox in 2021, it would be a homecoming to the team for whom he’s played the most seasons in his career. From 2006 to 2014, he won 110 games for Boston, compared to just 63 losses. He won at least 15 games five times in eight seasons before being traded to the Oakland Athletics in the middle of the 2014 season.

In 2015, he signed as a free agent with the Cubs. In 2016, Lester posted a career-best season, going 19-5 with a 2.44 earned run average. He also helped the Cubs win their first World Series championship in over 100 years.