Chicago Cubs: Jon Lester considering a return to Boston

With a shortened season and the end of his Chicago Cubs contract looming, Jon Lester is considering the prospect of becoming a free agent and heading back to Boston.

Before joining the Chicago Cubs and helping them win their first World Series in 108 years, Jon Lester was a fixture in the Red Sox rotation with two rings to his name. He even turned down an opportunity to rejoin Boston in order to move on to Chicago. Now, as he nears the end of his deal with the Cubs, it’s looking like he may be in line to go back to the team he began with.

Lester spoke at length with Rob Bradford of WEEI Sports Radio Network about what comes next for him after 2020. He talked with some uncertainty about his upcoming free agency and how his age and the Coronavirus pandemic would affect the deal he receives for 2021. The most interesting tidbit in the interview, however, was a seeming indication from Lester that he’d like to return to Boston.

"“I know I have the team option, the player option, that sort of thing. We’ll figure that out one way or the other. I will either be here or be a free agent. Obviously everything is open. I’m open-minded to anything. Absolutely it would be cool to go back and finish my career where it all started.”"

It’s hard to blame Lester for wanting to retire with the Red Sox. He spent over eight seasons in Boston, playing over half of his games there and posting a 120 ERA+. It’s also where he won his first two rings and had three of his five All-Star seasons, all while acting as Boston’s ace. He’s also well into the twilight of his playing days, struggling the past three years to post the typical number of innings that he used to.

That said, it will be a blow to the Cubs to see their best free agency acquisition ever leave town to retire with another team. The best year of Lester’s career came in Chicago with an impressive 171 ERA+ and a second-place Cy Young finish behind Nationals ace Max Scherzer. More importantly, he helped the team get over the hump and finally win a World Series title.

Whatever Lester does next is partly reliant on if and when this season will commence. He may have thrown his final pitch in a Chicago Cubs uniform, but he could still return in 2021 if he throws enough innings. The chances of him ending back in Boston, however, feel greater after this interview, assuming the feeling’s mutual with Chaim Bloom and the Red Sox front office.