Seeing Jon Lester back in Red Sox camp is a reminder of how he feels about the Cubs

It caught me a little off guard this week when images of Jon Lester at Red Sox camp popped up on Instagram - and I'm not sure why. I probably still think of the Cubs when I think of Lester and who could blame me given the role he played during his time here?

Lester, who retired following the 2021 season, ended his career with exactly 200 regular season wins. But he's probably known best for his postseason resume and three World Series championships and rightfully so. One would have hoped he'd be back in camp with the Cubs, continuing his tutelage of Justin Steele, but instead, he's back in Boston threads - a sign of how he's feeling about Chicago at this point.

A Cubs connection helps bring Jon Lester back to the Red Sox

Of course, there's a new Cubs connection in Boston in the form of the team's new Chief Baseball Officer Craig Breslow, who took over Red Sox baseball operations this winter. The two were teammates during their playing days and Breslow wasted no time bringing Lester back into the fold as a guest instructor at camp.

“I was excited. I think, ultimately, when you’re done playing, you still want to be a part of something,” Lester told MLB.com. “So it was nice to get a phone call and text saying, ‘Hey, we want you to come be a part of this.’ It's a good feeling. I think anybody in life just wants to be wanted, right? So it's nice to be wanted, and have your presence appreciated around these guys.”

Just a few months removed from the firing of his longtime personal catcher David Ross, Lester probably wants to let things calm down before he immediately embraces the Cubs and Jed Hoyer. Earlier this winter, he noted a 'waned' enthusiasm toward the club following Ross' firing. Hopefully, with some time, the five-time All-Star will warm up on a return to Chicago in some capacity but, for now, it seems like space is the best thing for everyone involved.