BOSTON (CBS) — In a lot of ways, Jon Lester grew up during his time in the Boston Red Sox organization. He was drafted in 2002 when he was 18 years old, working his way up through the minors to make his MLB debut in 2006, establishing himself as a top-of-the-rotation starter for a championship team, and departing as a 30-year-old two-time World Series champion.
While Lester’s career took him to four other teams, Boston will always hold a special place in his life.
And on the day of his retirement announcement, Lester reflected on his time in the Boston organization with WBZ-TV’s Dan Roche.
“It’s pretty special to me, the way they treated me and my family when I went through all my cancer stuff was incredible,” Lester said, referencing his battle with lymphoma during his rookie season. “And then, just to get the opportunity to perform in Boston. I mean that’s obviously one of the Meccas of baseball. And to get to play in Fenway Park, consider Boston home for so long, it’s very special to me and my family.”
“It can be a hard place to play,” Lester added, “but it’s definitely worth it in the end.”
Among the things Lester is most looking forward to in retirement is bringing his children to see Boston this summer.
“I know my oldest remembers [Boston] a little bit, but the other two obviously don’t,” Lester said. “So it’ll be cool to see that.”
(Perhaps Red Sox ownership will impress the Lester children with a pregame ceremony for their dad, whenever that day may come.)
Outside of that trip, Lester doesn’t have too many plans in retirement — and that’s something he’s completely OK with.
“I think the unknown is great right now. I told somebody earlier that I think from the age of six or seven, my summers have been planned, every year. So to be able to kind of sit back and go, ‘Wow, we don’t have anything going on, I don’t have to train for this, I don’t have to be here on this date, we don’t have to move to this city at this time,’ is kind of nice to just kind of roll and see what’s going on,” Lester said. “The fact that I don’t have to worry about anything right now is, I think, the greatest pleasure that you can get.”
The 38-year-old said he knew midway through the 2021 season that he was likely wrapping up his career, but he kept it quiet and waited to make sure he was 100 percent sure. He said he’s happy that he can go out on his own terms.
“When it’s taken out of your hands, that was kind of part of the decision for me was I wanted to make sure it was in my hands to make that decision,” he said. “Like, I wanted it to be mine. I didn’t want it to be not getting a job or some other organization or whatever telling me I can’t do this anymore. So that was a big proponent of it. And I wanted to make sure I didn’t stick it out too long. I never wanted to play for numbers and I feel like now, with where I’m at, I’m probably not gonna get picked up for a contending team. It would probably be a middle team or whatever and I would just be playing for that stuff. And I don’t want to do that. I want to play and I want to win. So that was also another factor in it.”
While Lester’s role in helping the Cubs break their own World Series curse may be how the baseball world at large will first and foremost remember him, the 12 years in the Red Sox organization will always be the foundation upon which Lester’s long MLB career was built. And his role in the 2007 and 2013 championship runs are a part of history forever.
Roche asked Lester what he’d like to say to Red Sox fans.
“I think the biggest thing is just thank you. Thank you for all the support,” Lester said. “Like I said, we went through some really good times, went through some bad times, but we all came out at the other end, I think, better. And at the end of the day, I still talk about Boston. It’s a lot of people up there still family to me. So it was an awesome, awesome experience to play there, and obviously something I’ll never forget, and I loved being a part of the organization.”