Jon Lester reflects on Cubs tenure after his retirement, shares what he's most proud of in MLB career

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(670 The Score) Even Jon Lester can’t quite believe how his storied MLB career turned out.

“No,” Lester said with a laugh on the Parkins & Spiegel Show on Wednesday afternoon.

“To do at the level I was able to do it for as long as I was able to do it, if you would’ve told me that 15 years ago, I probably would’ve laughed at you. It’s a really special thing to me. That being said, I worked by ever-living butt off to do it and try to do it for as long as I did.”

On Wednesday morning, the 38-year-old Lester announced he’s retiring after an illustrious 16-year MLB career, over which he went 200-117 with a 3.66 ERA and was a five-time All-Star. Lester played in Chicago for six of those seasons, signing a six-year, $155-million contract before the 2015 campaign after getting the hard sell from Cubs executives Theo Epstein and Jed Hoyer, whom Lester knew well from their shared days with the Boston Red Sox.

Lester helped spearhead the Cubs’ rise not just with his on-field performance but his leadership in the clubhouse as well, and it culminated with a long-awaited World Series title in 2016 for the organization.

“I don’t think if Theo and Jed and all those guys (aren’t) with the Cubs that I necessarily sign with them,” Lester said. “I probably end up back with the Red Sox.

“Just the belief they gave me was incredible, the amount of confidence they had in their young guys that were going to come up.”

Lester was a three-time World Series winner, also earning titles in 2007 and 2013 with Boston. He was a premier performer in the playoffs, compiling a 2.51 ERA and 1.02 WHIP in 26 appearances, including 22 starts, in the postseason.

What Lester is most proud of in his career is his reliability. After fully establishing himself in the Red Sox’s rotation in 2008, he made 31 or more starts for 12 straight seasons. He also made a full set of 12 starts in the pandemic-shortened 2020 season and 28 more in 2021, when he split time between the Nationals and Cardinals.

“That’s the thing I’m most proud of, is the fact that I took the ball every five days,” Lester said. “Whatever they told me to do, I did. If I needed to change, if I needed to adapt, if I needed to do something more or less, we did it. But I think taking the ball was something that I was really, really proud of, and I was able to do it for a long time.”

Lester isn’t sure what will lie ahead in retirement. He’ll be happy to go visit the Cubs at spring training in Arizona – so long as it’s to hang out and golf. He isn’t interested in coaching.

“I don’t have anything on the schedule,” Lester said. “It will be my first summer off since I was 6 years old probably. It will be definitely nice. I’m sure it will be tough at times, but that’s just the nature of the beast.”