The 2026=Cubs Convention kicked off last night, so there’s a TON to get into throughout the day today. We’ll get to all of it eventually. But first, I wanted to highlight what has become maybe my favorite thing to emerge from the noise: Jon Lester’s comments on what it means to be a Cubs Hall of Famer while waiting for “the call” to the MLB Hall of Fame.
In case you missed it, Lester was announced as one of two inductees into the Cubs’ Hall of Fame, which is, of course, a wholly earned and deserved honor. He’s also already a member of the Boston Red Sox Hall of Fame. And to him, that means more than the call to THE Hall will, if and when it comes.
He tried to explain that in a medium scrum from the convention, and I was just kind of blown away by what he had to say. Jon Lester is one of the most important Chicago Cubs of all-time, the ultimate competitor. But he’s also one of the better ballplayers of all time. So to hear him talk about this organization with such regard, and about his career with such humble confidence and certainty, is really something. I really think you’re going to like this.
Jon Lester on Waiting for The Hall of Fame
I’m not even doing it justice. The sincerity behind these words is palpable. This guy is the best.
Jon Lester on his Baseball Hall of Fame chances after getting into the Cubs Hall of Fame: “This, and the Red Sox….means more to me.” Should Jon Lester be a Hall of Famer? #Cubsconvention #Cubs pic.twitter.com/M0ynKH6DzT
— ESPN Chicago (@ESPN1000) January 17, 2026Here’s a rough transcription for those unable to listen:
“My kids don’t really remember a lot (of my career), and so we’ve gone down some rabbit holes of like, hey, your dad was actually okay (laughter). And so I got to thinking one night, how many years did I not go to the playoffs, right? I think it was two or three. My whole career. 16 years. At the end of the day, if that gets me into the Hall of Fame, cool. If it doesn’t, I’m happy driving carpool every morning, dropping them off.
Like, to me, getting (inducted into the Cubs Hall of Fame) tonight and getting the Red Sox is … I don’t want to say more important to me, because it’s not. But it means more to me. Because this organization and the Red Sox organization value what I did, right?
You get into the Hall of Fame, nothing against you all, y’all are writers. Writers vote on it, right? They never saw me in the clubhouse. Does that make sense? So, I care that the (Cubs and Red Sox) organizations have done this … it’s a huge honor with two historic franchises. At the end of the day, the Hall of Fame for me is getting that cherry on the top of your sundae. I’ve got my sundae built right now. Being a part of this and the Red Sox. If that call (from the Hall comes), that’s the cherry.
You know what I’m saying? I didn’t play the game for that. I played the game because I loved it. I played the game because I loved to compete. I played the game because it was fun. I know it didn’t look that way for me sometimes when I was out there. But I loved the competition…
But if that call doesn’t come, that doesn’t change the way I feel about my career.
Jon Lester, 42, played his last big league season in 2021 (we won’t mention for which team he threw his final pitch…), though it did come against the Cubs, which is fun. And that means he will first become eligible for the Hall of Fame on the 2027 BBWAA ballot.
From the perspective of raw, on-field stats alone, he’s a borderline candidate. “Only” a 5x All-Star, “only” one no-hitter, never a Cy Young award winner, etc. He just doesn’t have, say, Justin Verlander’s career. HOWEVER, that’s only half the battle. While his stats won’t carry him into the Hall, they are definitely good enough to warrant his position when you also consider the narrative: EVERYONE knows Jon Lester is one of the greatest big game and postseason pitchers in history. He has three World Series titles for a reason.
I mean, the dude has almost a FULL SEASON worth of playoff innings in his career: 26 starts, 11 more appearances out of the bullpen, 154.0 IP with a 2.51 ERA!
With that as the backdrop, plus the stats, plus a great reputation, plus a very long career, I think Jon Lester will eventually make it into the Hall of Fame. For now, though, he’s happy to be honored by the two organizations that knew him best.
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