Technically, I suppose the Jon Lester stories don’t “keep on coming,” since they are all from his episode on the ‘Lovable Reunion’ podcast with Anthony Rizzo and David Ross. But the stories do keep getting clipped, as podcasts do these days, and they seem to land all the more that way.
We already talked about Lester’s unbelievable – but real! – tale of drunkenly negotiating David Ross’s contract with Cubs President Theo Epstein at 2am from a bar, and there are a couple more to share.
Another one involves the magic elixir of beer, which we’re quickly learning is the real secret to winning it all, and arguably the most thrilling regular season game in Cubs history:
Jon Lester came in for a walk-off, suicide squeeze attempt, “a few pops deep” ???“Because you were always for the boys” ? pic.twitter.com/tylNrTfsUk
— Lovable Reunion (@LovableReunion) April 9, 2026The headline there obviously is about the starters having some rally beers to help aid in the comeback (because why would starting pitchers think they would ever be needed in a game like that?), and Lester laying down the game-winning, walk-off, sac bunt to complete the comeback. But what’s maybe more interesting is the level of personal involvement from Theo Epstein, both in deciding to have Brian Matusz take that spot start, and in coming down to the clubhouse to discuss the game after the fact.
We know there are always stories behind the stories, but we rarely get to hear them in a way that offers insight into the inner workings of baseball ops. Into the delicate, but important, relationships between the executives, players, coaches, and manager. We keep it relatively simple and superficial talking about this stuff on the outside – a spot start made sense back then at the time, it didn’t work out, but that’s OK because it gave us some of the greatest moments from the greatest season – but there’s always so much more to these stories.
The other story speaks to a moment in the 2016 season that too often gets forgotten. It’s true that the 2016 Cubs were a juggernaut overall, winning 103 regular season games and the division by 17.5 But there was a stretch, after their scorching start, where the Cubs actually lost 15 of 20 games, and the divisional lead shrank to 6.5 games in July. Still large, but hardly insurmountable.
The tension was probably as high as it was going to get that season, and Anthony Rizzo made an oopsie in discussing the situation with the media after a loss in Pittsburgh:
Jon Lester CHEWED out Anthony Rizzo over a quote, because he knew 5 minutes later they’d both be past it.That’s real brotherhood ? pic.twitter.com/9l3Ia9SyHc
— Lovable Reunion (@LovableReunion) April 8, 2026If a red-faced and angry Jon Lester was looming over me ripping me a new one, I would absolutely mess myself. I don’t care if I were as big as Anthony Rizzo. That’s terrifying.
The funny thing about that moment, with Lester letting Rizzo know that he need not be discussing the performance of the pitching staff publicly? That was THE END of that losing stretch. That’s right: the loss Rizzo is talking about in Pittsburgh was that 15th loss in 20 games. So, basically, Lester shredded Rizzo in the weight room, and boom, they won 21 of their next 27, and the divisional race was completely over.
More of the Lovable Reunion here, including the Jon Lester episode, a Joe Maddon episode, and the first one with just Rizzo and Ross.
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