From Fenway Fury to Full Confession: Lenny Clarke’s Most Hated Yankee

Lenny Clarke is undeniably one of the funniest people on the planet (and I’ll stand by that claim). With decades of experience as a headlining stand-up comedian, he's also well-known for his role as "Uncle Teddy" on the FX series Rescue Me.

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This weekend, Clarke is bringing his comedy to Connecticut, performing at Comix Roadhouse at Mohegan Sun on tonight (4/11/25) and Saturday (4/12/25). We had the opportunity to chat with Lenny from his hotel room at Mohegan Sun, and here’s our favorite moment from the conversation.

Lou: We missed an opportunity the last time you were on the show. You're a big Boston Red Sox fan—Dave and I are Yankees fans, Ethan's a Mets fan—everyone has their flavor. When the Yankees–Red Sox rivalry was at its peak, back in the late '90s to mid-2000s, which Yankee player did you most want to punch in the face?

Lenny: "Posada. I hated Jorge Posada. I don’t know why—I never met him. I met Jeter, I met A-Rod, I met a few of the other guys. And listen, my only hatred of the Yankees was this: you beat us every year. You beat us, you beat us, you beat us like a dog! We didn’t have a chance. You guys killed us. And then, when we finally won, it was over. I didn’t care anymore. And then we won a couple more. But those wins—we got what we needed. That was enough. It’s OK. I can die happy. What an organization the Yankees were. But Posada? I always hated him."

Oooh, good to hear as a Yankees fan because we loved Jorge for the very same reasons they hated him.

Anyway, I went on to tell Lenny how I hated Bronson Arroyo and then years later I got to interview him and it messed with my wiring because the dude is so cool.

You can listen to our complete interview with Lenny Clarke below.

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