It started as a bit and turned into a full-blown event. Barstool staffers didn't just talk about a Home Run Derby on a podcast, they built one, complete with a bracket, a scoreboard, and rotating commentary duties as guys got knocked out of the box.
TJ Hitchings kicked things off live for the Stool After Dark crew.
The setup was simple and very Barstool: whoever gets eliminated first grabs the mic. Big Cat laid out the ground rules himself, noting the loser rotates into the booth and the next guy steps in, which is exactly the kind of low-stakes structure that turns a backyard derby into appointment viewing. Before he even stepped in the box, Big Cat was already hedging, joking that some rando on Twitter told him where to stand last year and he couldn't remember if it was up or back in the box, and reminding everyone he's 41 with 3 kids and "still competing." Not exactly Bryce Harper energy, but he was out there swinging.
Meanwhile PFT Commenter showed up with his own concerns, tweeting that he was just trying to keep his hamstring in one piece heading into his round. It's the kind of injury report you'd never get from an actual MLB derby competitor, and that's the charm of the whole thing, real competitive stakes with zero athletic pedigree behind most of the participants.
Derby time. Just trying to keep my hamstring in 1 piece prayers up
But this wasn't just a bunch of media guys hacking away in a cage. Barstool's own account teased that bringing an MLB All-Star into the mix "just isn't fair," and the footage backs it up, a real bracket with live scoreboard graphics tracking swings and home runs between paired-off competitors, not some improvised backyard setup.
The bracket in action, with on-screen graphics tracking swings and home runs round by round.
As the rounds progressed, Big Cat gave updates from the booth, noting that Kipnis, presumably former MLB All-Star Jason Kipnis, found the barrel and helped push Round 3 along in real time. And the derby delivered its signature moment when Dana Beers put one into the night, clearing the target distance and advancing on the spot.
Dana Beers' derby-clinching blast, tracked live on the scoreboard, sent him through to the next round.
None of this was sanctioned, none of it was polished, and that's the point. Barstool has spent years building a culture where the line between the content and the guys making it disappears, and a self-organized Home Run Derby with rotating booth duty and hamstring anxiety is about as on-brand as it gets. Whoever wins the thing probably gets bragging rights and nothing else, but based on the energy in the bracket, that's more than enough.