Papa Hops is one of those Chicago summer institutions that's bigger than any one team's record. The 16-inch softball tournament, now in its 12th year at Kennedy Park, pulled an estimated 7,500 people out to the South Side this year, all in honor of the late Tom Hopkins and to raise money for local families battling cancer. Big Cat has been part of the tradition for years, even singing the National Anthem before the championship game. But for Barstool Chicago's own squad, showing up isn't the same as winning, and this year's edition ended the same way recent ones have: with the guys scrambling for answers instead of hoisting anything.
The Barstool Chicago softball team is scrambling for answers after another disappointing finish at Papa Hops.
That kind of blunt admission from the account itself tells you this isn't a one-off gripe. Papa Hops has apparently become a recurring gut punch for the Barstool Chicago roster, and the crew wasted no time turning the loss into podcast material. The Stretch dropped a new episode in the immediate aftermath, and the framing was less "how did we lose" and more "how do we make sure this never happens again."
New @thestretchpod is live Big Cat is ready to pay top dollar for 16 inch softball players for next year
The pitch, according to the pod, is straightforward and very Big Cat: if the roster can't get it done on heart alone, buy the heart. Whitesoxdave framed it as Big Cat personally bankrolling a run at a 16-inch championship next summer, which is either the most sensible front-office move in recreational softball history or an excuse to spend money on beer-league free agents. Probably both.
New @thestretchpod is live on the heels of Papa Hops, a Sox sweep, the MLB draft and more We’re buying a 16” championship next summer. And by “we” I mean @BarstoolBigCat Tune in: t.co/tvZoGMlDhQ
None of this is happening in a vacuum, either. Big Cat's got a bigger Wrigley Field moment on the calendar next Monday, tied to receiving some kind of ceremonial check, and he's reportedly already angling to run a one-day 51/49 raffle at the ballpark and personally sell tickets during the first few innings. It's the same instinct on display: see an opportunity, go big, worry about logistics later. Whether that same energy translates into an actual softball championship next July is the real question hanging over the Barstool Chicago crew right now.
Big Cat is receiving his big check next Monday at Wrigley!!! “And on top of it I convinced the Cubs we’re gonna do a one day only 51/49 raffle and I’m gonna be selling tickets for the first couple of innings” -Big Cat
For now, the Papa Hops disappointment stings the way losing at a charity tournament always does: it's not really about the standings, it's about bragging rights on the South Side for the next 12 months. Barstool Chicago will have to sit with this finish until next summer rolls around. But if Big Cat's serious about outspending the competition on 16-inch talent, the rest of the Papa Hops field should probably start paying attention now instead of waiting until next July to find out what that actually means.