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Chris Gotterup Reveals Jim Irsay Surprised Him With a $100,000 Cash Match Against JB Holmes

Chris Gotterup shared a wild story about the late Colts owner Jim Irsay during his appearance on Pardon My Take Thursday.

Gotterup said his agent had a longstanding relationship with Irsay, who purchased a private golf course in Culver, Indiana, and regularly invited pros out to play it. Gotterup said he only felt comfortable sharing the story now that Irsay has passed.

“My agent was always telling these crazy Irsay stories,” Gotterup said. “And I was like, no way, that’s true?”

Gotterup said he and JB Holmes were out at the course to play a casual round when Irsay showed up unannounced in full getup, comparing his appearance to “the Undertaker.” Irsay then changed the plans on the spot.

“He goes, ‘All right, change of plans. $100,000 cash, you versus JB, we’re all gonna watch,'” Gotterup said.

Gotterup, who was playing on the Korn Ferry Tour at the time, said he had never played for stakes anywhere close to that in his life, calling it the most high pressure match he’s ever been part of. He ended up bogeying the final hole and losing to Holmes.

Irsay reportedly upped the ante further, offering another $10,000 bonus to either player who could accurately call the score they were about to shoot. Gotterup said his brother, his agent, and roughly 30 other spectators were on hand to watch the impromptu match unfold.

“It was the craziest shit ever,” Gotterup said.

Gotterup added that Irsay treated the two golfers to a Colts game following the match, flying them out on the team plane and hosting them in his personal owner’s box.

Irsay owned the Colts from 1997 until his death on May 21, 2025, at age 65. He purchased the Culver course, known as Horseshoe Farms and formerly Mystic Hills Golf Club, in 2019.