Dave Portnoy places $5,000 bet on Bryce Underwood to win Heisman Trophy after entering Columbus

Dave Portnoy is putting his money where his mouth is. On Thursday, the Barstool Sports founder and avid Michigan fan posted a screenshot of his $5,000 bet for Wolverines quarterback Bryce Underwood to win the Heisman Trophy this season.

If the bet hits, Portnoy will walk away with a hefty $255,000 payday. Underwood has +5000 odds currently to win the coveted individual award, according to BetMGM.

In fairness, Underwood hasn’t played a snap of college football quite yet. Alas, Underwood was the No. 1 player in the 2025 recruiting cycle and will be the first freshman quarterback to start for Michigan since Tate Forcier did so in 2009.

Portnoy’s bet on Thursday isn’t the first time he’s invested in Underwood. The media icon reportedly played a significant role in Michigan landing the five-star QB during his recruitment last year.

“I got a call from the Michigan football team,” Portnoy said on the Barstool College Football Show. “They said, ‘Hey, there’s this donor who wants to talk to you. I said that I’m doing this [landing Underwood] by myself and I don’t need to talk to anybody.

“They said, ‘Please, this woman is a big fan of Barstool and you; she’d love to talk to you. Her name is Jolin.’ … They said her husband is a guy by the name of Larry Ellison, you ever heard of him?”

Larry Ellison is the co-founder the software company Oracle Corporation and is considered one of the wealthiest people on the planet. Portnoy met with Ellison and Jolin over Zoom, and Bryce Underwood committed to Michigan in November.

Now, the 18-year-old is poised for a breakout season. In fact, Michigan head coach Sherrone Moore raved about Underwood’s potential earlier this week.

“Probably halfway through camp, I was like, ‘Ah, this guy’s pretty good,'” Moore said. “‘I think this guy might be the guy.’ Had a scrimmage, and I think it was the first time we went to the stadium, he made a couple of throws, and I just looked at Chip [Lindsey], and he nodded at me.

“Looked at Coach [Biff] Poggi, who was behind me, like, ‘Yeah, I think this is the guy.’ But you wanted to see him do that every day, every practice, every time we went in the stadium.”

Evidently, Underwood did just that, considering Michigan named him its QB1 on Aug. 24. Underwood will make his debut for the Wolverines on Saturday when they square off against New Mexico at 7:30 p.m. ET. The game will air live on NBC.