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Dave Portnoy listed his five worst investments since founding Barstool Sports
Dave Portnoy doesn’t consider University of Michigan quarterback Bryce Underwood to be one of the worst investments he’s ever made. Podcaster Michael Rapaport, however, is a different story.
On the Pick’Em podcast, co-host Dan ‘Big Cat’ Katz asked Barstool Sports founder Dave Portnoy whether his role in Bryce Underwood’s recruitment to Michigan was his worst investment ever.
Dave Portnoy revealed the top five worst investments he’s made during his time at Barstool Sports and doesn’t consider Bryce Underwood among them
While Portnoy rejected the idea, he did name five things that were worse uses of his time and money.
According to Portnoy, the worst investments he’s made during his time at Barstool are: Brick watches, Michael Rapaport, Back to School, the “Mold house” (a Miami property that he purchased), and his racehorses.
“Back to School” was a 2010 Barstool Sports college campus concert tour that nearly bankrupted the company, while Rapaport — whom the company hired in 2017 — was fired after he tweeted an insult about the site’s fans and wound up suing the company for defamation. His claims were dismissed.
“Was your investment in Bryce Underwood the worst investment you’ve ever made?” -Big Cat
Dave: https://t.co/LUHWapUDzp
— Barstool Sports (@barstoolsports) October 22, 2026
The question stems from Portnoy’s connection to Underwood’s recruitment to the University of Michigan, which he was reportedly heavily involved in. Portnoy has also said he’s done putting up NIL money for Michigan after the experience with Underwood.
Underwood, the top-ranked quarterback in the 2025 recruiting class, flipped from LSU to Michigan with an NIL deal reportedly worth eight figures that was partially funded by Portnoy’s contributions. Portnoy publicly pledged and contributed millions to the effort alongside Jolin Ellison — wife of Oracle billionaire and Michigan alum Larry Ellison — to outbid LSU’s reported $1.5 million-per-year offer.
His sophomore season has been rocky, however, as he was benched at halftime of Michigan’s game against Penn State on Saturday after going 5-for-11 for 43 yards and two interceptions. He was replaced by true freshman Tommy Carr, the grandson of Lloyd Carr. Through six games, Underwood had 924 passing yards, a 58 percent completion rate, and eight turnovers.