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We haven’t even hit the first full Saturday of college football yet, and Barstool Sports founder Dave Portnoy has already suffered what will likely go down as one of the most embarrassing gambling losses of the year. On Thursday afternoon, Portnoy took to social media to make what he said might be his “strongest play of the year” as he picked Rutgers to cover a 29.5-point spread over UMass on Thursday night in what he expected to be a blowout. “I made my 1st bet of college football season and it may be my strongest play of the year. Rutgers -29.5 to beat umass by 40 plus,” Portnoy wrote in a post on X. I made my 1st bet of college football season and it may be my strongest play of the year. Rutgers -29.5 to beat umass by 40 plus — Dave Portnoy (@stoolpresidente) September 3, 2026 To be fair, the game was indeed a blowout, just not in the way that Portnoy expected. UMass, which was projected to be the worst FBS team in the country by nearly every advanced predictive metric, blasted Rutgers 37-21 in a game that frankly wasn’t as close as the final score suggests. At one point in the third quarter, UMass led by a score of 30-7. UMass is annihilating Rutgers! Rutgers entered the game as a 29.5-point favorite. Jason Horowitz and Anthony Herron have the Big Ten Network call. 🏈🔥🎙️pic.twitter.com/g8AaCmoAGl — Awful Announcing (@awfulannouncing) September 4, 2026 To Portnoy’s credit, he did own up to the atrocious pick before the game even reached halftime. “Alright hand up, I gotta be a leader right now – we need more leaders in this country,” Portnoy said in a video posted on X. “I gave out Rutgers as my pick of the week, -29.5. I said, ‘I think this pick is so easy, it might be the pick of the year’ – and I believed it. I put my hard-earned money on it with DraftKings. “Well, they’re down 24-7; it could be 54-7.” “I’m not going to point the finger at (Greg) Schiano; I’m not going to point the finger at Rutgers football, which is the most embarrassing group of losers I’ve ever seen,” Portnoy continued. “I’m going to point the finger at me, and say ‘Dave, you’re a f*cking moron, and you’ve gotta be better.’ And I deserve Freezing Cold Takes to retweet me and put me on a poster.” Freezing Cold Takes did, indeed, put Portnoy on a poster before the game even reached halftime. It took me 3 minutes into the college football season to get freezing cold taked https://t.co/XocWgb2Vol — Dave Portnoy (@stoolpresidente) September 3, 2026 “That was the worst pick,” Portnoy said. “It’s a long football season. I’ve got to be better.” “Hand up, that’s the most embarrassing thing I’ve done in 24 years of Barstool,” Portnoy said. “I’m talking anything.”