Dave Portnoy has built a reputation not just as a digital media mogul but as one of the most flamboyant sports bettors in the game. Over time, Barstool Sports has evolved into a powerhouse of sports content, often walking the edgy line of bro culture and sports betting entertainment. But sometimes, even the king of swagger has to admit when the game isn’t going exactly according to plan. Speaking of games not going the way he’d like, the Syracuse vs. UConn football matchup has given Portnoy’s legendary betting confidence a real test.
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The ongoing game at the JMA Wireless Dome in Syracuse had been a tight, grinding affair. The score by the end of the third quarter had Syracuse still chasing the Huskies. It’s safe to say that the Huskies at the time were controlling key moments. And the disastrous part of this bet is that Portnoy is going to lose out on winning $39,047. That’s a massive 5-figure gamble where he had wagered $20,000. Portnoy candidly posts his betting receipt on X and writes, “The ‘Fold Nate Fold’ bet is in.”
Portnoy put down the over 57.5 points. He was expecting the two teams to light up the scoreboard and push past that 58-point mark. Knowing Portnoy, he was thinking fast-paced, offense-heavy, just the kind of game where the points flood in like a river. But by the end of the third quarter, reality started sinking in hard. The combined score was a measly 23 points. With Syracuse and UConn totaling less than half the anticipated points, the vibe changed quickly. For Portnoy, that end-of-third-quarter scoreboard was a giant flashing ‘Uh-oh.’ The odds of pushing the total points over 57.5? Slashed to nearly zero.
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But why did this happen? The Syracuse vs. UConn game had been a slow burner, with both teams locked in a defensive dogfight. Despite expectations for a high-scoring game, the scoreboard told a different story. By the end of it, both teams combined for a score of 47 points. Steve Angeli put up 417 yards with 2 TD. On the other hand, Joe Fagnano of the Huskies racked up 259 yards and no TD. On the running back side, Orange’s Yasin Williams had 11 carries for 48 yards, and he also scored a touchdown. UConn RB Jayden Brown had 5 carries for 72 yards and a TD.
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This mix of moderate passing from UConn and heavy yardage from Syracuse, paired with a decent but not explosive running game on both sides, nails why the game felt like a prolonged chess match. Honestly, Dave Portnoy should probably have waited a bit longer before dropping a five-figure bet on this one. It’s a tough pill to swallow, especially considering Portnoy’s incredible betting history with UConn basketball. Last season, he pulled off what he called “the greatest bet of my life,” putting down $600,000 on UConn to win the NCAA men’s basketball tournament. And that paid off huge, netting him a whopping $2.7 million when the Huskies dominated the competition.
Orange grit shines through in a nail-biting overtime victory
The Syracuse Orange versus UConn Huskies game turned out to be a rollercoaster of emotions and grit. Well, both for the fans and Dave Portnoy himself. And guess what? Syracuse managed to get away with a 27-20 victory in overtime that had everyone clutching their popcorn. For most of the game, things were rocky for the Orange. UConn held the lead for nearly the entire match, forcing Syracuse to chase points. Coach Fran Brown’s frustration was clear.
And especially about the team’s effort on the field. That’s why, after the final play, instead of allowing his players to soak in the win and head off celebrating, Brown gathered them and had them run extra sprints. The reason? There were moments in the game when the team looked like they were taking plays off. Syracuse rallied late in the fourth quarter to score their first lead of the game.
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Yasin Willis dashed into the end zone on a 3-yard touchdown run with just 48 seconds left. But UConn wasn’t done. They responded with a long 41-yard field goal with only one second remaining to tie the game and send it into overtime. It was in overtime where Syracuse’s persistence paid off, banging in a touchdown that sealed the deal. But on that final UConn drive, Syracuse allowed a key fourth-and-10 conversion on a jaw-dropping acrobatic catch by Skyler Bell, showing that this game was as much about resilience as it was about skill.
Ultimately Dave Portnoy lost a huge sum because of the slow offense both teams put forward. But the best part is Fran Brown can take a shower today!