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.

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 th

See Full Page