Heading into the 2023 NFL season, the Buffalo Bills were once again considered one of the betting favorites to win the Super Bowl.
Things haven’t quite gone to plan, though. After a three-game winning streak pushed Buffalo to a 3-1 record, the Bills have dropped five of their last eight. The team went from a +900 NY sports betting contender – ranked third in the preseason – to +3000, well of the pace and potentially in danger of missing the playoffs entirely.
In terms of betting, the Bills have also disappointed many. Buffalo has been favored 10 times this season, going 6-4 straight-up in those games and 4-7 against the spread. They have lost in games they arguably shouldn’t have (against Jacksonville in London, at New England, against Denver). And they have angered bettors.
Most notably, perhaps: Dave Portnoy, the Barstool Sports founder who proclaimed that he has “quit gambling” as a result of Buffalo’s three-point overtime loss at the Philadelphia Eagles, who went into the game as a 2.5-point favorite.
Buffalo Bills lead to (probably temporary) betting end for Barstool’s Dave Portnoy
Portnoy took his frustrations to X, formerly Twitter, after the Bills ultimately lost in Philadelphia despite carrying a 10-point lead into the fourth quarter.
The Barstool frontman claimed to have placed a “monster bet” on the Bills. After the visitors suffered their third loss in four games, Portnoy called it quits. Again. It marks at least the third time he will walk away from the gambling game, posting: “I quit gambling. F–k Buffalo.”
But he didn’t go away quietly. Not without taking a few jabs at the officiating and NFL Commissioner Roger Goodell.
While he did not disclose the size of his “monster bet,” Portnoy, a self-described “degenerate gambler,” alluded to the football gods playing against him and his Buffalo Bills betting.
Jake Elliott booted a 59-yard, game-tying field goal with 20 seconds left in regulation. While Portnoy did compliment the “unreal kick,” he insisted that the “[only] reson that went in is cause I got a monster bet on the Bills.”
Gambling not treating Portnoy well
Portnoy has not had the best of betting runs of late. At one point, he placed a $10,000 bet on Notre Dame quarterback Sam Hartman to win the Heisman Trophy.
Heading into Week 2, Hartman held +2000 odds to win the coveted award, tied for fifth-best. They climbed to +900 two weeks later but only dropped from there: to +1600 in Week 6, +5000 the following week and ultimately +10000 and off the board.
Portnoy also lost a $120,000 bet on the Cincinnati Bengals before they lost to the Baltimore Ravens in Week 11. The NFL opened an investigation after that game looking into if the Bengals withheld information regarding an injury to QB Joe Burrow. Portnoy threatened to file a class action lawsuit against the Bengals and the NFL.
According to the New York Times, Portnoy filed for bankruptcy in 2004 after losing $30,000 gambling, facing $59,000 in credit card debit and owing his lawyer father another $18,000. Portnoy’s father conceded that “anyone who says my son is exaggerating his gambling issues, I wish he was. He isn’t.”
Portnoy once had a shot at NY sports betting
At one point, it looked as if Barstool Sportsbook might have a chance at entering the New York sports betting landscape. The brand, then owned by PENN Entertainment, was among the bidders to offer legal online sports betting in the Empire State. Regulators, however, opted for another Super Bid that excluded Barstool.
Hope remained that Barstool would eventually get into New York, though Portnoy and PENN CEO Jay Snowden both claimed relief by being left out.
Over the summer, however, PENN bought out Portnoy for $1 while also 10-year, $1.5 billion partnership with ESPN to create ESPN Bet that would take the place of Barstool Sportsbook.
This all adds up to not a great sports betting year for Dave Portnoy.