Dave Portnoy: Biggest Bets, Wins and Losses

Dave Portnoy Betting

Credit: Zach Catanzareti Flickr

You might not have heard of Barstool Sports, and that’s because it is a blog aimed at the American market first and foremost. Calling it a blog makes it sound a bit twee, but in reality it is a juggernaut of a website covering all the sporting action in the US and beyond, with up to the minute articles, audio, and videos.

Dave Portnoy is the man who founded Barstool Sports, and as a result, he has a fair bit of money to play with. One of the things he likes to do with some of that money, is to bet, and bet big.

He uses his deep knowledge of sports to make high bets odds at short odds, usually on strong favourites, but he places his wagers early enough that there is still value in the short odds. He also chooses markets such as competition winner in golf, or a team to win the men’s NCAA basketball tournament, so the number of other options means the odds can’t shorten too much until later on in the competition.

As a bettor, he really came to wider attention in 2024, when he made a series of successful bets on American sports during the period of January – April, hitting the headlines seemingly every week for winning seven figure sums.

It probably helped that he consistently published his bet receipts on X/Twitter, along with running commentaries, to the delight of his 3 million+ followers.

He hasn’t always been s successful with his betting though.

In 2004 he filed for bankruptcy, and in his earlier days his gambling debts left him owing his father $18,000 after he stepped in to help Dave out. In November 2023 he lost $120,000 betting on the NFL, and it wasn’t the only time he has lost 6 figure sums while gambling, so while he’s doing alright now, it could have easily gone the other way.

Dave Portnoy's Biggest Bets

Rosebowl Victory for Michigan Wins $1 Million Bet for Portnoy

Bet: $1,000,000 (£798,490) - Michigan to Win the Rose Bowl - Won

Portnoy had 'retired from betting' before placing this bet, and announced on social media that he was so confident that Michigan would beat Alabama in the Rose Bowl, that he was coming out of retirement and betting $1 million on the result.

It was a great game, and a close game, with Michigan finally putting it to bed in overtime, and the win kicked off an incredible streak of good luck for Dave Portnoy, who won even larger amounts several times in the following few months.

Dave Portnoy $600,000 Huskies NCAA Bet Wins $2.76 Million

Bet: $600,000 (£487,074) - UConn Huskies to Win NCAA - Won

This was Dave Portnoy's biggest and most successful ever bet. It was a massive $600,000 wager that the University of Connecticut Huskies would win the NCAA basketball tournament.

What's more, his levels of confidence throughout the competition never waned. The Huskies were the defending champions and there was a strong chance that they would do the business again, so the odds of 18/5 that Portnoy secured through DraftKings were good value.

As always, he placed the bet just before the competition began, and watched as UConn dominated every game they played, including the final which they won with points to spare.

Dave Portnoy Blames $500k Losing Bet on a Jinx

Bet: $500,000 (£400,245) - Virginia Tech to Win - Lost

At the time, the $500k Dave Portnoy bet on Virginia Tech equalled the most he had ever wagered in his life, it was he joint biggest stake. It would also be his biggest ever loss, as Virginia Tech never got close to winning the game.

Incredibly, Portnoy blamed his loss on a 'jinx' among his friends, who changed the 'energy' in the room. This is a common fallacy among gamblers, but most people - especially those wagering huge stakes - understand that.

Dave Portnoy Doubles $500k Bet As Kansas Chiefs Win Super Bowl

Bet: $500,000 (£399,475) - Kansas City Chiefs to Win Super Bowl - Won

Never bet against Mahomes. That was the advice Portnoy gave after winning his $500k bet on the Kansas City Chiefs beating the San Francisco 49ers in the Super Bowl LVIII.

This huge bet was part of his incredible winning streak at the start of 2024, and it was one of the smaller ones if you can believe that. He also bet $10,000 on the result of the coin toss at the start of the game, which he lost, but I don't imagine he was too miffed considering the 7 figures he won from his main bet.

It must have been a tough watch though, as the Chiefs were literally seconds away from disaster at the end of the game.

$1.65 Million Win for Dave Portnoy After Scottie Scheffler Masters Victory

Bet: $300,000 (£243,258) - Scottie Scheffler to Win The Masters - Won

Coming just days after winning $2.76 million on the NCAA basketball tournament, Portnoy's bet on Scottie Scheffler would earn him another $1.65 million to top up his pot.

Scheffler was the world number one, so it wasn't the riskiest of bets, but his performance at the 2024 Masters was up and down to put it lightly. He kept saving himself though, not to mention Dave Portnoy's $300,000 stake.

The bet had been placed just before the competition began, so the odds of 9/2 look pretty good in hindsight. Had he waited until part way through the competition, those odds would have been slashed to eliminate all value.