Dave Portnoy’s Oilers bet, wild gambling hot streak still alive

Dave Portnoy’s unbelievable betting hot streak is riding on the Oilers.

The Barstool Sports founder placed a massive $150,000 wager in April on Edmonton to win the Stanley Cup at +700 odds on DraftKings Sportsbook.

The bet would win him $1.2 million if Connor McDavid and Co. can upset the Panthers in the Stanley Cup Final.

Portnoy has won $5.4 million in 2024 on a handful of futures bets on some of the year’s biggest sporting events, with another $2.5 million coming his way if the NHL and NBA championship rounds go his way. 

In addition to the Oilers bet, Portnoy also would win $1.6 million if the Celtics win the NBA Finals after wagering $100,000 on a two-leg parlay featuring Scottie Scheffler winning the Masters (+550) and the Celtics winning the NBA Finals (+145).

It’s been a ridiculous six-month stretch of betting for a man who once had to file bankruptcy for gambling losses.

Portnoy opened 2024 by winning a total of $1.5 million on New Year’s Day after the Michigan Wolverines beat the Alabama Crimson Tide and the Washington Huskies upset the Texas Longhorns to make the national championship game. 

In February, Portnoy won another half-million bucks when the Chiefs took down the 49ers in the Super Bowl. 

Two months later, he won $2.1 million off of UConn’s national championship win. He banked another $1.35 million just a few days later after Scheffler’s triumph at The Masters, bringing in a total of $3.45 million in less than a week.

Betting on the NHL?

The Oilers are currently +115 to win the series at DraftKings ahead of Game 1 on Saturday. 

The Celtics’ path to the title looks much easier after their Game 1 win over the Mavericks on Thursday. 

Boston is now a big -400 favorite to win the franchise’s 18th NBA title.