Dave Portnoy’s incredible betting streak hinges on the Oilers.
The Barstool Sports founder placed a massive $150,000 bet in April on Edmonton to win the Stanley Cup at +700 odds at DraftKings Sportsbook.
If Connor McDavid and company beat the Panthers in the Stanley Cup Finals, he’ll earn $1.2 million.
Portnoy has won $5.4 million in 2024 from futures bets on some of the biggest sporting events of the year, and stands to win another $2.5 million if he wins the NHL and NBA championship rounds.
In addition to his bet on the Oilers, Portnoy also placed a $100,000 bet on a two-leg parlay on Scottie Scheffler to win the Masters (+550) and the Celtics to win the NBA Finals (+145), which would earn him $1.6 million if the Celtics win the NBA Finals.
It was a hell of a six-month gamble for a guy who used to have to take chances. file for bankruptcy due to gambling losses.

Portnoy kicked off 2024 by receiving a combined $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 play in the national championship game.
In February, Portnoy won another $500,000 when the Chiefs beat the 49ers in the Super Bowl.
Two months later, he won $2.1 million when the University of Connecticut won the national championship, and just a few days later, Scheffler won $1.35 million when he won the Masters, giving him a total of $3.45 million in less than a week.
Do you bet on the NHL?
DraftKings currently has the Oilers at +115 odds to win the series ahead of Game 1 on Saturday.
The Celtics’ path to victory seems much easier after beating the Mavericks in Game 1 on Thursday.
Boston is currently the favorite to win the franchise’s 18th NBA title at -400 odds.





