Dave Portnoy Wins $1.5 Million With Celtics Parlay at DraftKings

Barstool Sports founder Dave Portnoy won big at DraftKings with the Boston Celtics 2024 NBA Championship victory.

He placed a $100,000 parlay bet on April 20 that involved the Celtics winning the championship and Scottie Scheffler winning the RBC Heritage.  The odds were +1492 with the payout $1,592,500. 

“It’s not about the money but I’ll take the quick 1.6 milly," Portnoy tweeted.

Portnoy claims to have won $5.4 million betting parlays in 2024 thus far.  That total would reach $7.5 million if he won his latest two bets — but the Oilers trail the Panthers 3-1 in the Stanley Cup Final.

“This run should be taught in history books,” Portnoy wrote while boasting about his gambling streak.

It's not immediately clear if any losses have helped bring down that $5.4 million number.

Step Out of Your Comfort Zone and Become a Bookie https://t.co/KaI3zoBDmP via @YouTube

— gambling911 (@gambling911) July 22, 2023

Another of the big name celebrity gamblers, recording artist Drake, did not have much luck with his bet.  He lost $500,000 backing the Dallas Mavericks to win it all.  That bet was not placed at DraftKings, but Stake out of Canada.

Portnoy's Barstool Sports was previously linked to Penn Entertainment and rebranded as ESPN Bet.  Drake still acts as a celebrity representative for Stake.com.