June 18, 2024 2 min read


Fact-checked by Velimir Velichkov

Barstool’s Boss Portnoy Wins $1.6M on Celtics Parlay Bet with DraftKings

The exec and famous sports bettor took it to his personal X page to celebrate the win of a two-pick parlay wager

Barstool Sports’ boss and passionate bettor, Dave Portnoy, is recognized for his hefty wagers on major sports events. Earlier this year, the seasoned bettor was able to turn a $600,000 wager into a massive $2.76 million win after the UConn Huskies won against the Purdue Boilermakers. Sharing his excitement via X, formerly Twitter, Portnoy wrote at the time that this was the greatest bet of his life.

Now, another major sports event was able to bring a hefty win to Barstool’s boss. Monday marked the NBA Finals game where the Boston Celtics met the Dallas Mavericks. After a 106-88 Game 5 win against the Mavericks, the Celtics triumphed as the NBA Finals winner.

Undoubtedly, the game brought excitement for Celtics fans and especially for Portnoy who placed a two-pick parlay bet on the major competition. The parlay wager with DraftKings consisted of Celtics emerging as the Winner together with Scottie Scheffler being selected as the Outright Winner of the 2024 RBC Heritage tournament in April.

Barstool’s boss made the bet back on April 20, placing a total of $100,000. In light of the recent win of the Celtics, Portnoy secured a staggering $1.6 million from his parlay wager with DraftKings. He took it to his personal page on X to celebrate the win and wrote: “It’s not about the money but I’ll take the quick 1.6 milly.”

Many users online congratulated Portnoy on his latest million-dollar win. However, some criticized him, asking about recent bets he lost.

Celtics Triumph Results in a $500K Loss for Drake

Earlier this year, Portnoy highlighted a number of recent wins he secured from major sports events. In a recap posted earlier this month, Barstool’s boss wrote: “Guys I hate to be that guy but I have the Celtics for 1.1 million and the Oilers for another million. If both those teams win I will be up 7.5 million in 2024 and have won every big event this year. This run should be taught in history books.”

But while the Celtics brought success for some, others lost their wagers. This is the case for Drake, the famous songwriter and Canadian rapper.

Per media reports, Drake placed $500,000 in Bitcoin on the Mavericks to win the NBA Finals. Had the Mavs won the NBA Finals, Drake would’ve secured an estimated $1.38 million in Bitcoin from his wager. Sadly, the “Drake curse” struck again with the famous rapper losing his six-figure wager.


Jerome is a welcome new addition to the Gambling News team, bringing years of journalistic experience within the iGaming sector. His interest in the industry begun after he graduated from college where he played in regular local poker tournaments which eventually lead to exposure towards the growing popularity of online poker and casino rooms. Jerome now puts all the knowledge he's accrued to fuel his passion for journalism, providing our team with the latest scoops online.

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