Post Action Betting

Dave Portnoy makes Stanley Cup pick amid $5.4 million hot streak

Dave Portnoy’s Stanley Cup winner pick is in. 

The self-proclaimed hottest gambler on the planet is picking the Oilers to win it all in the NHL. 

Portnoy is looking to extend his unbelievable winning streak with a massive $150,000 wager on Connor McDavid and Co. to win the Cup this year at +700 odds on DraftKings Sportsbook. 

The bet would win him $1.2 million if the Oilers can win their first title of the McDavid era. 

Portnoy has won $5.4 million in 2024 on a handful of futures bets on some of the year’s biggest sporting events. 

The Barstool Sports founder 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 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. 

Connor McDavid #97 of the Edmonton Oilers skates up ice against the Arizona Coyotes at Mullett Arena on April 17, 2024 in Tempe, Arizona.
Connor McDavid looks on during an Oilers game against the Coyotes earlier in the season. NHLI via Getty Images

Earlier this month, Portnoy had a betting week for the ages, winning $2.1 million off of UConn’s national championship win and another $1.35 million a few days later thanks to Scottie Scheffler’s triumph at The Masters, bringing in a total of $3.45 million. 

“Guys I don’t think people realize what we are witnessing,” Portnoy wrote on X after Scheffler won the Green Jacket. “To come into #themasters as the world’s #1 and the hottest gambler on the planet. To have a bullseye on your forehead and still win with ease? We may never see a 4 month stretch like this again.  #eprestheallknowing”


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The Oilers are tied with the Panthers and Avalanche with the second-best Stanley Cup odds at DraftKings behind the Hurricanes (+650) in a wide-open title race. 

They will kick off their first-round series against the Los Angeles Kings at 10 p.m. Eastern in Edmonton on Monday.