In the last four months, Barstool Sports founder Dave Portnoy has cashed in on some long-term bets. The 47-year-old’s total is up to $5.4 million. Dave had bets on Michigan and Washington to both win their college football playoff semi-final games. It was a total of $1.5 million for him between those two games. 

Next, he had the future placed on the Kansas City Chiefs to win the Super Bowl. After Kansas City won their second-straight championship, Portnoy won another $500k. His winning streak was not over. He put his money where his mouth was and placed $600k on UConn men’s basketball to win the March Madness. When UConn won their second-straight title, Portnoy won a whopping $2.1 million.

Now, Dave has a bet placed on hockey. Over the weekend, Portnoy bet $150,000 on the Edmonton Oilers to win the Stanley Cup. Those are currently the third-lowest odds to win. Can Dave Portnoy keep his hot gambling streak alive and cash another futures ticket? 

Will the Edmonton Oilers win the Stanley Cup and cash another futures bet for Dave Portnoy?

Out of all teams in the Western Conference, the Edmonton Oilers have the best odds to win the Stanley Cup. Three of the four teams with the lowest odds to win are in the East. They are the Hurricanes, Panthers, and Rangers. That hasn’t stopped Barstool Sports’ Dave Portnoy from placing a bet on Edmonton to win it all. 

The Oilers are trying to snap a streak of not making the Stanley Cup Finals. Their last appearance was in 2005-06. Edmonton’s last title was in the ‘89-90 season. It’s been a while since the Oilers were holding the Stanley Cup. However, the team got over a huge hurdle last night in a 7-4 vs. the Kings. 

Edmonton was previously 0-7 in their last seven Game 1 appearances. Their last game one win before last night was in 2017 against Anaheim. The Oilers broke that un-wanted streak and are optimistic about their chances this postseason. So is Barstool Sports’ Dave Portnoy who placed $150,000 on Edmonton to win it all. If the Oilers do in fact with the Stanley Cup Finals, Portnoy would win $1.2 million. That would bring his total to $6.3 million in the last six months. 

Connor McDavid made playoff history last night for the Oilers. He became the 14th playoff to eber record five assists in a playoff game. The first since 1988. His teammate Zach Hyman had a hat trick for the Oilers and mentioned after the game that they need to continue to defend home ice. Additionally, Hyman said it’s a lot easier to play knowing you only need three wins after Game 1 and not four. The Stanley Cup Finals begin on June 3. We’ll have to wait and see if the Oilers can make a run and reach the Finals for the first team in nearly 20 years.