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crazy sports bets

Drake in a suit

Drake’s tragic betting slips resurface after Oilers lose Stanley Cup Final

The “Drake Curse” appears to be alive and well. Drake has been known to bet pretty large sums on sporting events whenever he gets a chance. The Toronto native has also developed a reputation for being notoriously bad at picking winners. …

Dave Portnoy on the phone

Dave Portnoy cashes $2.7 million sports betting ticket in ‘biggest win’ of his life

Barstool Sports founder Dave Portnoy on Monday pocketed a massive chunk of change thanks to what he called “the greatest bet of my life.” Portnoy backed UConn in their quest for back-to-back titles, and his faith in the Huskies netted him …

Sports bettor celebrates 14-leg parlay win worth nearly $500K thanks to a Christian McCaffrey touchdown

Sports bettor reacts after cashing nearly $500k on 14-leg NFL parlay

One NFL bettor was blessed with the Christmas gift of a lifetime Monday in the form of a winning parlay worth $489,383. San Francisco 49ers running back Christian McCaffrey played the role of Santa Claus. The 49ers star represented the final leg on …

A look inside a Las Vegas Sportsbook

1 wild NFL parlay cost FanDuel $20 million in Week 2

Not all bets are created equal. Some have long-shot odds that will never pay out. And some will cost a sports betting giant like FanDuel a cool $20 million. FanDuel promoted a +20000 field goal parlay last weekend. For the 200-to-1 parlay to pay out, …

streaker Super Bowl

Betting reporter calls b.s. on viral streaker story

A fan ran onto the field at Raymond James Stadium late in the fourth quarter of the Super Bowl on Sunday night, and there is now a rumor circulating that the fan turned the stunt into nearly $400,000. At least one former oddsmaker is not buying it. A …

Shorts guy Chris Matthew

Shorts Guy Chris Matthew gets to finally wear pants after Winnipeg wins Grey Cup

The Winnipeg Blue Bombers won the Grey Cup on Sunday for the first time since 1990, and nobody may have appreciated that win more than Chris Matthew. Matthew, a Blue Bombers fan, was anticipating a Grey Cup win by his team in 2001. He was expecting …

Nick Saban

Bettor risked more than $1,500 to win about $1 on Alabama

Alabama had what we would call a cupcake game against Louisiana-Lafayette on Saturday, and the end result was quite predictable. Nick Saban’s team may have left some gamblers disappointed, but one brazen bettor was more than happy to earn a …

LeSean McCoy Bills

LeSean McCoy bet $200K on Warriors to beat Cavs in Finals

The Golden State Warriors entered the NBA Finals as heavy favorites over the Cleveland Cavaliers, and one star NFL player is fully expecting Kevin Durant and the boys to take care of business. Buffalo Bills running back LeSean McCoy shared a photo of …

Bettor misses out on $100K with 15-team parlay as Patriots fail to cover by a point

A bettor who stood to win $100,000 on a 15-team parlay over the weekend ended up losing the $5 he risked when the New England Patriots failed to cover against the Baltimore Ravens on Monday night. Worse yet, the Pats fell just one point shy. …

Eli Manning Giants

Eli Manning cost bettor shot at winning $150K in eight-team parlay

The New York Giants had multiple chances to beat the Washington Redskins on Sunday, but Eli Manning single-handedly blew two of them. If you’re a fan of the G-Men who is angry with Eli at the moment, just be thankful he didn’t cost you a …

Gambler wins big on crazy Henrik Stenson, Aaron Baddeley parlay

Henrik Stenson was arguably the best golfer in the world to never win a major prior to his dominating performance at The Open Championship over the weekend. Betting on him to break through and end the drought would not have been all that insane. But …

Jason Pierre-Paul

Jason Pierre-Paul could play in Week 9 against Bucs

Jason Pierre-Paul finally signed a contract with the New York Giants last week, and the original plan was to get him up to speed so he can return following the team’s Week 11 bye later this month. On Monday, Tom Coughlin hinted that Pierre-Paul …

Bettor wins over $48,000 on $1 UFC parlay

Hardcore UFC fans who missed the live broadcast of UFC Fight Night 61 in Brazil on Sunday were likely stunned when they looked over the results. Antonio “Bigfoot” Silva and Edson Barboza were defeated on a night that was loaded with …

12 team parlay Tuscany

Bettor wins $45,000 on $15 12-team parlay

Was anyone rooting harder for the Atlanta Falcons on Monday night than the individual responsible for this parlay card? As Todd Furham shared on Twitter, one person won $44,985 after the Falcons covered the 12.5-point spread against the Green Bay …

Floyd Mayweather won over $600,000 on Geno Smith pick-six

The New York Jets looked like a lock to cover the spread against the Denver Broncos on Sunday, and then Geno Smith happened. The Broncos were favored by more than a touchdown everywhere and up to 9.5 points at some sportsbooks. With Denver leading by …

Colts’ collapse cost bettor $100K on 15-team parlay

The Indianapolis Colts led the Philadelphia Eagles 17-6 at halftime on Monday night and were up 14 points midway through the first quarter, but they just couldn’t hang on. The Eagles came soaring back to grab a 30-27 victory. They pried …

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