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5 Best Super Bowl Bets Ever Made

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Best SB Bets Title Photo

As Krusty the Clown’s financial guy explained on The Simpsons, “gambling is the finest thing a person can do – if he’s good at it.” The Super Bowl tends to be the biggest sports betting event in the United States and Canada, with millions of people looking to make a quick profit by showing off their ability to predict football. As a result, Super Bowl odds and props are among the most popular plays on an annual basis.

With Super Bowl LI around the corner, the sports betting world once again turns their attention to the NFL. Experts will pour over trends, statistics and franchise history in an attempt to discover an inside edge. However, it isn’t experts who always win big. The following five Super Bowl bets are among the best ever made, including sharp action by musicians, Vegas legends and even a random dude who decided to place a grand on the least likely outcome at the beginning of a championship game.

5. Random Punter Wins $50,000 On A Safety
Prop bets were dreamed up by genius Las Vegas bookmakers to pad their bottom line. A run of truly boring Super Bowls during the 1980s and 1990s lead to a reduction in wagering interest on the big game, so bookies needed to find another way to create betting entertainment for customers. The first famous prop bet ended up being one of their most expensive mistakes. When William “The Fridge” Perry rumbled into the end zone during Super Bowl XX, sportsbooks lost quite a bit of cash because they initially gave odds as high as 75-1 on Perry scoring a TD. In fact, the action was so furious on this prop bet that the odds eventually dropped to 2-1 before the kickoff.
Prop betting action has gained momentum since then, with sportsbooks becoming more sophisticated in their offerings. This didn’t deter a random punter from nailing one of the best prop bets in Super Bowl history. Jona Rechnitz wagered that the first score of Super Bowl XLVI would be a safety, betting $1,000 on 50-1 odds. He ended up collecting a $50,000 payout when Brady grounded the ball for a safety. Sure, some sportsbooks were offering 75-1 odds on the prop, but his $50,000 payout remains one of the best bets in Super Bowl history.

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4. Birdman Bets A Million On Green Bay
Flush with cash earned through a successful career in the music industry, Birdman spends quite a bit of his time and money growing his public reputation as a conspicuous consumer. In 2011, just before Super Bowl XLV, reports surfaced that he dropped a million-dollar wager on the Packers beating the Steelers along with a -3 spread. Apparently, part of the motivation was Lil Wayne, who’s a big fan of Green Bay. Shortly after the Packers win, Birdman tweeted “LETS GO PAINT THE TOWN RED… JUST CASHED IN A MILLI”, suggesting that he really did just win $1 million through his Super Bowl bet.
Amusingly, there’s a good chance that he made one of the worst Super Bowl bets in history the year after, when he stated that he was going to drop a $5 million bet on the Patriots against the New York Giants. There’s no word as to whether or not Birdman actually lost $5 million wager, although he claims that casinos wouldn’t touch his bet.

3. Bob Stupak Bets $1 Million On The 49ers
One of the true legends of Vegas, Bob Stupak fully embraced the high-risk, high-reward lifestyle of Nevada during the 1970s. He purchased, built and developed the betting establishment known as Vegas World, creating his own empire through smart promos that attracted vacationers and gambling fans around the world. In 1989, when Vegas World was pulling in revenues of more than $100 million a year, Stupak decided to show the world the right way to engage in high-stakes betting on the Super Bowl.
Super Bowl XXIII had the Cincinnati Bengals listed as seven point underdogs against the San Francisco 49ers, so Stupak took the points and ran with them, betting $1 million against the spread. By the end of the third quarter, the Bengals were ahead 13-6, and Bob was looking good. When Jim Breech nailed his third field goal to put Cincy up by three in the fourth, Stupak probably knew that his win was secured, giving him a chance to enjoy the finest final drive in Super Bowl history without worry. Incredibly, this kicked off a year in which he also won the World Series of Poker and the Super Bowl of Poker.

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2. Billy Walters Wagers $3.5 Million On The Underdog
Considered “the most feared man in the history of sports betting”, Billy Walters is as elusive as he is successful, building a sports betting empire through extensive connections. As one of the biggest sharks in the industry, he’s been rumored to have the ability to manipulate lines through strategic betting, increasing his profits whenever he has an inside tip. A 60 Minutes interview revealed that Vegas bookmakers avoid his action at all costs.

He must have spotted an opportunity when Super Bowl XLIV rolled around, because he dropped $3.5 million on the underdog Saints beating the spread. The Saints went ahead and demolished the Indianapolis Colts by a score of 31-17, and Walters collected a cool multi-million dollar payout to add to his already considerable wealth and prestige. Compare that to poker star Phil Ivey, who dropped $2 million on the same game, losing a wad of cash on the overwhelmed Colts.

1. 50 Cent Owns Birdman – Bets $1 Million On New York Giants
Music industry stars beef in different ways than regular people, throwing large money around to prove financial superiority. Before Super Bowl XLVI, Birdman challenged anyone to match his supposed $5 million bet on the New England Patriots, who were favored to win by a touchdown. During the previous Super Bowl, he reportedly won a million betting on Green Bay as favorites, so he felt pretty solid about his pick.

The only star to answer his challenge was 50 Cent, who was fresh off winning $500,000 by wagering on the Giants during the NFC championships. Surveying the situation, Curtis James Jackson III doubled his bet to $1 million, predicting that the Giants would beat the Super Bowl spread. Of course, the Giants would famously repeat their previous Super Bowl upset against the New England Patriots, so 50 Cent padded his NFL playoff total to $1.5 million.

Even more important, he won big while Birdman potentially lost $5 million. Perhaps one day, 50 Cent will end up changing his stage name to Cash Money Buckets.

More By Mark Solway

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