Top 5 Craziest Sports Bets Of All Time

Top 5 Craziest Sports Bets Of All Time

All punters love to wax lyrical about their big wins and those crazy bets that somehow paid off. You can bet on some seriously crazy things but you’ll be going some to find any stories to beat these five; which we reckon are the five craziest sports bets of all time. 

Safety First: $75k Banked

Anyone who knows anything about the NFL, also knows that safeties aren’t that common. You can get pretty good odds, then, on a safety being the first score of an NFL game. Jona Rechnitz, a real estate owner in New York, took full advantage of that in 2012 by betting on a safety as the first score of that year’s Super Bowl. 

Rechnitz bet $1,000 at +5000 and so was the recipient of a cool $50,000 when Tom Brady was flagged for intentional grounding in the end zone, giving up – you’ve guessed it – a safety in the first quarter. 

Jona could have dined out on the story of that bet for the rest of his life, but instead chose to place the same wager – although for $500 – on Super Bowl XLVIII two years later in 2014. Remarkably, an errant snap on the first play of the game resulted in a Seattle Seahawks safety and a further $25,000 for the lucky Rechnitz.

Money Mayweather: +$600k

Boxer Floyd Mayweather Jr has certainly done plenty to earn the nickname ‘Money’. As well as earning an extraordinary amount of the green stuff through his career, Mayweather is also quick to flash the cash when the mood strikes. As well as plenty of big-ticket purchases, Mayweather is also well known for placing bets of extraordinary sizes.

Perhaps the best example comes from 2013, when Money’s money went down on the Miami Heat. The boxer was backing the team to win game seven of the NBA Championships against the Indiana Pacers and did so to the tune of a ridiculous $5.9 million!

The bet landed and saw Mayweather boost his bank account by a comparatively paltry (compared to his initial stake at least) $600,000. It was a wager, then, that could only possibly be placed by a punter with more cash than they know what to do with. 

All Hail the Fail Mary

The 2012 NFL clash between the Seattle Seahawks and the Green Bay Packers has become known by football fans as the ‘Fail Mary’. That’s because the game was ultimately decided in Seattle’s favor by a last play hail Mary touchdown which was simply dripping with controversy. 

With Russell Wilson’s pass in the air, receiver Golden Tate got away with a two-handed shove on corner Sam Shields before the two players simultaneously caught the ball. To the consternation of Packers fans and the confusion of most neutrals, the officials went ahead and awarded the touchdown. One man, however, was surely delighted at the call.

That man was Canadian, Gino DiFelice, who would have been watching the game far more closely than most. DiFelice had bet on a total of 15 NFL games and was waiting on only a Seahawks victory for his bet to pay off in full. The ‘Fail Mary’, then, allowed DiFelice to walk away with an astonishing $725,000 from a $5 bet.

A Saintly Win

Former pro poker player turned professional punter Billy Walters is well known in gambling circles for landing some pretty tasty wagers. Perhaps his most famous win, however, came as the result of a bet which he himself has subsequently admitted he staked too much on.

Going into the 2010 Super Bowl, the Drew Brees led New Orleans Saints were betting underdogs against the Indianapolis Colts. Walters, however, favored the Saints and my word did he put his money where his mouth was, by placing a bet worth $3.5 million.

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The Saints would go on to record a fairly comfortable 31-17 win to bring home their first ever Super Bowl and to help Walters bring home the bacon. It’s uncertain exactly how much Walters earned from the bet, but he has claimed to have got odds of around 100 which would have resulted in an astronomical payout if true. 

Cards on the Table

It’s not just pro punters like Billy Walters who can bring in the big bucks; sometimes an enthusiastic fan can be rewarded for the blind faith they show in their team. That was certainly the case for a devout St Louis Cardinals follower in 2011, who landed not one but two extraordinary baseball bets.

The 2011 Cards weren’t particularly well-fancied for success, but the anonymous fan who placed $250 on them to reach the World Series at odds of 50,000 clearly had other ideas. So confident was that fan, in fact, that they then doubled down and placed a further $125 at 99,900 that the team would win the whole thing.

Game after game went by and the Cards suddenly emerged as real contenders, reaching the postseason as the Wild Card team. The Phillies then fell to the Cards in the Division Series, the Brewers in the National League Championship Series and the Texas Rangers in the World Series. Cards fans across the land went wild celebrating their team’s unlikely victory, but surely none more so than the punter who netted a cool $375,000.                 

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Geoff Lambert

Geoff has been playing fantasy football since 1996 and covering it professionally since 2015. In addition to being the founder of GoingFor2.com and The Armchair Fantasy Show, Geoff has contributed to FantasyPros, FantasyLife, and the now-defunct RotoWriters, while also appearing on a multitude of fantasy podcasts. Geoff's favorite professional teams are the 49ers, the Pelicans and the Nationals.

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