8 Huge Wagers and Bets from History

The House always wins, right? Well, almost always. Betting isglamorized for the thrill and buzz they afford to the punter, as well as providing some remarkable stories of near-misses and could-have-beens. Once in a while, too, Lady Luck fortunes the brave and smiles upon his daring enterprises. Below are eight of the biggest bets in history; some are winners, some are losers; but all involve mindbogglingly high stakes.

  1. Matthew Webb – Niagara Swim ChallengeMatthew Webb

English Navy captain Matthew Webb became the first man to swim across the English Channel without the use of any artificial assistance back in 1875. Webb used the publicity gained from the feat to release a string of merchandise, including pottery and his own book. In 1883 he tried to capitalize upon his fame by setting himself up for life: he would make an audacious bet with the public and with fate. He wagered that he could swim across the foot of Niagara Falls; the stakes: $12,000 versus his own life. Such a fortune in today’s terms would equate to well over $300,000; however, unfortunately, this was a step too far and Webb tragically died after being dragged under by a whirlpool at the waterfalls’ base.

  1. Stu Ungar / Bob Stupak – 3 Pack Recall

Stu Ungar

Stu Ungar was widely regarded as one of the best blackjack, Texas Hold ‘Em and gin rummy players of all time, largely on account of his fantastic memory. Ungar was a three-time World Series of Poker champion and renowned for his ability to count cards and remember them without error. In 1977 this memory was put to the test by Bob Stupak, a casino owner and prodigious gambler himself. Stupak bet Ungar $100,000 that he could not remember the exact order of three decks of cards dealt at random. Remarkably, Ungar reeled off all 156 cards without a single mistake and pocketed the winnings.

  1. Ashley Revell – A Single Spin of the Wheel

Ashley Revell

Ashley Revell is not exactly a professional gambler; rather, he relied on one, massive score and then quietly took his winnings and exited the building. In April 2004, Revell sold everything he owned, scraped together his earnings (totaling $135,000) and staked it all on red. He even changed his name by deed poll to Ashley “Blue Square” Revell in order to receive donations to his pot from the betting syndicate. Remarkably, he won; but instead of placing further bets, he simply gave a $600 tip to the croupier and made off with the moolah. Six years later, the cast of American TV show The Buried Life would try a similar feat, betting $125,000 on a single spin on the wheel. They won; but got a bit greedy and staked it all a second time, only to lose everything. Quit when you’re ahead, guys!

  1. Anonymous – 13-bet Accumulator


In 2001, an English sports fan from Staffordshire bagged a cool £500,000 from a mere 30p bet after correctly predicting 13 different sporting outcomes. The finale of the bet came when Bayern München won the Champions League and bookmakers described the winnings as the “biggest football-related payout in memory”. Incredibly, the man had enjoyed similar luck two years previous when he won £157,000 from a 14-event accumulator worth just £2.50. Understandably, the man wished to remain anonymous. And they say the accumulator is a mug’s bet!

  1. Frankie Dettori’s Magnificent Seven

Frankie Dettori

Italian jockey Frankie Dettori is perhaps the most famous representative of his sport, and in 1996 he created history by winning all seven races at British Champions’ Day at Ascot. In doing so, he also defied odds of more than 25,000-1, spreading widespread heartbreak amongst the bookmaker brethren. Several punters profited from the Italian’s remarkable feat, amongst them joiner Darren Yeats, who, despite his wife’s protestations, put £67.58 on the races and collected a cool £550,000 in return. Unfortunately, not everyone was as lucky. A cleaner backed Dettori in each of the races with 50p; but only singly, meaning she won £19 as opposed to more than the £100,000 she would have won had she gone for the “mug’s bet”. Dettori himself was honored with a statue outsider of Ascot in recognition of his remarkable achievement.

  1. Kerry Packer: “Toss You For It”

Kerry Packer

Known as “The Big Fella” in betting circles, Australian tycoon Kerry Packer was no stranger to mammoth bets, having lost an incredible $7 million in a single unlucky day at Sydney’s Golden Slipper Stakes race tracks in 1987. But perhaps his most memorable bet was one that was never accepted. In the late 90s, Packer was playing roulette in Las Vegas and overheard a Texan tycoon complaining about low stakes. Packer inquired as to how much the Texan was worth, and, according to which story you hear, his response was anywhere between $50-100 million. Without batting an eyelid, Packer drawled, “Toss you for it,” – i.e the Texan’s fortune. Needless to say, the American went back to his game with his tail between his legs.

  1. Archie Karas – The Run

Archie Karas

The incredible life story of Greek-born card shark Archie Karas has more ups and downs and than a bouncy castle. According to Karas, he has gambled with higher stakes in his lifetime than anyone else in the world and ricocheted back and forth between being a millionaire and destitute several times before his famous run in Las Vegas. In 1992, he arrived in the betting capital with $50 in his pockets. After defeating many highly rated poker and pool players – among them Stu Ungar, the man with the incredible memory – Karas had racked up his fortune to an amazing $17 million in just six months. He turned to $100,000 single rolls of the die and by 1995, had amassed a whopping $40 million. Unfortunately, he lost it all in the same manner that very year and in 2013 he was arrested for cheating at the betting tables. He is currently facing charges of burglary, cheating and fraud.

  1. Floyd Mayweather – Miami Heat

Floyd Mayweather

Over the years, the highest paid athlete of 2012 has made some ludicrous bets, many of them involving his long-time friend 50-Cent. However, in June 2013, all of these paled in comparison when ‘May the Money’ staked an incredible $5.9 million on a single basketball game. Mayweather backed Miami Heat to beat the Indiana Pacers, which they did, 99-76. In the biggest bet in sports history, Mayweather doubled his money and reportedly had to lay out the wager across nine different bookmakers just to have it accepted. Between 2010 and 2012 Mayweather tweeted pictures of 46 winning betting slips, combining a total of $3,938,722 in winnings… Suspiciously, he never tweets a losing slip, however. You’re fooling no-one, Floyd!

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