Forget investing in stocks or playing the lottery – the real wild ride is in the world of sports betting. These aren't just stories of lucky people winning big but tales of incredible intuition, nerves of steel, and sometimes a whole lot of crazy luck! Let me introduce you to the 20 biggest sports bet wins ever.
Before his legal troubles, Billy Walters was basically the king of sports betting. He was so notorious that bookies were terrified to take his bets. One of his most legendary wins was $3.5 million on the New Orleans Saints winning the 2010 Super Bowl – that's when they were the underdogs, mind you.
The actual amount he walked away with is a mystery, but let's just say it probably makes my annual salary look like pocket change.
Vegas Dave (aka Dave Oancea) isn't afraid to go big. This guy once dropped $20,000 on Holly Holm to beat Ronda Rousey, an upset for the ages. He pocketed a sweet $200,000. Then, in a legendary move, he bet $140,000 on the Kansas City Royals to win it all... when the odds were 30/1. Talk about nerves of steel! Naturally, he walked away with a cool $2.5 million. Guess even a seasoned gambler like me could learn a thing or two.
An anonymous bettor in the UK got incredibly lucky with a horse racing bet known as the Jackpot. This requires picking the winner of six consecutive races – a feat so difficult even seasoned horse enthusiasts would scoff. Against all odds, this bettor did the impossible and was the only person to get all six picks correct. The result? A jaw-dropping £1.5 million payout (about $2.07 million) would make me want to retire on the spot.
Drake has a... shall we say, mixed track record with sports betting. But in January 2023, he took a big swing, betting $916,147 on the Kansas City Chiefs to beat the Cincinnati Bengals. It turns out that sometimes celebrity bets pay off! With odds of 13/15, Drake walked away with a hefty (and some would say risky!) win of over $1.7 million.
This 61-year-old heating engineer got a free ticket to the races and decided to drop a whole £2 on a six-horse accumulator. That's the kind of bet where you need every single pick to win. One of those horses hadn't won a major race in 28 outings! You've got to respect the boldness. That boldness (and, let's be honest, a truckload of luck) turned into £1.5 million for Steve.
Tiger Woods hadn't won a major championship in a long, long time... like 11 years long. But James Adducci believed. So, this brave soul put down $85,000 on Woods to win the 2019 Masters. Talk about a gamble! Now, I'm a fan of a good underdog story, but I might've even hesitated about that one. Naturally, Tiger pulled off a legendary comeback, and Adducci walked away $1.2 million richer.
Fred Craggs, a fertilizer salesman, strolled into his bookie with a 50-pence accumulator bet (that's multiple bets rolled into one). He had a hunch about horses halfway around the world. And guess what? He nailed it! If only I were so lucky on my measly football bets. Craggs turned that tiny bet into a whopping £1 million. Not bad at all, eh?
Sometimes you just gotta believe in yourself... or in your horse. Mike Futter gambled on his racehorse, Monty's Pass, in a big way. Through a series of bets, he turned his faith in his horse into a life-changing payday. First, he scooped up £348,000 as the owner of the winning horse, then a cool £400,000 more thanks to his lucky bets.
Turns out, Sir Charles isn't just a basketball star but also has some serious betting chops. He boldly predicted that the New England Patriots – 14-point underdogs at the time – would win the 2002 Super Bowl. Okay, maybe I should try betting against the teams Charles picks... Anyways, his $500,000 bet paid off with a sweet $800,000 return.
In 2000, an incredibly lucky (and anonymous) bettor placed a €1 accumulator bet on Liverpool beating Chelsea. Not that impressive, right? Hold on a minute. For them to win, they needed Liverpool to score a late goal and overturn Chelsea's lead. With odds at 683,738-1, this person must've had a lucky horseshoe in their pocket. Against all expectations, Liverpool DID score, handing the bettor a staggering €683,738 payout.
Back in 1996, Darren Yates placed a bet that would send his name into horse racing legend. He wagered £62 on jockey Frankie Dettori, winning all seven of his rides that day at Ascot. Known as the 'Magnificent Seven,' Frankie pulled off the impossible (with a little help from his horses, of course). Yates cashed out a sweet £550,000 – more than my house is worth, I bet.
Mick Gibbs sure knows how to make an entrance on this list twice! This roofer hit the betting jackpot the first time with a 15-leg accumulator bet at an incredible 1,666,666/1 odds. It turns out that he won another £500,000 on a 30 pence bet after Bayern Munich's goalkeeper made an epic penalty save that secured his victory. I guess his roofing job isn't looking so glamorous now, is it?
Pro golfer Phil Mickelson was far from a safe bet for the 2000/01 NFL Super Bowl. But that didn't stop one dedicated fan from taking a $20,000 punt on the Ravens – at decent odds of 22-1. Sometimes, those big bets on your favorite teams pay off in ways lottery tickets never will! As the Ravens won, our lucky bettor became $440,000 richer.
Professional poker players aren't usually known for their golfing prowess... or are they? It turns out that a group of pro poker players bet Erick Lindgren that he couldn't play four straight rounds of golf, carrying his own clubs, in the scorching Las Vegas heat – AND score under 100 on each round.
Spoiler: He nailed it. Lindgren pocketed $340,000 for proving them wrong, while I just get sunburned when I try to golf.
This one's a long-game win. Richard Hopkins had a hunch about this talented kid he saw go-karting – some guy named Lewis Hamilton. He placed a series of bets: £200 on Hamilton winning a Grand Prix before age 23, £100 on a World Championship by age 25, and another £50 on both happening. Fast-forward a decade, Hamilton was crowned Formula 1 champion, and Hopkins walked away with a cool £165,000.
This one is heartwarming and a little bit crazy. Peter Edwards, a loving grandfather, bet that his 15-year-old grandson, Harry Wilson, would one day play for Wales. Talk about long-term thinking! Lucky for him, he lived to see his grandson suit up for the national team and pocket £125,000 from that £50 bet. Wish I'd placed a bet on myself to be slightly less bad at fantasy football…
Tayla Polia only had one bet under her belt before pulling off a mind-boggling NFL 15-leg parlay. Now, I barely understand regular bets, let alone parlays with 15 picks! With odds stacked at 20,000-1, she turned a tiny $5 wager into enough cash to make me weep with jealousy – $105,000. Let's just say her betting career started way better than mine.
Nicholas Newlife bet on Roger Federer's future victories a whole decade before his seventh Wimbledon win. Sadly, he passed away before seeing his bet pay off. But here's the inspiring part – his winnings, £101,840 from a measly £1,520 bet, were generously donated to the charity Oxfam. Even in his absence, his bet made a difference.
Here's one for all the passionate football fans out there. Adrian Hayward, a die-hard Liverpool supporter, put £200 on Xabi Alonso scoring from his own half... at odds of 125-1. Now, that's the kind of bet only a true believer, or someone utterly insane, would make. Naturally, Alonso shocked everyone by scoring that long-range goal and securing Adrian a whopping £25,000 payday.
Here's a heartwarming one! Leicester City was the ultimate underdog in the 2016 English Premier League, starting at odds of 5,000-1. One super-optimistic, and possibly slightly insane, fan saw something no one else did and threw down £100 on his beloved team.
As Leicester defied all logic and marched toward victory, our brave fan cashed out his bet and pocketed an incredible £29,000! While he didn't get the full potential payout, sometimes cash in hand is better than a long-shot dream.
So, there you have it - 20 biggest sports bet wins ever. A glimpse into the world of sports betting where people like Billy Walters, Tayla Polia, and Fred Craggs turned bold bets and a bit of luck into fortunes. Maybe, just maybe, there's a little bit of that beting magic out there for the rest of us too. Now, if you'll excuse me, I think I'll start scanning the odds for some potential long shots...
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