Sports bettors are commonly told to stay away from parlays. These wagers are often called sucker bets, because they give sportsbooks such a large advantage.
Gamblers are also advised to avoid risking massive amounts of money on any single outcome. Nothing in sports betting is guaranteed, and one could easily lose their giant bet on a “sure thing.”
Nevertheless, sports bettors continue bucking common advice in order to make huge wagers and long-shot bets. And it makes for a great story when these gamblers are successful.
You can read nine such stories below, which involve people winning bets with either ridiculous odds or massive amounts of money on the line.
Fertilizer salesman Fred Craggs celebrated his 60th birthday by making an eight-horse parlay bet in 2008.
Craggs didn’t spend much time on the wager, especially since he selected eight long-shot horses. His hasty selections didn’t seem to matter much when considering that he was only risking 50 pence on the accumulator.
The odds of Craggs winning this bet were just 2 million to 1. But the unthinkable happened when each of his long-odds horses came through.
Craggs won the accumulator along with a £1 million payout. Interestingly enough, he didn’t even realize that he’d won until walking into the local William Hill shop to place more wagers.
The 60-year-old should’ve been in line for a £1.4 million payout based on his bet size and the odds. But William Hill had a rule in place that capped his winnings at £1 million.
Nevertheless, Craggs was a happy man when he revealed his big win to his family and retired with a much-larger nest egg.
Mick Gibbs placed what seemed like an impossible 15-team parlay bet in 2001. The roofer from Staffordshire, England wagered 30 pence that all 15 soccer (football) teams would win on his accumulator.
Staring at 1,666,666 to 1 odds of winning, Gibbs was essentially buying a lottery ticket. But his dream was close to reality after the first 14 parlay picks came through.
The final match came down to the Champions League game between Valencia and Bayern Munich. Gibbs needed Bayern to win in order for his accumulator to be successful.
As if there wasn’t already enough drama, the match went down to penalty kicks. Bayern Munich would prevail in the penalty shootout, and Gibbs won £500,000 after completing the 15-team accumulator.
Rory McIlroy is a highly successful golfer who has four Major titles and 14 total PGA tournament wins. He also spent 95 straight weeks as the world’s number one golfer.
But long before this, he was a teenager in Northern Ireland with an uncertain golf future.Gerry McIlroy always believed in his son, though, and made a bet to prove it.
Gerry and a few of his friends wagered a combined £200 that 15-year-old Rory would win the British Open within 10 years. He was given 500 to 1 odds on the unusual wager.
Rory won the 2014 British Open as a 24-year-old, which was within the 10-year parameter of the bet. Gerry received a £100,000 payout thanks to the victory while his friends split another £80,000.
In 2017, an Eastern European man traveled to Las Vegas to bet onWorld Series games between the L.A. Dodgers and Houston Astros.
This seesaw series went to seven games. And the man, who’s now known as “Sir Ride A Lot,” bet large amounts on the first six games.
Betting big on the World Series is nothing unusual. But what makes this story interesting is that the man let his winnings ride after every game.
Sir Ride A Lot built a $6 million profit after the first five games. Most gamblers would’ve been more than content with this amount and quit while they were ahead.
But Sir Ride A Lot did the unthinkable and put $6 million on the Dodgers winning Game 6 (-126 moneyline). He won yet again and added another $8 million to his bankroll, making for a total of $14 million.
He thought briefly about letting his winnings ride yet again on Game 7. But Sir Ride A Lot finally cashed out and took his massive profits.
After watching her husband make soccer accumulator bets throughout their marriage, a Kent, England housewife decided to do the same in the early 2010s.
After six years of placing parlay wagers, the woman got lucky and won a 12-team accumulator. She turned her small £1 bet into a massive £574,000 payout.
Afterward, the woman said that her previous record win was £25,000. And while this is impressive, it’s nothing compared to her current high.
Following the win, she couldn’t wait to treat her family to a “cracking Christmas.”
As for the lady’s strategy, there was none. She merely had her son read off the 12 matches and chose her favorite teams in each match.
Of course, there’s usually not much strategy involved with 12-team parlays anyways. Therefore, the woman’s gambler mindset shows that just anybody can win big with accumulators.
Charities are used to receiving all sorts of donations. But not many receive winning betting slips — especially one worth £101,840.
Nick Newlife had always regretted failing to bet on Roger Federer winning his first Wimbledon title in 2003. He decided not to miss out again and bet that the Swiss pro would win six more Wimbledons by 2019.
Newlife wagered £1,520 on this outcome for a potential payout of £101,840. His wager officially came through when Federer defeated Andy Murray to capture the 2012 Wimbledon title, marking Federer’s sixth win at the All England Club since the wager.
Sadly, Newlife passed away three years before seeing his miraculous betcome to fruition. He left the betting slip in his will to the Oxfam charity, which collected the six-figure prize.
All of the bets until this point have been about people either beating crazy odds or letting their winnings ride. But Billy Walters also belongs on this list for the sheer size of his biggest gambling win.
The professional sports bettor once wagered $3.5 million on the underdog New Orleans Saints beating the Indianapolis Colts in Super Bowl 44.
Walters is one of the most-astute bettors when it comes to handicapping games and making informed wagers. But even he admits that he got carried away by risking so much on a single game.
Lucky for him, the Saints cruised to an easy 31-17 victory and earned him a multimillion-dollar payout.
This was just one of many highlights in Walters’ illustrious gambling career. Unfortunately, he’s now serving prison time after being convicted of an inside trading scandal involving Dean Foods.
50 Cent, whose real name is Curtis Jackson, is a New York-born rapper and long-time Giants fan. Therefore, he couldn’t resist the urge to bet big on the NY Giants as they marched towards Super Bowl 46.
Jackson’s first placed a $500,000 wager on the G-Men beating the San Francisco 49ers in the 2011 NFC Championship. New York would prevail in a 20-17 overtime nail-biter.
This victory set the Giants up to play the New England Patriots in Super Bowl 46. Fellow rapper Birdman announced that he wanted to place a $5 million bet against anybody on the Pats’ ability to win the title.
50 Cent wasn’t prepared to risk $5 million. But he did offer to place a matching $1 million wager against Birdman.
The bet between 50 and Birdman didn’t happen. However, Jackson still went through with his $1 million bet and won when the Giants triumphed by a score of 21-17.
Winning seven horse races in a single day is a very difficult task, no matter how good the jockey and his horse. Franki Dettori, who’s one of the greatest jockeys of all time, was even a long shot to perform such a feat.
On September 28, 1996, Dettori was scheduled to compete in seven races at England’s Ascot racecourse. He said in an interview that he only thought it was possible for him to win 1-2 races that day.
While Dettori may have been skeptical, gambler Darren Yates wasn’t. He bet a combined £67.58 on Dettori’s ability to cross the finish line first in all seven events.
Yates was looking for a stroke of good luck, because his carpentry business was struggling. And he got this good fortune when Dettori won every single race.
Yates’ total winnings that day amounted to £550,823, which was likely more than enough to save his carpentry business.
Traditional sports betting strategy doesn’t advocate making risky bets. These wagers rarely come through and can slowly drain your bankroll.
But you can see that it’s sometimes possible to win risky wagers and net giant payouts.
The most-impressive win on this list is when Fred Craggs chose eight long-shot horses on an 8-play accumulator and won. He beat astronomical odds of 2,000,000 to 1 and earned £1 million as a result.
Mick Gibbs won a 15-team soccer parlay that was almost as impressive. Gibbs earned £500,000 after beating odds of 1,666,666 to 1.
Yet another big parlay win comes from a Kent woman who got lucky with a 12-team accumulator. Her £1 bet turned into a £574,278 payout after she was successful.
Of course, crazy sports gambling wins don’t always have to beat long odds. 50 Cent, Sir Ride A Lot, and Billy Walters all placed huge bets that earned them fortunes.
Sir Ride A Lot’s story is especially unique, because he didn’t stop after winning just one huge win. Instead, he continued letting his winnings ride until reaching $14 million.
In summary, I don’t recommend that you spend too much time attempting near-impossible sports betting feats. This is especially the case with huge bets and letting your winnings ride.
But if you have a little extra cash and are willing to take a lottery ticket, then the bigger parlays can be fun. You can win a massive amount with a small wager, just like some of the gamblers on this list did.
Save my name, email, and website in this browser for the next time I comment.
