5 Stories of the Luckiest Gamblers You’ll Ever Hear About

By | February 28, 2021

“It’s better to be lucky than good.” Sports bettors know this phrase is one of the few that is irrevocably true.

Gamblers who have seen their bankrolls grow and wither time and time again all would agree: They’d trade some of their skill for just a little bit of good fortune, that is if they had any real skill in the first place.

It’s hard to debate that the universe seems to have preferences toward rewarding some and punishing others. In this article, I’ll explain five bets by people who clearly did more than a little good in their past life and ended up with some impossibly lucky betting wins as a result.

1 – Lucky Number Seven

If you’ve ever spent time betting at a race track, you know that regardless of how good a horse a jockey team may be, winning seven races in a single day is simply unheard of success. Even one of the sport’s legends, Italian jockey Frankie Dettori could never be expected to pull of such a feat.

On September 28, 1996, the aforementioned horseman was scheduled to run seven races at England’s famed Ascot racetrack. Optimistically, and trying to come off as a reasonably humble individual, Dettori said during pre-race interviews that he thought he’d only be able to finish the day with one or two wins under his belt. He couldn’t have been more wrong.

Perhaps Dettori could have used the same confidence that bettor Darren Yates showed in the five-foot-four-inch Italian. Although not willing to risk an exorbitant amount of money, Yates made a wager that would change his life forever.

Prior to race number one, Yates bet 67 British pounds (GBP), or roughly $90 USD on Dettori to win all seven events. If he lost one, the bet was a loss. But if by some miracle he was able to pull off the feat, Dettori would make Yates a rich man, which was especially important because Yates had a carpentry business which was struggling heavily at the time.

In the end, Dettori came through and wound up finishing in the top spot in all seven of the day’s races. Although the real winner of the day was clearly Darren Yates. He took home more than 550,000 GBP, or roughly $764,000 USD. How’s that for a day at the track?

2 – Raising the Roof

Mick Gibbs was a simple roofer hailing from Staffordshire, England. But he would quickly be known as the luckiest man in town.

After finding 30 pence (the equivalent to about 40 cents in the US), presumably in his couch cushions, he decided the best use of that money was a longshot bet that would have one asking, “Wouldn’t you just be better off buying a lottery ticket?”

With odds of 1,666,666 to 1, you could argue that a lottery ticket would have had a higher chance of hitting than an incredible 15-leg parlay.

Playing the Lottery

It would be plenty exciting to simply say that Mr. Gibbs hit on all his bets, but that wouldn’t quite portray the drama that unfolded on the field. His first 14 picks had already hit when Valencia faced off against Bayern Munich. Gibbs needed Bayern to win in order to complete the unlikeliest of bets.

The teams on the field made Gibbs sweat it out. The match would eventually come down to penalty kicks. When the dust settled, the roofer from Staffordshire took home 500,000 GBP, or roughly $700k USD.

When you talk about return on investment, turning 30 pence into 500,000 pounds is about as good as anyone could ever hope for.

3 – Let It Ride

Europeans, as far as I know, don’t have a huge affinity for Major League Baseball. Heck, a good deal of American sports fans don’t watch with regularity—let alone bet millions of dollars on the games.

A European man, known only by “Sir Ride a Lot,” visited Las Vegas in 2017 in order to bet on the Fall Classic between the Dodgers and the Astros. The series would go seven games, but the excitement happening on the field was trumped by the action taking place inside the sportsbook.

Our European gambler came out hot, winning the first five games of the series. Heading into game 6, he had won more than $6 million in profits already during the series.

Think he called it quits and headed back across the pond? Of course not.

Sir Ride a Lot decided to let fate take over (who could blame him at that point?) and throw the entire $6 million on the Dodgers in Game 6. I probably don’t need to tell you this, but he won that, too.

Following game 6’s massive win, he was staring at $14 million in profits. I wish I could end this story by saying he bet it all on the final game of the series, but alas, he called it a day. Perhaps $14 million was just too much to risk, and at that point, wouldn’t it just feel a little precarious to test the gambling gods?

4 – An Unusual Donation

Charities do a lot of things, but refusing donations is not one of them. Perhaps that’s why in 2016, the Oxfam charity didn’t blink when a man who had recently passed away left them a betting slip, courtesy of his will.

The deceased was Nick Newlife (kind of an ironic name, no?). Newlife had allegedly always regretted not betting on tennis deity Roger Federer to win his first Wimbledon championship back in 2003. With that in mind, he took out a bet shortly thereafter that he would win six more titles at Wimbledon before 2019; that’s six championships in 16 years for those keeping track at home.

He must have felt confident, because he was willing to bet 1,520 GBP, or roughly $2,000 USD, on his faith in Federer’s successful decade. The payout if Federer held up his end of the deal? A cool 101,840 GBP, or $141,000 USD.

Winning Money

Roger Federer defeated Andy Murray in 2012 for his sixth Wimbledon title, meaning Newlife had won the bet with room to spare. That’s the good news.

Unfortunately, Newlife died three years prior to seeing his miracle bet go from black to green. Still, this story has a happy ending. He left the betting slip to the Oxfam charity, an organization that works to fight global poverty. They collected his six-figure winnings which I can only assume went to good use.

5 – Crazy Eight

Fred Craggs of Yorkshire was in the fertilizer business before his life was forever altered by the luckiest 60th birthday present one could ever ask for.

To celebrate turning the big 6-0, Craggs decided to put down 50 pence (less than $1 USD) on an eight-horse parlay in 2008. This wasn’t one of those situations where he had spent hours at the track studying the horses and jockeys waiting for the perfect time to strike. Instead, he picked eight longshots, but who cares? He only bet a meager amount.

If you’re wondering how much of a longshot I’m talking about, try 2 million to 1 odds.

Of course you know how this story ends: Craggs won the bet, but the wrinkle in the tale is that he didn’t know it at the time. He realized he had hit the unlikely parlay when he walked into the local shop to place another bet.

Due to the accumulator, he should have been paid out 1.4 million GBP but the sportsbook he was playing at had a winnings cap of 1 million. I guess 400,000 GBP is 400,000, but after hitting a 2 million to 1 bet, it didn’t seem like the time to complain.

Craggs ended up taking the money and retiring from the fertilizer industry a few years early. There’s probably a joke in there somewhere.


Most bettors can only dream of the success that the gamblers in this article have enjoyed. Though these stories may instill some feelings of jealousy, they’re also a reminder that it only takes one lucky day to change your life for good.

Perhaps the problem is most reasonable people would never dream of making these longshot bets, but one saying begs to differ: You can’t win if you don’t play.

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