Selecting the 7 most famous sports bettors wasn't easy, but we've managed to develop a tiebreaker. We didn't solely focus on celebrity status but also considered how significant their sports wagers were, as well as their success.

You’re up for an in-depth look into the unlikely gambling careers of 50 Cent and Floyd Mayweather, and you’ll discover some fascinating details about one of the most heated rivalries in the Premier League. Let’s cut straight to the chase!

1. Zeljko Ranogajec

Born in 1961 to Croatian immigrants in Australia, Zeljko Ranogajec is not well-known among amateur punters. However, with a net worth of over $600 million and a large share of it made by placing sports bets, he deservedly claims a spot among the prominent names in gambling.

His passion for gambling started with Blackjack. Having a degree in finance, his knack for crunching numbers and turning them into valuable hints is undoubted. Proof? His Blackjack card counting strategies got him banned out of several casinos. And that was just the beginning.

Zeljko then tried every other game on the casino floor, ending up with a passion for keno, and one of the largest keno jackpots ever won. The prize was worth well over $7 million, but he needed to wager almost $1 million per day for nearly a week to gain it. He turned to horseracing, which proved another fruitful avenue and used sports betting to further round his income.

If you plan on betting big like Zeljko, make sure you also consider the math behind your wagers!

2. 50 Cent

Curtis Jackson, aka 50 Cent, needs no introduction. Still, Curtis the punter certainly does, as many don't know him outside his musical career.

In a totally nonstrategic fashion, 50 Cent claims that his spectacular wagers are due to 'the voices in his head'. One such bet was on the New York Giants in 2012, earning him $500,000. The voices didn't stop, as he went all in, backing the Giants against an undefeated Patriots side at the Super Bowl to double his money. Surprisingly, he won that too.

But his most outrageous bet was a $1.6 million wager on Floyd Mayweather against Manny Pacquiao. We all know how that fight ended.

Something sets him apart from other high rollers on our list. In some of his lyrics and interviews, Jackson admits he has a gambling problem. It’s nice to know the voices didn’t take over completely.

3. Floyd Mayweather

The professional boxer is a controversial figure in the public sphere due to his arrogant antics. Still, this arrogance may have some backing if we consider that he retired with an unbeaten record. Did you know he’s a high-stakes sports bettor, too?

Indeed, his insanely vast wealth wasn’t built through betting, not even by a margin. However, Mayweather has won enough money through sports gambling to be included in our list. He might have lost a lot, too, with some reports claiming that he's lost over $50 million since 2017.

You might have seen him brag on social media with his winnings. For example, his 7-figure bet on a college football game in 2012 earning him over $1 million, or his most spectacular $5.9 million wager backing Miami Heat against the Pacers in the NBA.

Still, considering the rumours of him having a gambling problem, we will never know whether he’s ahead or not in his betting career. Little does that matter, though, when you sit on a $500 million wealth.

5. Anthony ‘the Lizard’ Bloom

Tony Bloom is arguably the wealthiest and most successful sports bettor in the UK. At the same time, he's as low key as they get, going to great lengths not to disclose his strategies. Still, we know he’s a fan of using data analytics to inform his betting decisions.

Bloom owns a betting consultancy company, Starlizard. Not all commoners can profit from his consultancy service, though. Starlizard only accepts customers with bankrolls worth £2 million up.

The Lizard is not only the godfather of sports betting but he's also amassed a decent share of his wealth playing at poker tournaments.

Passionate about football, a diehard fan of Brighton, and an entrepreneur at heart, he couldn’t stand seeing his favourites in the lower divisions. He took over the club in 2009 and invested more than £90 million to bring it to the Premier League.

Similarly, he took the Belgian football club Union Saint-Gilloise back to the top flight after more than 70 years. His data-driven approach seems to be working excellently, as the club currently stands at the top of the first-league table. Pretty impressive for a newly-promoted side.

Nobody knows exactly how much the Lizard is worth, but estimates indicate we’re talking a few billion.

5. Matthew Benham

Perfecting his strategies under Tony Bloom when the two partnered at Premier Bet, Matthew Benham went on to become one of the most successful punters in the UK through his efforts. Although the two now share a passionate rivalry, their courses in the gambling world are strikingly similar.

Both have used statistics to perfect their sports betting strategies. Both have amassed millions in the process, using the money to fund their childhood favourites.

After breaking away with Bloom and going solo, Matthew Benham started his own consultancy service, Smartodds.

He took over Brentford and applied Moneyball analytics to help them promote to the Premier League. Interestingly, Bloom’s Brighton and Benham’s Brentford met dozens of times on their way to the Premier League, deepening their rivalry on the football pitch.

Now that’s a story for the movies.

6. Ashton Kutcher

We all know Ashton Kutcher’s appearances in Two and a Half Men and the like. But you shouldn’t be misguided by the silly characters he’s played. Kutcher is a strategically-minded sports bettor who's amassed over $750,000 in four weeks on college football. Here, too, data was key to his success.

His sports betting winnings may well surpass this figure. In an interview, Kutcher admitted having placed bets for the US's largest betting syndicate. There's only one betting syndicate that significant in the country, and that's Billy Walters'.

Sportsbooks usually restrict gamblers who win too much. William Walters' syndicate fits this description perfectly, with average yearly profits averaging $15 million.

The syndicate’s idea to circumvent bookies’ restrictions is pure genius: let a seemingly dumb actor place the bets, and we’ll reap the rewards. However, it didn’t go on for too long. After his incredible four-week run, Kutcher was restricted too.

That didn't put an end to Kutcher's hot run in the gambling world. He went on to invest in an eSports betting company, Unikrn, which proved to be his most lucrative bet to date.

7. William Walters

We couldn’t let the most successful sports bettor, Billy Walters, out of our list. His reputation was somewhat tarnished by insider trading accusations leading to imprisonment. Former US President Donald Trump eventually granted Walters amnesty in his final day in charge of the White House.

Having started his gambling career at 9 years old, he's undoubtedly had enough time to perfect his betting system. Billy Walters’ betting tactics saw him earn over $50 million a month in his prime. He encountered a single losing year during his almost 40-year career, as the legend goes.

As with all other successful bettors in this list, Walters used data analysis to identify value and place large bets on the weakest lines.

But he didn’t do all the hard work by himself. He’s put together a team of programmers, mathematicians, and data experts to maintain his edge. Striving for the most accurate data proved key to his thriving.

Concluding remarks

Someone may object to our selections, asking why we didn’t include Michael Jordan or Wayne Rooney to the list. They’re nothing short of high-profile, and they’re also known for their betting habits. Point taken, but let’s face it. Michael Jordan is by no means an example. He’s lost $5 million at the Craps table and even went as far as placing bets on Rock, Paper and Scissors. Then you have Wayne Rooney, former gambling addict, who’s promoted a controversial bookie, accused of profiting off gambling addicts.

While 50 Cent’s ‘voices in the head’ and Mayweather’s hidden losses may not be educative either, at least they focused on sports.

On the other hand, passionate bettors will surely learn a thing or two from our article. The main takeaway? It’s all in the data!