A handful of people have made serious fortunes from betting. They are the exception, not the template: almost every name below won through a structural edge (a model, a pricing flaw, a rebate deal, information) plus disciplined staking, and several also built businesses around it.
This series profiles ten of them. Wealth figures are press estimates from when each profile was written (mostly 2019–2021) and should be read as such. If you want the realistic version of making a living from betting, start with value betting and bankroll management rather than the headlines.
ARTICLE 1: TONY ‘LIZARD’ BLOOM
Arguably the UK’s most notorious sports bettor, Tony Bloom, is the owner of Starlizard, a company that describes itself as a betting consultancy.
Starlizard has been reported to advise Bloom’s betting syndicate, which press accounts say can have seven-figure sums riding on a single football match.
It is widely described as one of the biggest betting operations in Britain; profit estimates in the press run as high as £100 million a year, but none are public. Bloom also owns Premier League club Brighton & Hove Albion.
Read more here.
ARTICLE 2: MATTHEW ‘MONEYBALL’ BENHAM
Although Matthew Benham has stated he dislikes the comparison between himself and the movie ‘Moneyball’, let’s be honest, he’s about as close as it gets!
Benham built his fortune through professional betting and his analytics firm Smartodds, then applied the same data-led approach to football as owner of Brentford (promoted to the Premier League in 2021) and FC Midtjylland.
Read more here.
ARTICLE 3: HARALABOS ‘BOB’ VOULGARIS
From the late 1990’s to the early 2000’s, Haralabos Voulgaris (a.k.a. Bob), made betting look easy, exploiting inaccurate odds on NBA points totals.
He has said he hit close to 70% on his best NBA angles for a stretch. That kind of strike rate came from a specific, temporary flaw, not from a repeatable system.
The flaw was in the bookmakers’ prices: first- and second-half totals were set as simply half of the full-game total, ignoring that scoring patterns differ between halves. He later worked for the Dallas Mavericks and went on to buy Spanish club CD Castellón.
Read more here.
ARTICLE 4: BILL BENTER
Bill Benter is one of only a few who has managed to master the world of betting on Horse Racing.
In the mid-1980s, Benter built a statistical model to beat the Hong Kong pari-mutuel pools. His winnings have been reported to approach $1 billion over the following decades.
His published work on combining a fundamental model with the public’s odds is still a reference point for anyone building a betting model.
Read more here.
ARTICLE 5: EDWARD THORP
Although he doesn’t fit the theme of a sports bettor, it would be rude not to include betting pioneer, Edward Thorp, in our article series.
Edward Thorp was made famous by his book Beat the Dealer, and by his own account casino staff once tried to harm him.
Thorp brought the phenomenon of card counting to light when his book was released in 1962, selling over 700,000 copies and making it onto the New York Times Bestsellers list.
Read more here.
ARTICLE 6: BILLY “THE GREAT WHITE SHARK” WALTERS
Billy Walters has been described by odds-makers in Nevada as a Great White Shark, the most dangerous and feared sports bettor in the world.
Over four decades, Walters is reported to have made hundreds of millions in betting profits, mostly on American football and basketball.
In 2017 he was convicted of insider trading (a stock case, not a betting one) and sentenced to five years. He was released to home confinement in 2020 and his sentence was commuted in January 2021.
Read more here.
ARTICLE 7: ZELJKO ‘THE JOKER’ RANOGAJEC
Zeljko Ranogajec is one of the most successful gamblers of our time, with a reported fortune built on casinos, horse racing and Keno jackpots.
Most people have never heard of ‘The Joker’. Much of his edge reportedly came from enormous turnover combined with rebates from tote operators, which made marginal bets profitable.
His turnover has been reported in the billions per year, and he is reported to have sent a betting exchange bankrupt (see the full profile).
Read more here.
ARTICLE 8: JEFF ‘21’ MA
Jeff Ma’s betting story is so good that it was adapted into the book Bringing Down the House and the movie, 21.
Ma was a member of the MIT Blackjack Team in the 1990s, which reportedly won millions from casinos through card counting.
He’s also renowned for his ability to stay cool under pressure, believing most people fail at betting because they let the emotions get the better of them.
Read more here.
ARTICLE 9: JAMES ‘JEOPARDY!’ HOLZHAUER
Outside Las Vegas sportsbooks, few people knew James Holzhauer before his 32-game winning streak on Jeopardy! in 2019.
He won about $2.46 million in regular play by applying betting principles, probabilities, aggressive sizing when ahead and expected value, to the game’s wagering decisions.
Before and after Jeopardy!, he has been a professional sports bettor.
Read more here.
ARTICLE 10: JONAS GJELSTAD
We couldn’t go through the whole series of 10 People Who Got Rich on Sports Betting without mentioning our own, Jonas Gjelstad.
Besides co-founding Trademate Sports, he has been a successful poker player and sports bettor, documented in his £10,000 to £1,000,000 in 12 months value betting run. That was a professional with a large bankroll, many accounts and full-time hours, not a typical result.
Read more here.
NOTABLE MENTION: ALAN WOODS
Alan Woods was an Australian actuary-turned-gambler who pioneered computer-modelled betting on Hong Kong horse racing, alongside Bill Benter.
Woods died in 2008. His estate was reported at around AUD 670 million at the time.
Read the full article here!
What the stories have in common
None of these people won by picking favourites. They found prices that were wrong, sized bets so a bad run couldn’t wipe them out, and kept going for years. Variance still applies at every level, and most bettors lose. If you want to bet the same way, start by learning to spot value bets and to size your stakes.
Real Trademate user journeys (results vary; past results are not a forecast):