The gambling world is full of matched betting millionaire legends and myths. However, these ten professional sports bettors getting rich stories are entirely true.
Most gamblers who got rich from football betting generally have a background in Mathematics and spend considerable time in calculating and searching for the right offer for steady revenue. As such, they tend to be far removed from your average punter, who sees gambling as a simple pastime.
While not impossible, any bettor that wants to be a pro should first try one’s hand at sports punting and slowly learn the trade using smaller stakes, promotions and guidance from certified sources. We all start somewhere. However, where we end up will depend on constant effort and personal flair.
These are the most famous sports bettors that kept their dedication, made all the right steps and won big in the end.
1) Matthew Benham
Matthew Benham Net Worth: $20 MillionMatthew “Moneyball” Benham is the poster child of the rags to riches stories. In short, Matthew Benham gave up on a cosy Bank of America job to get rich from football betting and gain ownership of his favourite football club.
An Academic PastMatthew Benham graduated from the University of Oxford in 1989 with a physics degree. He then worked in finance and even earned the title of vice president of Bank of America.
How He Got Rich from Football BettingIn 2001, Matthew Benham switched fields, leaving the finance sector in favour of analytics. He joined Premier Bet, a sports staking company, where he developed predictive models, using his knowledge and previous experience in finance.
He started learning the trade under Tony Bloom, another famous example of people that got rich from football betting. Unfortunately, the partnership did not last, as 2003 saw Matthew Benham leaving the firm following a fallout with his mentor.
However, the decision seems to have been the correct one, as only one year later, he became a matched betting millionaire, even going on to open his own sports betting syndicate, Smartodds.
His Love for Football Did Not End ThereMatthew Benham has been a lifelong diehard fan of the West London Brentford FC. The club was facing considerable financial difficulties in 2007. The famous football gambler came in and provided a $700.000 loan for the fans to purchase the club. However, if the same fans declined the loan payment, Matthew Benham would take over ownership of Brentford.
And so, it happened. The fans failed to pay, and he became the owner of his favourite club in 2012. However, the skills that allowed him to get rich from sports betting further permitted him to slowly but steadily enhance the team’s worth and performance. Another happy ending, Brentford FC is now in Premier League.
2) Tony Bloom
Current Tony Bloom Net Worth: $1.3 BillionThe Brighton-born Tony “Lizard” Bloom is one of the most successful professional sports bettors. Nowadays, he preoccupies himself with entrepreneurship and the running of Premier League club Brighton & Hove Albion, as well as the Belgian First Division A team Royale Union Saint-Gilloise.
How He Got Rich with Sports Betting & PokerHis story starts quite aggravatingly with a teen Tony Bloom using a fake ID to place bets on horseracing events.
Naturally, it was not sheer luck that propelled him. Tony Bloom held a graduate degree in Mathematics from the University of Manchester. Just like many other maths grads who got rich via sports betting, like Dave Walsh and Zeljko Ranogajec, Tony Bloom put his Maths knowledge in service of punting.
Poker Earned Him the NicknameTony Bloom became The Lizard due to his coldblooded playstyle at poker tables. Legend has it that he won £2 million while allegedly playing for fun.
And poker remained his main source of income in the early days. As an event participant, he won the first prize in the Australasian Poker Championship, NO Limit Hold’em VC Poker Cup final in London, and scored fourth place in the 2005 World Series of Poker Tournament of Champions.
Later YearsTony Bloom might have gotten rich from sports betting and live poker. Still, his later years proved a lot calmer.
Bloom later went on to become an entrepreneur in the gambling and property investing sectors and be at the helm of two football clubs.
He also spends some of his matched betting billionaire cash on good causes. His Bloom Foundation covered the costs for developing a synagogue project in Hove.
3) Bill Benter
Bill Benter Net Worth: $1 BillionBill Benter is a Pennsylvania-born professional sports gambler who got rich from horseracing betting and punting on other sports events.
Another Mathematician Who Got Rich from Sports BettingBill Benter obtained a physics degree in 1977. His first feat in the world of pro gambling was with blackjack in Las Vegas, where he indulged in card counting.
However, his meeting with Alan Woods shifted his interest towards sports punting. The two became professional sports bettors and moved in 1984 to Hing Kong. The two devised a statistical model for choosing the winner in various sports events. He also worked with professional sports gambler Robert Moore.
Pro Gambler and PhilanthropistBill Benter has contributed to various charities and political groups. He was a donor to Barack Obama’s presidential campaign and the Democratic Party of Virginia. His trust additionally donated to Rabbis for Human Rights and J Street. Lastly, Bill Benter is credited with donating $1 million to the University of Pittsburgh.
4) Haralabos Voulgaris
Haralabos Voulgaris Net Worth: $500.000 – $2 MillionHaralabos Voulgaris made a name and fortune for himself by punting on various sports events, especially the NBA. His approach highly differed from that of more Maths inclined football bettors.
How He Got RichThe Greek Canadian Bob Voulgaris started punting on sports, and mainly on NBA events, in the late 90s. By 2000, he amassed a fortune and felt confident enough to place $1 million bets during a single day.
His nick was observing the game-management tendencies of several head coaches. Bob Voulgaris was also a poker enthusiast, earning over $3.000 million in live tournaments over 14 years.
Dallas Mavericks Recognised His TalentOn the 4th of October 2018, the Dallas Mavericks hired Bob Voulgaris as quantitative research and development director. His activity there ended on the 16th of June 2021 due to front office conflicts.
5) William Walters
Billy Walters Net Worth: $200 MillionWilliam Walters is an American entrepreneur who got rich from sports events betting. He also gets the privilege of being considered one of the most successful professional sports bettors in Las Vegas, keeping a winning streak for over 30 years.
Early Days and Business SuccessBilly Walters was born in Kentucky to an auto mechanic and an alcoholic mother. His father would die when young Billy was only 18 months old. The boy ended up being raised by his grandmother. However, his grandma would meet her demise when Billy Walters was only 13 years old.
He moved to Louisville and worked two jobs. In 1965, William Walters worked as a car salesman, selling an average of 32 cars a month. He showed an impressive work ethic, working 80 hours a week. However, at the same time, Billy Walters started participating in sports betting.
His Professional Sports Gambler CareerWilliam Walters left the automotive industry to fully dedicate himself to punting in 1981. In 1982 he pled guilty to a misdemeanour charge of possession of gambling records in Kentucky. But Billy Walters had a way of falling upwards. Soon, he decided to move with his family to Las Vegas.
There is where he earned his fortune with sports betting. During the 80s, William Walters joined the Computer Group, which utilised computer analyses for sports punting outcomes. The professional sports gambler went on to have only one losing year in 39 years and allegedly make between $50 and $60 million in a good year.
Unfortunately, Billy Walters was found guilty of insider trading with Dean Foods stock and sentenced to 5 years of imprisonment and a $10 million fine.
6) James Holzhauer
James Holzhauer Net Worth: $2 MillionJames “Jeopardy” Holzhauer is best known for his 32-year-long winning streak in the game show that gave him his nickname.
However, his lesser-known feat is how he made a fortune betting on sports events. He also proved a moderately proficient poker player, debuting in the World Series of Poker 2019.
However, he became a professional sports gambler in 2018, when he moved to Last Vegas, following his college graduation.
His main areas of activity were baseball, NFP, and college basketball. He states to have created predictive models for his punting sports. Holzhauer’s mainly participated in in-game betting.
7) Zeljko Ranogajec
Zeljko Ranogajec Net Worth: $610 MillionZeljko Ranogajec is a businessman and professional sports gambler. He mostly activated in horseracing punting, blackjack and many other forms of advantage gambling.
Early LifeZeljko Ranogajec hails from a Croatian immigrant family and has studied Commerce and Law at the University of Tasmania.
He started with card counting at Wrest Point Casino. He also met Shelley Wilson, his future life and business partner, a full-time employee of the gambling enterprise.
Zeljko Ranogajec eventually transferred his studies to the University of NSW but later dropped his degree in favour of advantage gambling.
He Then Made It Big in Sports BettingRanogajec earned his pro gambling profits through blackjack, keno, horse racing and other sports punting.
His betting approach hinged on finding small margins and closing deals with bookmakers for significant rebates. These actions attracted some attention and allegations of illegality. However, a TabCorp representative stated that there was no proof of illegal activity following inspections.
Nowadays, the professional sports gambler resides in Europe, mainly the UK and Isle of Man, getting an appointment as a consultant to Newfield Limited.
Ranogajec is a co-founder of Colossus Bets.
8) David Walsh
David Walsh Net Worth: $200 MillionHere is another story about how to get rich from football betting from down under. David Walsh is one of the best performing professional sports bettors, winning a staggering $17 million on the 2019 Melbourne Cup.
He Founded MONA With His WinningsDavid Walsh used his payroll from sports betting to fund and develop the Museum of Old and New Art in Hobart.
The process came with unexpected and considerable expenses, with Walsh stating that before the 2009 event, he was accruing bills amounting to $5 million a month. Luckily for the project, his success during the Melbourne Cup covered the costs.
9) Alan Woods
Alan Woods Net Worth: $670 MillionGambler and Mathematician Alan Woods was one of the biggest sports betting millionaires. Woods focused on blackjack and horseracing, working with Bill Benter and Zeljko Ranogajec in Australia and Hong Kong.
The Career of a Punting LegendLike most mathematically minded pro gamblers, his earliest success was managed by card counting techniques in blackjack.
Alan Woods did not dedicate his attention seriously to professional punting until his wife left him in 1979. This event triggered something in Woods’ mind. He went on to win $16.000 within four months through blackjack.
Alan Woods worked on a mathematical punting model for horseracing betting with Bob Moore and Bill Benter. Further so, he won millions from punting in collaboration with Ranogajec, whom he considered to be a rival.
Alan Woods passed away on the 25th of 2008 due to appendiceal cancer.
10) Robert Moore
Bob Moore Net Worth: $200 MillionNew Zealand has given some of the best stories for gamblers that made a fortune from horseraces betting and other punting activities.
From Rags to RichesIn 1983, Bob Moore arrived in Hong Kong with only AU$5 on him. He started working with Alans Woods and later Benter.
Moore would wager up to $2 million a day during his heyday and receive an annual return of 38%.
In a funny twist, while Moore started his staking career with Woods, he would leave him for working with Benter, whose system was considerably better. However, Bob would later turn once more and attempt to sell Benter’s data to Moore.
A Controversial FigureWhile he got incredibly rich with sports betting, his antics cost him considerably. He allegedly either bought a bar from a Chinese owner because he was made to wait for a pool table or threatened to purchase the restaurant beneath it and open his own bar with three pool tables.
His story has a sad end, however. Robert Moore committed suicide on the 18th of October 1997 by overdosing on sleeping pills.
This is perhaps a highlight of how gamblers can have unaddressed psychological problems even when on the upswing.
Extra Entry: Simon McMillanThis instance is perhaps the most important story of a gambler who got rich from football betting in the UK. His earnings attracted the attention of the HMRC and created a legal precedent from gambling taxation policies.
How Simon McMillan got Rich from Football BettingMcMillan utilised various mathematical systems to punt on British and European football matches and play poker. His approach would guarantee steady returns for his activity.
As such, gambling and football betting were his sole sources of income between 1998 and 2010.
The HMRC Took NoteHer Majesty’s Revenue and Customs issued a legal case against Ian McMillan regarding taxes on his income. It contended that the professional sports gambler engaged in trade and, as such was subject to income taxation on his punting revenue.
However, Ian McMillan successfully proved in court how he got rich from football betting. More so, he has shown that all income indeed originated solely from punting and poker. Since gambling activities are exempt from taxation in the UK, so was his revenue.
A Legal PrecedentMore than a staggering sum or an inspiring tale, how McMillan got rich from football betting provides a precedent for rulings regarding high-earning football bettors.
The court decision effectively deems punting to be tax-exempt within the UK, despite several sports betting millionaires making their fortune out of it.