The Biggest Basketball Betting Wins of All Time

Putting money down on basketball is something millions of people do for fun every week. While some are more competitive with it than others, few manage to take it to the heights these big ballers have. This is what you need to know about the biggest basketball betting winners of all time. 

Although all gamblers (should) know the house wins in the long run, some bettors do go against the odds and win spectacularly big. 

Whether that’s a world famous superstar putting down hundreds of thousands of dollars on their favorite NBA team, or an average punter putting down $5 on a speculative parlay for big returns, these are the stories of the people who beat the ‘books and won fortunes betting on basketball. 

March Madness Bettors Hit Big Parlays 

In 2021, one student from Colorado visited Las Vegas on vacation. While there put a $10 parlay on ten different March Madness results. And then promptly forgot about it. Two weeks later, that $10 bet turned into $35,000 after all 10 picks came through. Two of the picks were also Oregon State, who were big underdogs that year. 

The bettor later told the media he wasn’t an Oregon fan and had never even watched college basketball before. But he was considering getting a Beavers tattoo to commemorate his win.

Luckily, you don’t have to go all the way to Las Vegas to put a wager down on the basketball. Top online casino and sportsbook bet way is available 24/7, wherever you are, offering all kinds of basketball and other sports betting markets, alongside competitive odds and great bonus offers to get you started. 

One bettor who placed an online basketball wager in recent years turned $30K into $495,000. In the 2024 NCAA Men’s Basketball tournament second round, huge underdog Farleigh-Dickinson pulled off an upset victory over 1st seed Purdue – and one bettor had put down $33,000 on them to do so.

While $33,000 one one bet suggests the bettor wasn’t financially troubled before the bet, $495,000 is still a significant win in almost anyone’s books.

Floyd Mayweather’s $5 Million Miami Heat Wager

Outside of small parlay bets making a massive combined win, some people just like to bet big. For example, famous world champion boxer Floyd “Money” Mayweather. 

The big man lived up to his Money nickname in 2013 when he put down $5.9 million on the Miami Heat to beat the Indiana Pacers in that year’s NBA finals. The Heat, led by a prime LeBron James, won a close final match 99-76 to take the series and cool Mayweather’s sweat with a $6.8 million win. 

Three years later Mayweather was back to his high stakes gambling exploits. Before the 2016 season began, put $30,000 on the Golden State Warriors to win the NBA title. They did so, and Mayweather made $360,000. 

Haralabos Voulgaris Bets The House on The Lakers 

One of the most successful sports bettors of all time got his big start in basketball. Back in the year 2000, Los Angeles-based philosophy student – and former baggage handler at LAX Airport – Haralobos Voulgaris, built a basketball betting analysis system. That made him $30,000 in a year. He then put it all on the Lakers to win that year’s NBA title.

At the time, the bookmakers, and many experts, thought the LA team was washed. However that year the team’s stars clicked together, led by Shaquille O’Neil and Kobe Bryant and they kicked off a dominant few years with a playoffs win. Netting Voulgaris $500,000. 

He turned that money towards further NBA betting profits and then various businesses. He was later hired as a sports data analyst for the Dallas Mavericks. Now in his 50s, Voulgaris is a multimillionaire who owns a Spanish second division soccer team.

NBA Stars Gambling Exploits Post Career 

On top of those big NBA betting winners, several major basketball stars have been well known gamblers after their careers on the court wrapped up. Some big gambling basketball stars include:

• Michael Jordan
• Charles Barkley
• Allen Iversen
• Rex Chapman

Most of these stars have occasionally been spotted at Las Vegas casinos or posted about their gambling since leaving the game. There is no suggestion any of them bet on basketball while involved in the game professionally.

Jordan, probably the greatest basketball player of all time and certainly the richest, was a prodigious gambler at some points in his life. 

He reportedly used to wager hundreds of thousands on casual golf games with his friends and acquaintances, and apparently once put down $100,000 on a game of Rock, Paper, Scissors. 

Barkley famously placed a $500,000 on the Patriots in the 2002 Super Bowl, reportedly impressed by the talents of the-then rising star Tom Brady.

The Patriots won that game, despite being hefty underdogs, netting Barkley $2.2 million. And, as for Brady, he only went on to become one of the most successful NFL quarterbacks of all time.