Determining the "richest" sports bettors is challenging because they often operate with secrecy, and public figures often generate wealth through multiple endeavors. However, several individuals are widely recognized as having accumulated massive fortunes primarily or partially through sports betting.

Some of the Richest / Most Successful Sports (and Gambling) Bettors

1. Bill Benter

   • Often considered one of the most successful gamblers ever. Wikipedia+2NewsWire Nigeria+2

   • He used mathematical models to bet on horse racing, especially in Hong Kong. Wikipedia+1

   • His estimated net worth from gambling is very high — sources put it in the hundreds of millions and possibly over $1 billion. The USA Leaders+2GambLizard+2

2. Tony Bloom

   • A professional bettor, poker player, and entrepreneur. The Frisky+2PlayToday.co+2

   • He founded Starlizard, a betting analytics firm. PlayToday.co

   • His net worth is estimated to be £1.3 billion (or more), making him one of the richest “bettors.” PlayToday.co+1

3. Billy Walters

   • Very famous American sports bettor. Wikipedia

   • Known for a decades-long sports betting career with very consistent winning. Wikipedia

   • His net worth is estimated to be around $200 million. Wikipedia

4. Edward Thorp

   • Mathematician, card-counter, and gambler. The USA Leaders+1

   • He made money from blackjack and then applied his statistical models to finance (hedge funds). The USA Leaders

   • His estimated wealth is very high; some sources put it around $800 million. The USA Leaders

5. Zeljko Ranogajec

   • Very secretive bettor; believed to run a large syndicated betting operation. BetZillion

   • His net worth is estimated to be in the hundreds of millions. PlayToday.co

✅ Who Might Be the Richest?

• Bill Benter is probably the strongest candidate for “richest pure pro gambler” (especially in terms of betting-based wealth), given his reported $1B+ value tied to his betting models.

• Tony Bloom, while extremely wealthy, has business interests beyond just betting (poker, owning a football club), so some of his wealth comes from other ventures — but he’s definitely among the richest bettors.

Real crazy facts:

• Wayne Shelton -- the bettor who placed a $100 parlay in May 2023 on Texas Rangers, Kansas City Chiefs and Oklahoma City Thunder championship futures into a $1.7 million wager -- has officially cashed out

• Drake has lost a total of over $8. Million after placing over $124. Million worth of bets. Throughout the 4-week. Period drake writes on the image "Got to share the other side of gambling.

• On Thursday afternoon, Circa Sports reported taking a $3.1 million wager on the Eagles moneyline (ML) against the Carolina Panthers.

• After selling his company, Watanabe became known for his lavish gambling habits. In 2007, he was reported to have lost $127 million at Caesars Palace and The Rio in Las Vegas after having gambled a total of $825 million. He was banned from Wynn Las Vegas for compulsive gambling.

• Michael Jordan owed over $1.2 million to businessman Richard Esquinas from golf bets alone. Juanita Jordan, his then-wife, admitted to writing $50,000 checks to cover his gambling losses. Jordan once reportedly lost $5 million in one night at a casino. These were not isolated incidents.

• In 2016, a Las Vegas bettor won $305K off a $5 parlay with a William Hill sportsbook. The bettor hit a ridiculous 15-leg parlay by picking straight up basketball winners on a progressive parlay card that had been offered by William Hill. Of the 15 games, the bettor selected 12 college hoop contests and two NBA games.

• Mattress Mack uh the famous furniture retailer down there in the Houston. Area is backing the Cowboys to the tune of $2. Million that's the bet he has put down on Super Bowl.

• Jake Paul's suicide bet: He bets his 40 million dollar purse that he beats Tyson. The Problem Child stakes all his winnings that he can stop Iron Mike Tyson. Boxing.

• Archie Karas - History's Greatest Gambler, who turned $50 into 40 million. Some called him a legend, others called him a gambler without limits. Archie Karas and his "The Run", when he turned $50 into a whopping 40 million, is still one of the wildest stories from the world of gambling even today.

• Here are the biggest reported bets that cashed in legal U.S. sports betting history:

  • $8 million on Oklahoma City Thunder (-700) to win 2024-25 NBA championship.

  • $3.46 million on Tampa Bay Buccaneers +3.5 (-127) in Super Bowl LV.

  • $3.1 million on Philadelphia Eagles ML (-700) to beat Carolina Panthers in Week 14.

• Has a 25-leg parlay ever hit?

  A Fanatics Sportsbook customer did that over the weekend on a 25-leg parlay. Yes — 25 legs. And that person's bank account is five figures larger today because of it.

• After Mike Tyson fight with Jake Paul, which earned him $20 million, he gave the entire amount to his wife—the woman who stood by him during his darkest days. Tyson was a legend, but he experienced bleak times when he went bankrupt, lost his way, and was abandoned by previous relationships.

• What is Jake Paul's net worth? Logan Paul's brother Jake has an estimated net worth of $100 million, as reported by Celebrity Net Worth. He ranked behind Logan at No. 13 on Forbes' Top Creators (2024).

• Does Donald Trump still own the Taj Mahal casino?

  In February 2016, Trump Entertainment Resorts exited bankruptcy and became a subsidiary of Icahn Enterprises. The casino retained the name "Trump Taj Mahal", though Donald Trump no longer held any ownership stake.