Top 5 Richest Gamblers and Their Biggest Winning Bets
By
Jane Shaw
Senior Editor Updated: 04/09/2025
We count on Jane to inform our readers about the latest slot games in the US market. With her passion for video games and a degree in engineering, she’s our gambling tech expert. Jane’s also active in our blog section, where she tackles the curiosities and changes in the industry.
The richest gamblers always plan their bets
Hitting the jackpot is every gambler’s biggest dream and that includes some of the richest gamblers in the world. Whether it’s due to a lucky lottery ticket or careful analysis of a horse race, there are many success stories. Check out this article to learn about some of the richest professional gamblers and their big wins.
1. David Walsh – $60 million
While David Walsh is well-known for being the founder of the MONA art gallery in Tasmania, he is also among the world’s top gamblers. He is close friends with Zeljko Ranogajec and even built the software used by Ranogajec’s syndicate to predict horse races. Early on, they solidified their friendship by frequenting Vegas together to play blackjack.
If you’ve had a system that works for 20 years, it’s not as a result of skill. You acquire the system that worked by luck, then once it worked, it might keep working.
Walsh attributes his wins to luck but has had two major wins over the years. In 2022, he worked with Ranogajec’s syndicate to buy $11 million worth of lottery tickets, which turned into a $60 million jackpot prize. The syndicate would also win a $63 million prize from a horse race in Tokyo on Christmas Eve 2021.
2. Kerry Packer – $20 million
Born in Sydney, Australia, Kerry Packer was one of the richest professional gamblers in the world. He was a media tycoon, owning the Nine Network, and founded World Series Cricket. Packer was known for being a high roller, often winning big to the point casinos had to set hard bet limits for him. Here are some of his notable wins:
- $6 million on a bet at the 1997 Melbourne Cup
- $10 million on another bet at the 1998 Melbourne Cup
His biggest win would come in May 1995 when he visited the MGM Grand. After just 40 minutes of playing blackjack with bets of $250,000, he won $20 million. This win cemented him as the richest blackjack player and became an inspiration to many players at the best blackjack sites.
3. Bill Benter – $16 million
Bill Benter is renowned for being one of the richest gamblers and for his impressive algorithm. Like the other gamblers on this list, he began playing blackjack and poker before eventually moving to horse racing with Alan Woods. While the two would separate due to a dispute, Benter would work on improving his horse racing algorithm.
A substantial portion of our success is attributable to the pioneering work done by Benter.
Until Benter, people thought horse racing was too random as there were many factors to consider. However, using his computer algorithm, Benter took the official odds and factored in the horse’s size, jockey skill, straight-line speed, etc. He would win Hong Kong’s Triple Trio bet in 2001, predicting the first three horses in three races, earning $16 million. However, the prize was unclaimed and donated to charities.
4. Zeljko Ranogajec – $7.5 million
Although he’s friends with Walsh, Ranogajec is famous in his own right for his skill in gambling. While not the richest poker player, he and Walsh used to play various card games at Australian and Vegas casinos. Soon, they would establish the Bankroll syndicate, which bets around $3 billion on yearly horse races.
We’re called Bankroll Punters Club, that’s what we call ourselves. Customers that bet on our level number in the handful in the world.
Ranogajec likes to keep his dealings secret, so knowing how much he wins isn’t easy. His biggest recorded win came in 1994 when he won a $7.5 million jackpot on keno. While Ranogajec often plays with stakes higher than those at high stakes roulette in the US, he has found a lot of success with the syndicate.
5. Tony Bloom – $1.5 million
Tony Bloom can be considered among the richest poker players, with his total winnings exceeding $3,800,000. Having studied mathematics at the University of Manchester and with a passion for poker, he has appeared in many tournaments. Here are a few of the most notable events he has played in:
- Australasian Poker Championship
- World Series of Poker
- World Poker Tour
- European Poker Tour
- PokerGO Tour
Despite this, his biggest win comes from horse racing. He’s an entrepreneur who owns the horse Energumene, which competed in the 2023 Champion Chase during the Cheltenham Festival. After placing a bet of £400,000, he would win a total of £1.2 million (£560,000 from the win and £220,000 for being the owner).
Conclusion
While these are just a few success stories, even the richest professional gamblers have experienced losses. For example, Benter and Woods lost $120,000 during their first time in Hong Kong. That’s why you should always gamble responsibly by following a few rules:
- Prepare a budget
- Take frequent breaks
- Set personal loss limits
- Check the game’s bet limits
All legitimate sites also have responsible gambling tools and allow you to contact responsible gambling organizations. Even with the best systems, luck still plays an important part, so you should always plan your bets carefully.
