Gambling has always been a high-stakes game, but some players have taken it to another level by placing bets worth millions. These wagers have either resulted in record-breaking winnings or devastating losses, proving that fortune can change in an instant. Below, we explore ten of the most expensive bets ever placed in gambling history.
The Legendary Baccarat Bets of Phil Ivey
Phil Ivey, one of the most successful poker players in history, made headlines not for poker, but for baccarat. In 2012, he placed a series of bets amounting to £7.7 million at Crockfords Casino in London. Using a controversial strategy known as ‘edge sorting,’ he managed to win a fortune. However, the casino refused to pay out his winnings, claiming he had gained an unfair advantage.
The legal battle that followed lasted for years. Courts ultimately ruled against Ivey, deeming his strategy unethical. Despite this, his bets remain among the largest ever placed in baccarat, demonstrating how professional gamblers use every edge to their advantage.
This case set a legal precedent, warning casinos worldwide about the risks of high-stakes gamblers employing advanced techniques to tilt the odds in their favour.
Why the Ivey Case Changed Gambling Regulations
The Phil Ivey baccarat controversy led to tighter regulations in casinos worldwide. Many establishments revised their card-handling policies and introduced more rigorous security measures to prevent similar incidents. Additionally, the ruling reinforced that casinos have the final say in large disputed winnings.
For gamblers, the case highlighted the importance of understanding casino rules before placing massive bets. Even if a strategy is technically legal, it may still result in the casino withholding winnings if deemed unfair.
Ultimately, this high-stakes bet serves as a cautionary tale for professional players and casino operators alike.
Archie Karas and the Greatest Winning Streak
Archie Karas is famous for turning $50 into over $40 million during a legendary gambling streak in the early 1990s. His most expensive bets took place in Las Vegas, where he wagered millions at high-stakes poker, craps, and baccarat tables.
Karas’ incredible run saw him defeat some of the world’s best poker players, including legends like Stu Ungar and Doyle Brunson. At his peak, he was playing with chips worth millions in his pocket, betting sums that no casino had seen before.
However, his luck ran out. Over a few weeks, he lost everything he had won, proving that no streak lasts forever in the world of gambling.
The Psychology of High-Stakes Gambling
Archie Karas’ rise and fall is a textbook example of gambling psychology. The thrill of winning can make even the most disciplined players take greater risks, often leading to massive losses.
Casinos closely monitor high-rollers, offering them luxury treatment to keep them playing. While some walk away with fortunes, many lose more than they ever expected.
Understanding when to stop is a crucial skill in gambling. Even the greatest winning streaks can end abruptly, making it essential for players to manage their bankroll wisely.

The $5 Million Bet by an Anonymous Whale
One of the biggest single bets in history was placed by an anonymous high-roller, known as a ‘whale,’ at a Las Vegas casino. In 2017, this mysterious gambler reportedly wagered $5 million on a single hand of baccarat at The Venetian.
The details of the outcome remain undisclosed, but sources suggest the player walked away with a massive win. Such bets are rare, as even casinos hesitate to accept wagers of this magnitude.
This event highlights the immense risks and rewards of high-stakes gambling. While some casinos welcome such bets, they also impose strict financial limits to protect themselves from potential losses.
How Casinos Handle Massive Wagers
Casinos have dedicated teams to manage high-roller bets. These include risk analysts who determine the financial impact of large wagers and set betting limits accordingly.
Most establishments also require advance notice for multi-million-dollar bets, ensuring they can cover potential payouts. In some cases, casinos negotiate with the player to set customized betting limits.
Despite these precautions, massive bets like the $5 million baccarat wager demonstrate the allure of high-stakes gambling and the financial strategies behind casino management.