This article brings together publicly reported cases of major losses in casinos, betting, and other forms of gambling. The figures are estimates and are based on publicly available sources, which span different years and gambling formats. All amounts are given in U.S. dollars, though the original reports may have used other currencies.
Quick navigation: from the largest losses to the smallest:
- Maureen O’Connor — about $1 billion
- Harry Kakavas — over $160 million in a single day (total wagers up to $1.5 billion)
- Terrance Watanabe — about $205 million
- Omar Sadiki — up to $160 million over a decade
- Archie Karas — about $40 million
- Kerry Packer — about $42 million in a year
- Charles Barkley — about $20 million over his career
- Akio Kashiwagi — million-dollar swings at baccarat
- Jimmy White — more than $3 million
- Robert Maxwell — more than $2 million in three minutes
The record for single-day losses belongs to Harry Kakavas. By most estimates, the Australian developer lost over $160 million in under six hours. This episode clearly shows how quickly money disappears when a high roller has access to VIP table limits, unlimited credit, and generous comps and incentives from the casino.
The former mayor who lost a billion on video poker
Maureen O’Connor, the first woman to serve as mayor of San Diego, left a fortune at video poker machines throughout the 2000s. Her total losses are estimated at about $1 billion, and her accumulated debt totaled around $13 million. To keep gambling, O’Connor, according to investigators, misappropriated $2 million from her late husband’s charitable foundation.
She avoided a prison sentence. The conditions included repaying the foundation and seeking professional help for her addiction.
Six Hours for Kakavas—and a Courtroom Loss
Over 14 months, Harry Kakavas wagered about $1.5 billion on baccarat at Melbourne’s Crown Casino. The peak came when more than $160 million was lost in under six hours. The developer accused the casino of deliberately encouraging him to keep gambling through lavish perks. However, in 2013 the High Court of Australia dismissed the claim, finding that the player fully understood his actions.
$205 million in a year and 6% of Harrah’s gaming revenue
Terrance Watanabe, heir to Oriental Trading Company, left about $205 million in Las Vegas over a year, betting up to $50,000 per hand. These losses amounted to roughly 6% of Harrah’s Entertainment Inc.’s annual gaming revenue. Watanabe later claimed the casino enabled his addiction by supplying alcohol and painkillers. The ensuing legal battle highlighted ethical questions about how casinos treat their biggest clients.
From executive to inmate
Omar Sadiki, a senior executive at an electronics company, lost $65 million in Las Vegas casinos over three years. Total losses over a decade are estimated at $160 million. To keep gambling, Sadiki began siphoning money from his employer, for which he was sentenced to six years in prison on fraud charges.
Archie Karas’s “The Run”—and How It Ended
Archie Karas became famous for turning $50 into $40 million between 1992 and 1995, playing craps and baccarat. He then lost it all the same way. In 2013, Karas was arrested on charges of marking cards at a blackjack table, which cast doubt on the legitimacy of his legendary winning streak.
Kerry Packer and $20 million in three days
The Australian media mogul and billionaire lost about $42 million from September 1999 to August 2000. Of that, $20 million was lost during a three-day baccarat session in Las Vegas. His action was large enough to materially affect the casino’s quarterly results. Packer, however, was also known for generosity: according to one story, in a single evening he paid off a waitress’s mortgage.
The NBA star who admitted to $20 million in losses
Charles Barkley, named one of the NBA’s 50 Greatest Players, publicly estimated his total losses at about $20 million. One of the most painful episodes, he said, was a $500,000 bet he later called one of his biggest regrets.
Akio Kashiwagi’s baccarat—and an unsolved murder
Japanese developer Akio Kashiwagi bet as much as $200,000 per hand at baccarat, experiencing million-dollar wins and losses. At the Trump Plaza Hotel and Casino, he won about $9 million in a single session. In 1992, Kashiwagi was killed in his home near Mount Fuji. Media reports linked his death to large debts and possible contacts with the yakuza, but the case was never solved.
The snooker player who lost more than titles
Jimmy White, a six-time World Snooker Championship finalist, lost more than $3 million on horse racing, blackjack, and other bets. Gambling problems were accompanied by struggles with alcohol and drug addiction. White later publicly spoke about what he went through and his recovery.
Robert Maxwell’s Three Minutes
Media mogul Robert Maxwell lost more than $2 million in under three minutes at London’s Les Ambassadeurs casino. This episode became emblematic of his appetite for risk. After Maxwell’s mysterious death at sea, it emerged that he had siphoned money from his companies’ pension funds.
What all ten stories have in common
Access to high limits, unlimited credit, and VIP incentives can turn a big bet into an avalanche. Against the backdrop of addiction, losses accelerate, and the consequences go far beyond money, affecting careers, freedom, and life.
This is more relevant than ever today, as online casinos make it possible to place bets 24/7, so there’s virtually no loss limit. In addition, more and more gaming platforms offer free spins no deposit required, which significantly lowers the barrier to entry. Players become less afraid of losing money – and this effect does not go away even after they start playing for real money with their own deposited funds.
In online casinos, there’s no transparent system for tracking record wins and losses. However, many famous people openly admit how much they have lost. For example, rapper Drake spoke about losses of more than $8 million over a short period. Lil Baby mentioned similar amounts. He also noted that after such a major loss, he temporarily stopped gambling.
Where to get help if gambling has gotten out of control
For those who have faced problem gambling addiction, confidential support services are available. One such organization, GamCare, offers counselling, support, and recovery programs. Seeking help early can prevent losses measured in more than money.
This was a fascinating and eye-opening read. The stories clearly show that gambling addiction can affect anyone, regardless of their wealth, fame, or success. I appreciate that the article doesn’t just focus on the huge financial losses but also highlights the personal, legal, and emotional consequences that often follow. Ending with information about seeking professional help was especially important, as it reminds readers that responsible gambling and early support can make a real difference.