Gamblers Who Lost It All – The Biggest Losses in History

There is always a risk when you sit down at a casino table, but big losses aren’t too common if you are smart enough. Well, for the gamblers who lost it all the temptation has proven too difficult to resist. Whether they were taking an ego trip or looking to recoup investment is beyond the point.

What matters is that the following famous gamblers who lost it all make a good anecdote, but are a rather poor example of how to behave and act in a casino. They have lost it all, and more. Today we present to you the gamblers who went from riches to rags, or at least lost a substantial chunk of their fortune gambling.

1. Terrance Watanabe

• Total amount gambled: $825 million
• Incurred losses: $127 million
• Does he owe anything today? $15 million (August 2020)
• Game of choice: Baccarat, Blackjack

When we discuss the biggest gambling losers in history there is always a bit of a rivalry. As it turns out, a lot of people who came into money, or made a fortune one way or another, have felt inclined to gamble rather foolhardily at one time or another. But if anything, Terrance Watanabe is truly one of the gamblers who lost it all, or at least a very substantial part of what he owned.

Watanabe inherited Oriental Trading Company in 1977 which he later sold in 2000. Whether he was bored or wanted to try something new, Watanabe’s gambling habits pushed him into more extreme scenarios year after year and in 2007 he incurred $127 million in losses at Caesar’s Palace and The Rio after gambling over $825 million.

So far as famous gamblers who lost it all go, Watanabe’s losing streak is believed to be the biggest Las Vegas has ever seen. He tried suing the casinos, but ultimately lost and was ordered to pay off his debt.

Today, Watanabe has covered almost his entire debt except for $15 million for which he faced four felony charges back in 2009 and again in 2020. He could be sentenced to 28 years in prison if he fails to pay up.

2. Harry Kakavas

• Total amount gambled: $1.43 billion
• Incurred losses: $20.5 million
• Does he owe anything today? He has paid his debt in full.
• Game of choice: Baccarat

Harry Kakavas may not be the biggest loser, but he has made a point of being a repetitive loser. Yet, if anything, Kakavas has had the prescience, skill, and knowledge to minimize his losses in a way that has allowed him to certainly not incur the biggest losses out there.

Over the course of 16 months, Kakavas played baccarat at the Melbourne Crown Casino and spent a total of A$1.43 billion between 2012 and 2013, incurring net losses worth A$20.5 While Kakavas has had no trouble spending 16 months gambling, he has certainly objected to the casino keeping the A$20.5 million he lost.  

In a lawsuit filed with the High Court of Australia, Kakavas claimed that the casino had exploited his “pathological urge to gamble,” a popular defense between famous gamblers who lost it all, or at least enough to feel irritated.

The presiding judge explained that Kakavas had shown “rational decision making and was able to act in his own best interest”, including the plaintiff’s decision to refrain from gambling from time to time, the judge’s ruling stated.

3. Maureen O’Connor

• Total amount gambled: $1 billion
• Incurred losses: $13 million
• Does she owe anything today? She has paid her debt in full
• Game of choice: Video poker

She served as a mayor of San Diego and her gambling habits quickly spiraled out of control. You could argue that where there is power, there is money, but in the case of Maureen O’Connor, her obsession with gambling quickly took a turn for the worst.

Yet, compared with other unfortunate gamblers, O’Connor has done quite well in mitigating risk, perhaps something that politicians are hardwired to do. She gambled over $1 billion, but her losses ran to “only $13 million.” Better than Kakavas’ and certainly much better than Watanabe’s own record.

O’Connor is certainly one of the gamblers who lost it all, having had to borrow $2 million from her second husband’s charitable foundation and spent the money on video poker. O’Connor is also the widow of Robert Peterson, founder of Jack-in-the-Box restaurant.

While her gambling addiction is certainly a little sensationalist for good taste, O’Connor is worthy of admiration. Her political and professional career was based on merit and everything she achieved came at the expense of hard work.

4. Archie Karas

• Total amount gambled: $40 million
• Incurred losses: $40 million
• Does he owe anything today? No
• Game of choice: Poker, Baccarat, Dice

Archie Karas is one of the most iconic gamblers who lost it all. Known for his appetite to play big, Archie had no trouble taking on any risk for a chance at something better. He arrived in Las Vegas in December 1992 with just $50 to his name and a $10,000 loan that would come a bit later. Over the course of the next two years, Archie was playing poker intensely, amassing the fantastic $40 million in the process.

But the way it began was with a destitute Archie spotting a familiar face at The Mirage and requesting the $10,000 loan that would set the wheels of fortune in motion. He quickly turned the money into $30,000 playing $200/$400 limit Razz and paid back $20,000 to his beneficiary.

Thus began Archie’s tour around Las Vegas amassing fortunes in casinos all over the place and winning $3 million at Binion’s Horseshoe. His bankroll gradually grew up to $5 million, and then $7 million, but Archie was done looking for opponents.

Instead, he would just lay out the money on a table and wait for an opponent to approach him. Many were interested, and not least Stu Ungar, one of the most popular if somewhat tragic players. Archie beat Stu in two consecutive games.

The first one was heads-up Razz, which cost Stu $500,000, and then he secured a victory in 7-Card Stud, claiming an additional $700,000. Karas played and won against many of the time’s best players, including Chip Reese, Puggy Pearson, and Johnny Moss, but his downfall began when he turned away from skilled-based games and trundled into the world of uncertainty playing dice and baccarat. Why take on the risk with more chancy games? Well, who better to explain that than the man himself.

“You’ve got to understand something. Money means nothing to me. I don’t value it. I’ve had all the material things I could ever want. Everything. The things I want, money can’t buy: health, freedom, love, happiness. I don’t care about money, so I have no fear. I don’t care if I lose it.”

Archie Karas

Archie would bargain with the casino to allow him to bet way above the limit. At one point he even won all of Binion’s $5,000 denomination chips, leaving the casino short of its highest chips at the time.

He managed to lose his $40 million in a period of three weeks, quickly going from one of the most successful gamblers to one of the most tragically unfortunate. Truly, Archie is one of the most famous gamblers who lost it all.

5. Charles Barkley

• Total amount gambled: $30 million
• Incurred losses: $30 million
• Does he owe anything today? No
• Game of choice: Baccarat, Roulette, Dice, Blackjack

The Phoenix Suns ace has had a handful of unfortunate brushes with gambling addiction, and that is no secret. Charles Barkley lost an estimated $30 million to gambling, which was his entire fortune. Yet, his gambling proclivities have never been a source of regret to Barkley who has always been open about his addiction.

During his stint as an active gambler, he must have lost millions worth of dollars playing at 30 different casinos, he argued. It’s interesting to see his opinion on the matter. Where others have vituperated and tried suing casinos, Barkley has been more reflective on his habits, accepting the good and the bad:

“I went to Vegas a bunch of times and won a million dollars. Probably 10 times. But I’ve also went to Vegas and lost a million probably three times as much.”

Charles Barkley

If Barkley is one of the gamblers who lost it all, he certainly doesn’t have the look. While he has burned through most of his fortune, he was never worried about getting addicted. His gravest mistake, he admitted, was to travel to Las Vegas and expect to win one million on each trip. Rather, though, he ended up losing a lot.

Over time, Barkley developed a philosophy where he took each loss in stride and felt comfortable with incurring losses up to $200,000 on a session. “I love the action, I love the justice,” he explained, but added that was important to do everything in moderation he concluded.

Charles Barkley is an interesting person. He is definitely one of the most famous gamblers, and he lost it all – or most of it. Yet, he has kept cool about it.

6. Michael Vick

• Total amount gambled: $20 million
• Incurred losses: $20 million
• Does he owe anything today? No
• Game of choice: Running an illegal betting ring

Michael Vick’s past is mixed but mostly of his own making. Vick is definitely one of the gamblers who lost it all, but not in just a purely financial sense. The former National Football League (NFL) player and one of the best quarterbacks the Philadelphia Eagles have ever hired had an issue with gambling.

Vick was running an illegal interstate dogfighting ring, known as the Bad Newz Kennels, and he himself provided most of the money for the gambling side of the operation. He was immediately suspended by NFL Commissioner Roger Goodell who argued that Vick’s conduct breached not only professional guidelines established by the league, but was also highly unethical due to the nature of the activity. The Atlanta Falcons, the team Vick was playing for at the time, didn’t sit idly by as well.

They sent a letter to Vick saying that he now had to reimburse them for $20 million of the $37 million he received as a bonus. The court sided with the Falcons, ruling that Vick had used the bonus money to fuel the gambling ring.  

After a long and sinuous proceeding, he was sentenced to 23 months. The sentence against him cited a failed drug test and a failed polygraph, which, in the jury’s opinion meant that Vick had failed to take full responsibility for his actions.

Despite his past mistakes, Michael has paid for his sins and he’s back in the public eye. He joined FOX as an NFL studio analyst, a position which he deserves. So far as famous gamblers who lost it all go, though, Michael Vick is definitely one.

7. Frank Saracakis

• Total amount gambled: $13 million
• Incurred losses: $13 million
• Does he owe anything today? No
• Game of choice: Roulette

Frank Saracakis was the heir of the Greek Automobile Company who took a trip to London in 1995 and decided to indulge in his pastime of gambling. Tempted by the glitz of the Melting Pot, he quickly bought chips worth $13 million at the London’s Crockford’s Casino.

His game of choice was roulette which he spent playing for several hours before we lost every single chip he had in his possession. Certainly, Saracakis isn’t one of those gamblers who lost it all, but he certainly incurred one of the biggest losses and is a worthy addition to our list.