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.
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.
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.
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.
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.
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.
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.
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.
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.
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:
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.
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.
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.