Top gambling losses

No one likes to take a gambling loss. Most gamblers will take the attitude of “Win some, lose some”. For obvious reasons people don’t like to broadcast losses. Occasionally the amounts involved can be so big that they make the wrong type of racing history. This article examines a few top losses and the story behind them. There are, without a doubt, bigger losses, but we will never get to hear about them. As ever, when the fun stops, stop. For entertainment purposes, let’s count them down:

Terrance Watanabe – Lost his entire fortune

Mr Watanabe inherited a huge slice of the “Oriental Trading Company” when his father, the company founder, died. This company was essentially the forerunner of Amazon and provided value products made in low-cost countries in the US. In 2000 he resigned as CEO and sold all of his stake. He went on to become a high-rolling degenerate gambler. It is rumoured that during the period of his gambling, he lost in excess of $127,000,000 at the tables (Rather than horse racing or sports betting).

He is still around, but apparently no longer a high roller. An interesting side story is that the casino involved was fined and reprimanded for allowing Watanabe to gamble whilst intoxicated. This comes alongside the stories of his over-friendly manner with female staff at the casino. This didn’t deter them from creating significant perks for Watanabe, including half a million in shop credit, paying for his airline flights and even creating a new tier of gambling whale for him.

Moral of the story… Gambling, whilst sad or drunk, rarely works out well.

Charles Barkley

Barkley was an NBA player for the Phoenix Suns, so he had some degree of wealth. He was also known as a bit of a wild card on the court, having multiple “discussions” with team mates and opposition alike. Barkley himself admitted to losing $2.5 million in one six-hour period. He also had major wins, but essentially a whopping total gambling loss where he gambled away his $30 Million fortune over the course of several years. He even ended up being sued by a Casino that claimed he had failed to pay a $400,000 outstanding balance. It was settled in a timely fashion, but given his earning power was starting to wain, it hit home that he had to stop gambling. Fortunately, he was able to carve out a new career in TV.

Umar Siddiqui

A relative unknown, but this one turned criminal. Most people of a certain age are aware of Fry’s Electronics, a now-closed big electronics retailer. During the late 90s, it was the go-to store for technology before the Internet became what we know it as today.

He was a quick blackjack player and had a penchant for the more expensive things in life. Despite his quarter-of-a-mill salary (in 2005 values), he cooked the books enough to be able to transfer $70,000,000 into his account at his preferred Casino during a three-year period. The FBI put his total spending at over $160,000,000. Obviously, spending at that level gets a whole new level of perks and his reputation as a whale proceeded him wherever he went. It all came crashing down for him later, though, as he was jailed for six years for wire fraud and money laundering. He went on to declare bankruptcy in the end.

Moral of this story… Don’t do stupid stuff with stolen money.

Patrick Foster

Bringing the whole “Oops, I lost a lot of dosh” in gambling losses to levels most people can understand and rounding out our little foray into gambling losses, a chap called Patrick Foster. Not a big loser but a warning to readers. His loss, compared to the people listed here, is quite small but much more relatable. He managed to end up with £250,000 of gambling debt. He admits to placing massive bets, including fifty thousand on a single horse race. Read his story of gambling highs and lows.

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