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The Biggest Gambling Losses of All Time – Top 10


lottery jackpotsRobert Maxwell £1.5m / $2.25m

Robert Maxwell was a famous media tycoon well known across the world, especially in the United Kingdom. He loved money, which is likely why he loved gambling. Maxwell gambled £1.5m in a little under three minutes playing multiple roulette wheels at the Les Ambassadeurs Casino in Mayfair, London.

Maxwell was convicted of fraud and died on November the 5th 1991 owing billions in pension fraud, so the money he was gambling wasn’t even his.

lottery jackpotsJimmy White £2.9m / $4.4m
World famous professional snooker player Jimmy White was known as the Whirlwind, not just for his skills on the table, but also his fast living. Jimmy made vast sums in the eighties and nineties from tournaments and sponsorship money, but most of his money went on drink, drugs, hookers and gambling.

He estimates his total losses around £2m on gambling, £200k on drugs untold amount of drink and booze. On one particular occasion lost £128,000 in one session in the bookies after coming runner-up in 1994, and that was long before FOBTs had made an appearance.

lottery jackpotsAkio Kashiwagi £7m / $10.5m
Mr Kashiwagi was a prolific baccarat player, who also enjoyed dabbling in high limit games of blackjack. Prior to his death in 1992; Mr Kashiwagi was stabbed 150 times in his native Japan, he played baccarat for between $100,000 and $200,000 a hand, with playing sessions lasting up to 80 hours.

Regarded as a Whale in both Las Vegas and Atlantic City, his untimely death left casinos been owed at least $9m.

lottery jackpotsFrank Sarakakis £10m / $15m
Frank Sarakakis was a Greek multi-millionaire in the car industry, and also a prolific roulette player. A regular at the Crockfords Casino in London, Mr Sarakakis lost £8m playing roulette in 1994, which follows on from a prior roulette blow-out at the Ritz in 1988 where it is estimated that he lost around £6m.

Although it is difficult to get an exact figure, his roulette losses are estimated to be around £10m.

lottery jackpotsGreek Tycoon £16m / $24m
Another Greek tycoon was reported to have lost in the region of £16,000,000 in visits to various London casinos, most notably the Ritz. It’s a shame he didn’t invest it in his own country, Greece could sure do with that money now.

top 10 gamblingArchie Karas £40m / $60m
Archie has an interesting story; in 1992 to 1995 he went on the longest winning streak in gambling history, turning $50 into an incredible $40m playing high stakes poker. But that clearly wasn’t enough, and although he wanted more, Archie went on to lose the entire amount in just three weeks playing craps and baccarat. His story however doesn’t end there, in 2013 Mr Karas was arrested for marking cards at a blackjack table, using a hollowed out chip to mark J, Q, K, A.

When police raided his house they found hollowed out chips from multiple US casinos, which surely brings in to question his poker playing skills!

top 10 gamblingOmar Siddiqui £42 / $65
Omar Siddiqui, from San Francisco, USA earned ‘only’ $225,000 a year as an executive at an electronics firm. I say only because his gambling produced losses in the millions, with a massive $8m lost in a single day.

Casinos wanted him in their establishment, and loaned him millions on the strength of his signature alone. However Mr Siddiquis’ house of cards was about to collapse, and was found to have committed fraud against his electronics company with underhand payments and hidden accounts. As well as never been able to pay off most of his casino debts, he also owed $21.5m to the IRS (tax).

top 10 gamblingTerry Watanabe £135m / $204m
Terry Watanabe is an American citizen who gambled the incredible sum of $205m is the space of a year, in two Harrah’s casinos on the Las Vegas Strip. Often playing multiple hands of high limit blackjack at $50,000 per hand, Mr Watanabe would regularly lose $5m a day!

He had lost $50m in 6 months, then doubled it to $100m just a month later. His year-end total according to Harrah’s records was $204m.

top 10 gamblingMaureen O’Connor £661m / $1b
There are not too many female gamblers who could be considered Whales, in fact Ms O’Connor is the only one on this list, however she’s made up for the lack of others by gambling to epic proportions with losses reaching $1b!

The widow to Jack In The Box founder Robert Peterson; Ms O’Connor was the former mayor of San Diego who went on to commit fraud against her former husband’s charitable foundation, as well as selling her multiple properties, jewellery and other high value items to fund her gambling addiction. Whilst in court in 2013 charged with multiple counts of fraud, Ms O’Connor’s losses were laid bare, and reached a little over $1 Bilion.

top 10 gamblingHarry Kakavas £990m / $1.5b
In a little over a year, Australian Harry Kakavas gambled away a little over $1.5b, mostly playing high limit blackjack, and the high rollers favourite; baccarat.
Almost the entire amount was spent in the Crown Casino on Australia’s Gold Coast, which was subsequently taken to court by Mr Kakavas. Mr Kakavas claimed that the Crown Casino were responsible for his losses and did nothing to prevent him from his excessive gambling even though it was obvious he had a serious problem.

He lost the case in 2013, and was deemed entirely responsible for his own actions.

TOTAL AMOUNT GAMBLED = £1.9B / $2.88B 


The sums here are depressingly large, and a lot of the list is made up from actions of fraud, so not only are they gambling, they are gambling other people’s money.

Gambling is fun, gambling addiction is not. If you think you have a problem, visit GamCare for a different perspective.

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