Archie Karas ($40 Million)
Archie ‘The Greek’ Karas will go down in history as one of the most famous gamblers and poker players ever. He holds the title for the longest documented winning streak in gambling history. From 1992 to 1995 and starting with only $50 to his name, he managed to turn that paltry sum into a fortune of 40 million. But this wasn’t enough and rather then quit while he was ahead, he wanted more.
The Greek lost nearly his entire $40 million bankroll within a couple of months. The losing streak started with a 3-week period in which Archie lost $30 million at the Binions Horseshoe casino. First, he lost $11 million at the dice table. Frustrated and disappointed of his mistake that he did not stop after the first $3-4 million, Archie returned to the casino on the next day, this time to play high-stakes baccarat. Again, he convinced the casino management to raise the limits just for him to $300,000 per bet. Within ten days, the Greek lost 17,000,000 in baccarat.
Between those games Archie tried to play some poker and win back some of the money he lost against the casino, but instead he lost another $2 million to Chip Reese in $10,000/$20,000 heads up poker games. In a three-week period, Archie lost $30 million. After that disaster he decided to take a couple of weeks off on vacation and go home to Greece.
As soon as Karas returned to Las Vegas from his vacation in his native country, he went to the casino. Deja vu right? In less than a month he lost the rest of the staggering $40 million he won in the last nearly three years.
In September 2013, he was arrested in Las Vegas after being accused of marking cards and using hollowed-out chips to mark J, Q, K, and A at a blackjack table at a San Diego casino and he faced three years in prison for it.
Kerry Packer ($42.6 Million)
Kerry Packer built a media empire during his lifetime and became known as Australia’s richest man and wildest gambler. He would routinely bet $450,000 on a blackjack hand and leave waitresses a seven-figure tip when visiting casinos. It is said that he once wagered nearly $25 million spread on four roulette table and lost it all.
Due to his high-stakes gambling ventures in blackjack poker and baccarat, he managed to lose 42 million in less than a year (Between September 1999 to August 2000). He also reportedly lost more than 20 million during a three-day baccarat tournament during the weekend in Las Vegas.
Packer is quoted for an exchange in a poker tournament at the Stratosphere Casino, where a Texan oil investor was attempting to engage him in a game of poker. Upon the Texan saying “I’m worth $60,000,000!” Packer apparently pulled out a coin and asked nonchalantly, “heads or tails?”, referring to an A$120 million wager (according to Bob Stupak’s biography). Some variations of the story put the sum at $60 million to $100 million and claim the line was “I’ll toss you for it”.
Zhenli Ye Gon ($125 Million)
Zhenli Ye Gon moved from Shanghai to Mexico in 1996 to work in the import/export business. By 2002, he was running a supposedly legitimate chemical importing company called Unimed Pharm Chem. Somewhere along the way, Mr. Ye Gon allegedly began re-directing a portion of his imports from legitimate businesses to the Sinola drug cartel. The cartel then used these precursor chemicals to manufacture massive quantities of crystal meth which were then shipped to the US.
Between 2004 and 2007, Ye Gon had reportedly blown away $85 million at the Venetian in Las Vegas and $40 million at several other major casinos. His losses were so large that it even affected the bonuses of Las Vegas Sands and Venetian executives. Mexican drug agents and the American DEA officials raided his mansion in Mexico City in 2007 and seized $210 million cash hidden in floors.
Zhenli Ye Gon was indicted in The United States in 2007, but after a series of witnesses recanted or coincidentally turned up dead, the case was eventually dismissed.
Omar Siddiqui ($162 Million)
Omar Siddiqui is a Pakistani-American and former vice president of Fry’s Electronics.
Siddiqui reportedly wire transferred $70.4 million to The Venetian between 2005 and 2008. He was known by casino employees as a “blackjack machine”, according to one casino industry veteran “you couldn’t deal fast enough”. Siddiqui gambled so fast he would “red line the house limit”. Siddiqui was also known as a lavish spender who enjoyed fast cars, bottles of Dom Perignon Rose and bowls of Glitterati Mentissimo peppermints.
He is known to have gambled over $162 million in Las Vegas from 2005 to 2008 after embezzling money from his employer through money-laundering and wire fraud.
Suspicion began in 2005, when an employee saw “confidential spreadsheets, letters and extraordinarily high commission amounts on Siddiqui’s desk”. Siddiqui had claimed he was a co-owner of the company. One company, Phoebe Micro of Fremont, claimed it was the victim of Siddiqui. General manager, Peter Liu said Siddiqui asked to pay a “high marketing fee so Fry’s would prominently display Phoebe’s products”.
He pled guilty and declared bankruptcy in 2011 after remaining listed as $137 million in debt.
Terry Watanabe ($204 Million)
The American-born businessman, whose father founded the plastic trinket business “Oriental Trading Company”, reportedly gambled and wasted away $205 million in just one year. His gambling spree took place at two Harrah’s casinos on the Las Vegas Strip; the Caesar’s Palace and the Rio. He often played multiple high-priced hands of blackjack at $50,000 per hand. But he would lose regularly, even losing 5 million in just one day. 50 million in six months and $100million a month later. Harrah’s Entertainment Inc reported the 6% of its gambling revenue that year, came solely from Watanabe.
Caesars Entertainment Corporation was fined $225,000 by the New Jersey Gaming Commission for allowing Watanabe to continue gambling in a highly intoxicated state, though Watanabe’s losses occurred in Las Vegas. Caesars alleges that Watanabe "was using marijuana and/or cocaine and made sexual advances toward employees". Caesars Rewards created a special tier for him known as "Chairman" which ranks above "Seven Stars". Watanabe received "tickets to the Rolling Stones, $12,500 a month for airfare and $500,000 in credit at the gift stores. Harrah’s also offered 15% cash back on table losses greater than $500,000, special high-limit games and other incentives".