Poker’s Greatest All-Time Whales: Riddle, Chagra and Karas

The "whale" is the holy grail of poker - a big-moneyed, amateur poker player with a bottomless bankroll, an eye for the gamble and next-to-no sense of what's truly happening on the felt. In honor of the Discovery Channel's now-infamous Shark Week guest blogger James Guill breaks down some of poker's biggest-ever donators in a five-part series we've dubbed #WhaleWeek.  Next up: An Old-School Vegas three-pack featuring Major Riddle, Jimmy Chagra and Archie Karas.

By James Guill

From the 1960s to the 1990s, Las Vegas was a true gambler's paradise.

"Old school Vegas" was famous for treating gamblers like kings and whales like gods.

Some of the biggest whales from that era have become part of the allure and legend of Vegas. Below are some of the biggest whales from that era.

Major Riddle

Out of the old school Vegas whales, Major Riddle is considered to be at the top of the list.

Riddle was one of the few businessmen that prospered during the Great Depression, opening a trucking company that became the largest in the Midwest. Part of his success came in part due to his connections with organized crime.

Riddle moved to Las Vegas in 1956 and purchased the Dunes Hotel. Before long he turned the casino into one of the most successful on the Vegas Strip.

While not running his casino he often played high-stakes poker and was a regular loser at the tables. He was often the target of cheating at the table and that helped to compound his losses.

Even when he wasn't being cheated, Riddle's reckless play attributed to many of his losses. Eventually, he began wagering his stake in the Dunes at the tables and in the span of six months lost complete control of the casino.

Rough estimates of Riddle's total losses over his time in Vegas hit about $40 million.

Jimmy Chagra

Jimmy Chagra was one of the most infamous drug dealers in the world during the 1970s. However, due to his deep pockets and tendency to be a great tipper he was welcomed with open arms in Las Vegas.

Chagra was beloved by casinos and those that ran them. He once tipped a croupier $600,000 after a winning session. He tipped $10,000 to a cocktail waitress once just for bringing a bottle of water. He once bailed out a casino with a $10 million loan after players went on a multi-million run.

Chagra was the 1970s equivalent to Andy Beal and high-stakes poker games were often built around him. If you wanted to play against him, you better have a deep bankroll as it took a minimum of $50,000 just to sit at the same table.

Many of Vegas' legendary gamblers grew their bankroll via Chagra's drug money as he seldom walked away from the table a winner. Chagra didn't just lose at poker but also at craps, golf and baccarat.

Chagra's life of crime ultimately caught up to him and he was arrested in 1978 on drug trafficking charges. He was ultimately sentenced to 30 years in prison and remained in prison until 2003. He died in 2008.

Archie Karas

While not the biggest loser in Vegas history Karas is often considered the poster child for degenerate gambling. He's best known as the man that ran $50 up to $40 million and then lost it all and as the player that tested the limits of high-stakes gambling in Las Vegas.

Growing up poor Karas often had to turn to gambling to earn money for food. He ran away from home at age 15 and soon found himself working on a ship for $60 a month. After finding his way to the United States, he moved to Los Angeles and went on his first run as a gambler.

Karas won over $2 million gambling in Los Angeles but lost all but $50 in a high-stakes poker game in 1992. He took that $50 and drove to Las Vegas where he began his first "run."

Over the span of six months, Karas ran $50 up to $17 million playing both poker and billiards. By the end of his initial run poker players quit playing against Karas due to his reputation and the insane stakes that he insisted on.

Karas then switched to playing craps at Binion's Horseshoe where he played for $100,000 a roll. He quickly ran his bankroll up to $40 million and owned all of Binion's $5,000 chips.

What took him months to amass took him just three weeks to lose. He lost $11 million in a single night at the craps table. Shortly afterwards, he played heads-up poker against the late Chip Reese and lost $2 million.

Deciding he needed to change his approach, he decided to switch to high-stakes baccarat. Pushing the casino to raise the stakes even higher, Binion's raised its baccarat stakes to $300,000 a bet. In 10 days, he lost another $17 million.

After losing $30 million, Karas left Vegas to take a break and try to find his mojo but upon his return his loses continued. In less than a month, he dropped all but $1 million of his bankroll and took that to Los Angeles to challenge Johnny Chan in high-stakes poker.

He was able to run that up to $2 million but soon lost that money playing craps and baccarat.

Karas would have several mini-streaks after his $40 million streak but each time he has wound up losing it all back to the casinos. Karas still plays poker tournaments and most recently cashed in the Razz event at the 2013 WSOP.

More of Poker's Biggest Whales:

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