Jackpot (or Not)! Vegas' biggest losers and winners

Las Vegas winners and losers

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On March 21, 2003, a 25-year-old software engineer from Los Angeles won the record Megabucks jackpot of $39.7 million. He didn't make his name public, so there's nothing to go on but news reports and the recollections of people who witnessed the big win at the Excalibur Hotel and Casino. But whoever he was, people still flock to Las Vegas in the hopes of recreating whatever strange magic he performed that day.

The overwhelming majority of people following this dream will have it smashed, and leave with less money than they had when they came in. But despite facing steep odds that all but guarantee coming out a loser, every one of these gamblers dream that somehow, they will crack the code and walk out a winner with a life-altering sum of money stuffed into their bulging, overflowing pockets.

CNBC.com presents a list of 10 people who made it big or lost it all in Las Vegas, and a few who did both.

—By CNBC's Daniel Bukszpan
Posted April 30, 2014

"Money Talks" takes viewers inside the world of Steve Stevens, a sports handicapper who runs VIP Sports out of Las Vegas. Wednesdays at 10 p.m. ET/PT.

Archie Karas

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Archie Karas is a gambler who made his way into the annals of Las Vegas history. According to a 2008 article in the online poker publication Bluff, he spent three months in 1993 playing against poker's best at legendary casinos such as Binion's Gambling Hall and Hotel (pictured), eventually turning $7 million into $17 million in a streak known to aficionados as "The Run." Unfortunately, his skill at winning money was matched by his knack for losing it.

According to CNN, he won $40 million during a three-year period in the 1990s, all of which he lost in three weeks. In September 2013, he was arrested at his home in Las Vegas on allegations that he had marked cards in a San Diego blackjack game two months earlier, according to Reuters. In October 2013, he pleaded not guilty to burglary, winning by fraudulent means and cheating at a blackjack table.

Terrance Watanabe

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In 2007, Terrance Watanabe embarked on what the Wall Street Journal called "a year-long gambling binge," in which he lost nearly $127 million at the Caesars Palace (pictured) and Rio casinos. According to the Journal, this amount accounted for 5.6 percent of the Las Vegas gambling revenue of Harrah's Entertainment, the casinos' parent company.

He was indicted by a grand jury for failing to repay the casinos $14.7 million that had been extended to him as credit, according to the Associated Press. In an interesting turn of events, he filed a civil lawsuit against Harrah's Entertainment on the grounds that casino employees allegedly kept him drunk and hopped up on painkillers in order to keep him gambling, according to the Las Vegas Review-Journal. The parties settled out of court on March 7, 2013 .

Alexander Degenhardt

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Alexander Degenhardt was a U.S. Marine who put $100 into the Money Vault Millionaires Seven slot machine at the Bellagio (pictured) on Feb. 19, 2012. He instantly became $2.9 million richer, and he credits his decision to become a bone marrow donor for the windfall.

"I look at this as kind of good karma for that," he said. According to the Sun, his karma is good for $100,000 annually over the course of 20 years, and his first plan for the money was to help his mother and his pregnant sister with their bills.

Omar Siddiqui

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Omar Siddiqui was vice president of Fry's, a consumer electronics retailer, and a frequent visitor of such Las Vegas casinos as the MGM Grand (pictured). He lived the life of a high roller when he was there, but it all fell apart on Dec. 19, 2008, when he was arrested at and accused of embezzling $65 million. The money was earmarked to help pay off gargantuan gambling debts he had racked up.

According to the Los Angeles Times, he lost approximately $167 million over the course of a decade, including losing $8 million in a single day. In July 2011, he filed for Chapter 7 bankruptcy protection, citing $137 million in debt, which included $22 million to multiple casinos, according to the San Jose Mercury News. In December 2011, he was sentenced to six years in prison after pleading guilty to one count of money laundering and one count of wire fraud.

Joe Francis

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"Girls Gone Wild" founder Joe Francis built an empire by filming female college students baring their breasts during spring break. He also lost $19 million in Las Vegas without actually gambling it away. He claimed that casino owner Steve Wynn had threatened to kill him over a gambling debt, so the mogul hauled him into court and won his slander case on Sep. 9, 2012, to the tune of $20 million, according to the Associated Press.

The next day, the same jury ordered Francis to pay an additional $20 million in punitive damages. However, two months later, Los Angeles Superior Court Judge Joanne O'Donnell cut $21 million from the total award of $40 million, leaving Francis a mere $19 million in debt.

Elmer Sherwin

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In 1989, Elmer Sherwin won a Megabucks jackpot of $4.6 million at the Mirage. On Sep. 15, 2005, at the age of 92, he hit it again at North Las Vegas' Cannery Casino (pictured). That jackpot was good for $21.1 million, and according to the Las Vegas Sun, it made him the first person ever to win Megabucks twice.

The second victory was not an accident. Sherwin had pursued it doggedly ever since the first one, but he told KLAS-TV that money was never his motivation. "I was after the prestige of hitting it twice," he said. "'Cause I knew no one has done it… I just kept after it both times."

"Nick the Greek" Dandolos

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"Nick the Greek" Dandolos was a legendary gambler who played against another famous high roller, Johnny Moss, in what many believe to be the game that inspired the World Series of Poker. Set up by casino owner Benny Binion in 1949, the marathon game was open to the public and meant to generate publicity for his Horseshoe Casino (pictured).

According to the poker publication Bluff, the game lasted for five months and comprised sessions of four or five days, with pauses only for the players to sleep. Other players were allowed to get in on the game, provided they had $10,000 to buy in. But none of them lasted long against the two masters, and the pot eventually grew to $500,000.

The game ended with Dandolos $2 million in the hole. According to poker lore, he stood up and said, "Mr. Moss, I have to let you go." And with that, his loss went down in gambling history.

Cynthia Jay-Brennan

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On Jan. 26, 2000, cocktail waitress Cynthia Jay-Brennan played the Megabucks machine at the Desert Inn in Paradise, Nevada. According to the Las Vegas Sun, she won almost $35 million, one of the biggest jackpots on record. But sadly, she barely had time to enjoy it.

On Mar. 11, 2000, her car was rear-ended by a drunk driver, leaving her quadriplegic and killing her sister, who was a passenger. According to the Las Vegas Sun, the driver, Clark Morse, was found guilty of involuntary manslaughter, driving under the influence and leaving the scene of an accident, among other charges. He was sentenced to 28 to 92 years in prison.

Stu Ungar

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The late Stu Ungar is considered by many to be one of the greatest poker players who ever lived. According to New York magazine, he was called "the Mozart of the card table," and he is still remembered as one of the all-time greats to this day.

The New York Times said that over the course of his gambling career, he won—and lost—$30 million at such venues as the Lady Luck Hotel and Casino (pictured), but his ultimate downfall wasn't gambling. It was cocaine, "which steadily grew into a profound addiction."

He died of a heart attack on Nov. 22, 1998 at the age of 45, and despite the large sums of money that had once passed through his hands, he was so destitute at the time of his death that his friend Bob Stupak, a casino owner and fellow gambler, was forced to take up a collection at the funeral in order to pay for it, according to the book "One of a Kind: The Rise and Fall of Stuey, 'The Kid', Ungar, The World's Greatest Poker Player."

Zhenli Ye Gon

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Zhenli Ye Gon was a businessman from Shanghai who ran the Mexican pharmaceutical company Unimed. According to the Washington Post, he had lost almost $126 million in such Las Vegas casinos as the Mirage (pictured) while living in the U.S.

The Post's source for this figure was none other than the U.S. Drug Enforcement Agency. The DEA was investigating allegations made by Mexican authorities that his company was a front for drug cartels, and that it illegally brought chemicals into Mexico to produce methamphetamine, which was to be sold in the U.S. However, the case against him in the U.S. was dismissed with prejudice in June 2009.

Money Talks

"Money Talks" takes viewers inside the world of Steve Stevens, a sports handicapper who runs VIP Sports out of Las Vegas. The one-hour docu-soap follows Stevens and his stable of agents who sell their picks to gamblers looking for any kind of edge. From small-time bettors who will lay out a few hundred to the whales who put six figures on the line, this is a world built on high risk, high reward and high emotions. In a city of distractions and every imaginable vice, Stevens needs to keep his agents focused on building new business while entertaining big-time bettors who come to Vegas with big bankrolls and even bigger expectations.