5 Rogues Who Gambled Their Way To Glory

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by Steven Assarian

Gambling is a game of chance — that’s what makes it so fun. Luck shines its beautiful face upon you and you walk away from the table with money to splurge on things nobody ever needs. But sometimes, probability isn’t the only factor, and sheer badassery plays an important role in you finally being able to afford that Batmobile.


Overweight, Depressed Teen Makes Half A Million In 5 Years By Pool Hustling

Danny Basavich was an overweight, depressed kid who didn’t have a ton going for him. What the world didn’t know was that he was kind of like Daniel LaRusso, hiding a great talent that was only a montage away. But instead of Crane kicks, he had an arguably more badass talent: pool, the game we all think we’re good at until we actually start to play it.

He honed his skills at a pool hall by his house, and at 17, he went and beat a neighborhood pool shark with the moniker “Kid Vicious.” Because of his weight, they started calling him “Kid Delicious,” and the name stuck.

Because this clearly is a movie script and not real life, he partnered with another hustler, “Bristol Bob” and an informant they called “007” who looked for pool halls with talent ripe for the hustling. On 007’s tips, Basavich traveled the country taking down arrogant, light-weight pool players by playing up his weight and his aw-shucks manner. On college campuses, he’d act like a dumb freshman who was ready to put a few hundred dollars down on a piece of this new-fangled “pool.” He would even buy merch from the town college and spill cake on it, convincing the bros at the pool halls that he was a whale ready for the taking.



“So you guys play by nacho rules, right?”

What’s all the more impressive is that Basavich had his run at a time when the Internet made hustling an even harder game to win, because people started talking on forums about this crazy good fat kid who was taking them for all their money while being just the nicest guy about it. Before the rumors caught up with him, he won half a million dollars in a little over five years by following the money (and running from the danger) of pool hustling all around the country.

Once that money train stopped, he made a name for himself on the pro circuit, like the bootleggers that went into beer distribution. He also had a bestselling book written about his life as “the last great American pool hustler.” You know if they wrote a book about our lives, we wouldn’t be the last American anything, let alone someone whose life was basically the Color of Money.

Bill Benter Was So Good At Gambling, He Once Turned Down $13 Million In Winnings

Bill Benter is the personification of the phrase “if you’re so smart, why aren’t you rich?” In particular, if all these statistic experts are able to predict the future, why not put their skills to use in, say, sports betting, where you could make all the money? But that’s exactly what Benter did. His first love was with the book Beat the Dealer, which detailed how to play blackjack mathematically. Once that well dried up (read: the casinos got tired of being cleaned out) he fell in love with the academic paper about handicap horse racing.

He ended up flying to Hong Kong to start betting on horse racing, using computer assisted betting. His statistical system, which was the first to deal with horse betting as a mathematical problem, made him a millionaire many times over, including winning the Triple Trio, a type of bet that a seventh of the Hong Kong population gambles on. Winning was a 1 in ten million shot, represented a $13 million payday, and he never even cashed it out because it would’ve been “unsporting.” Of course, he didn’t need the cash, because he’d already won a cool billion (not a typo -- it’s the “b” one) over the years. It’s one thing to win a ton of money; it’s quite another to win so much that you can turn down $13 million and not even feel it.



His cat had more than enough.

Benter has taught himself to be one of the greatest sports bettors in history. He’s so good that he’s currently a professor who teaches PhD students how to be stats nerds, and he wrote a series of academic papers explaining his statistics system. Oh, and with all that cash, he now runs a foundation out of Pittsburgh, donating to social and political causes, like eradicating polio and making us all feel a little bit worse about our life choices.

Nick Dandolos Became Rich And Went Broke 73 Times In His Life

Nick Dandolos, or “Nick the Greek” because Casino was a documentary, was everything you’d want in a sophisticated gambler: he spoke five languages, quoted philosophy, and he was damn good at his work. He started out as an immigrant from Izmir, gambling on the small allowances that his parents would send him when he went to the States to make his fortune. And boy, did it turn into a lot.

He won and lost five hundred million dollars over his lifetime. He became rich and went broke 73 times, which you might think is a very specific number ... but more importantly, how did he do it? Well, first he bet on everything, from horse racing to craps to faro, an old school game that people liked to play in the Old West, and won like crazy. In fact, he won his first million on horses before he was 20 years old. He also reportedly gave away millions in his lifetime and handed out money to anybody who asked, like a cool Greek Santa Claus.

In his day, his exploits made him a romantic figure, quoting Plato and Aristotle and showing Richard Feynman around statistical analysis (read: making Richard Feynman even more awesome). It’s even reported that he showed Albert Einstein around his casino haunts, calling him “Little Al from Princeton and telling his friends that “Al” controlled “a lot of action in Jersey,” which, while not confirmed, is the most perfect movie idea we’ve ever heard.



“Hey guys! Meet my buddy Al … Smith.”

Naturally, his exploits made him famous, and casinos being casinos, wanted to cash in on his fame. That’s what led him to play a five month poker marathon with a fellow gambler named Johnny Moss. The casino owner, who was a friend of Dandelos’s, decided to have them play in the lobby of the casino -- a couple of poker geniuses making the game look good. But he probably didn’t contend on them sticking around for five months, stopping only to sleep ... otherwise, they played poker constantly.

Dandelos, though, wasn’t only famous for winning, he was also famous for losing, because in this poker marathon, Moss was able to get him $2-4 million in the hole before finally, Dandelos threw in the towel, uttering the famous poker maxim: “Mr. Moss, I have to let you go.” It was so epic, it was the inspiration for the World Series of Poker.

He also said: “The next best thing to gambling and winning is gambling and losing.” No wonder he was one of the first gamblers enshrined in the Poker Hall of Fame.

“Poker Alice” Tubbs Cleans Out The Whole Old West

Speaking of awesome quotes, one of the best gambling quotes of all time came from a gambler in the Old West: “Praise the Lord and place your bets, I’ll take your money with no regrets,” which sounds way more fun than Sunday school. The mind behind the words was “Poker Alice” Tubbs, a legend in the Old West and one of the greatest gamblers in history. When her husband was killed in a mining accident, the widow Tubbs took her poker skills from town to town, cleaning out people who thought they could beat her and her legendary poker skills. She also carried a .38 and didn’t hesitate to use it when the situation warranted.

The thing is, Tubbs never cheated. She was brilliant at counting cards, playing the odds, and using her unusually good looks in a lonesome West in her favor. That, and a general disrespect for her skills kept the young guys coming and ready to be fleeced. One dealer explained to her that faro was a man’s game and told her not to cry when she lost to him. At the end of the night, he was out everything, with a “hole in his pocket big as a stove-pipe,” the sickest burn in the West. It’s reported that Tubbs won a quarter of a million dollars, which today would roughly amount to all of the money, through her gambling exploits.

Plus all of the sweet cigars that money could buy.

Not content to sit around smoking cigars, she parlayed that cash into a gambling house and brothel; a business that she was willing to defend, uh, rather spiritedly. When one group of young soldiers came in hootin’ and hollerin’, Tubbs came out shooting with a .22, wounding one man and killing another. She wasn’t charged with the shooting, but she was charged with running a house of ill-repute. The charges didn’t stick, especially when you get a pardon from the governor of the state, because everybody was cooler with brothels back then, we guess.

Alvin “Titanic” Thompson Was Unbeatable In Everything He Did

You know you’re a legend when you give yourself a nickname like “Titanic Thompson”, and everyone is just kind of cool with it. He was one of the most famous proposition gamblers in history, which means betting on everything he could think of, from being able to toss a key into a hotel’s pigeonhole to score a free room, to throwing a lemon over a building which won him the respect, and presumably the money, of none other than Al Capone.

What Capone didn’t know at the time was that Thompson was also a con man on the side; he’d filled a lemon with buckshot the night before. He also did the same thing with a walnut, stuffing it full of lead so that it would go further than anyone believed it would. He also killed five men, which is par for the course when you’re running with Al Capone.

His best bets, however, were on the links. In the days when Ben Hogan was making headlines for ten grand a year, Thompson was betting $20,000 a hole. He beat the greats of his day, including Hogan, who called him “the best shotmaker I ever saw ... Right- or left-handed, you can’t beat him.” He also made putts with magnetized golf balls, and won a bet that he could drive a ball 500 yards by doing so on a frozen lake, his side hustle as a con man still in full effect.



“Right, so, that was your house. Double or nothing?”

When he wasn’t cleaning house on the greens, he was doing it on pool tables. At one point, he teamed up with “Minnesota Fats” Wanderone, who taught him the art of pool sharking. They then toured the country, vacuuming the cash from suckers’ pockets and using Thompson’s wit (and shotgun) to escape their ... um ... displeased victims.

His legend was so big as a gambler that he was the inspiration for the character Sky Masterson in the musical Guys and Dolls. To be honest, the real story is way, way better, even if it wasn’t a musical.

Like this article? Check out “5 People Who Took Con Artistry To Crazy New Heights” and “5 Ridiculous Cybercrimes You’ll Be Amazed Were Pulled Off”.

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