Interesting Characters Have Made Interesting Bets Over The Years

Interesting characters have made interesting bets over the years. Were they risking it all, or was there method in their maneuvers?

Tales of those who have wagered high and won intrigue all who know the thrill of raking in the money after testing their skill and luck at a game. And whether we're envious or relieved that it wasn't us, the stories never fail to impress.

An exact science

In 1873 Joseph Jaggers spent days at a Monte Carlo casino writing down every number that came up on the roulette wheels, hoping to spot a trend. After a while he walked away with $450,000. Not bad for a few days' work back then. Jaggers, a British engineer, had noticed that cotton mills began to wear down after long periods of use and soon realized that roulette wheels would probably do the same. He figured that once that happened each wheel would have developed its own balance that favored certain numbers. By painstakingly scruti-nizing each wheel at the casino, he worked out which numbers came up most frequently on one of them.

He made $300,000 before the casino noticed something was amiss and had the wheel moved. Jaggers lost a small fortune before he realized this. Finding it again he quickly added to his winnings before the casino modified the wheel and reset the balance. It would have been strange watching someone betting on the same numbers, spin after spin, but Jaggers took the gamble and went down in history as one of the men who broke the bank at Monte Carlo.

What goes around comes around

In the early 1980s Toronto banker Brian Molony lost millions in an incredible gambling spree that lasted 18 months. The kicker was that if he'd known when to cut his losses, Molony would have been a wealthy man today. In 1982 the 24-year-old placed $5,000 on each outcome of 40 different college football games and lost all his money. Then he staged a dramatic recovery and put $500,000 down on the Super Bowl and won. Over the next year and a half, however, Molony lost over $10 million dollars - all the money he had stolen from the Canadian Imperial Bank of Commerce.

Super sevens

William Lee Bergstrom (the "Suitcase Man") has pride of place in the annals of famous wagers. Legend has it that in 1980 Bergstrom asked if he could place a $1 million bet at the craps table. Bergstrom went to raise the money and arrived a short while later with a suitcase containing $777,000, apologizing because it was all he could raise. He bet it all at once on the Don't Pass line. He was so optimistic he could win that he brought along another suitcase for his winnings. Supposedly the shooter that Bergstrom bet on "sevened out" in three throws and he left Binion's with $1.5 million.

A really good year

Australian media mogul Kerry Packer reportedly won over $25 million playing blackjack at the MGM Grand in 1995. Packer was apparently playing between six and eight hands simultaneously, betting $200,000 and upward a hand when he made the small fortune. And he did it all in 40 minutes. According to one eyewitness, Packer was actually down to start off with but then surged ahead to over $30 million before losing $5 million and calling it quits. On leaving the floor he tipped each of the 40 people on shift $2,500.

The beautiful game

Well-known hotelier Bob Stupak has made his fair share of notable bets. In 1989 he made the largest wager in Nevada history betting on the Super Bowl between the Cincinnati Bengals and the San Francisco 49ers. He won $1 million on the game. A decade earlier Stupak had made another extravagant bet with the incredible card-player Stu Ungar. Stupak bet Un-gar $100,000 that he wouldn't be able to count down the last three decks in a six-deck shoe. Ungar called out every one of the 156 cards correctly. Stupak later said of Ungar, "He was the best. You can't expand on that."

Blackjack for a cause

For a publicity stunt in 2001 Howard Stern wanted to lay down $1 million on a single hand of blackjack. There were no takers among the casinos and Stern's much-hyped-about bet was shrunk to an anticlimactic $100,000. Despite losing $800 during one session at the blackjack tables, Stern's luck held when it counted, and he won the bet. Stern didn't pocket the money. Instead the winnings went to a charitable cause.

The poker people vs. Larry Flynt

It cost Larry Flynt $2 million when he challenged Amarillo Slim to find out who was the better man at poker. Flynt, founder of Hustler magazine, also reportedly lost $5 million to Stu Ungar in a series of poker matches. Don't write Flynt off just yet though. When he's having a good day he's reported to be one helluva card player.

When horse sense pays big

Arnold Rothstein may be best remembered for fixing the 1919 World Series, but he also won a lot of money fair and square. In 1917 he tried to place a hefty $240,000 bet down at the tracks on a horse named Hourless, but couldn't find anyone willing to take him on. A few days before the race Rothstein got a call informing that whatever bet he put down, regardless of the amount, there was someone willing to take him up on it. Rothstein smelled a rat and got the horse's owner to change jockeys at the last minute. Hourless won convincingly and Rothstein earned a cool $300,000.

He earned over double that a few years later when he bet on his own horse, Sidereal. It was a last-minute decision to race him and, not wanting to appear too conspicuous, he used 40 track men to place bets for him. Rothstein almost lost everything when it looked as if Sidereal wouldn't arrive at the track on time, but he arrived with six seconds to spare. Sidereal raced, won, and Rothstein earned $850,000.

The Midas touch

He's been called the luckiest man alive for turning a borrowed bankroll of $10,000 into a $17 million winning streak. Archie Karas, a Greek immigrant, first arrived in Vegas in 1992 with just $50 in his pocket. He managed to borrow a $10,000 stake and headed straight to the poker tables. What followed was what people now fondly refer to as "The Run." Karas quickly doubled his money, paid back his benefactor, then won over $1 million in just a few short hours. From there Karas headed to Binion's Horseshoe and, over six months, played winning hand after winning hand of poker. When he ran out of people to beat at poker, he gathered his chips and went for the craps tables, winning millions of dollars more. Karas enjoyed winning sessions of as much as $4 million at the table, and at one point was said to have all of the Horsehoe's chocolate-colored $5,000 chips - over $11 million worth. By the time his run ended he had a pot of over $17 million.