What would you say to a morbidly obese man who can barely walk, yet claims that he can do five sit-ups on the spot? If you happen to be Roger Moore -- the high-stakes poker player, not the actor -- an appropriate response might be, "Wanna bet?"
Moore offered precisely this bet to supersized Doyle Brunson in Las Vegas during a poker game in Caesars Palace's high-stakes arena. Brunson proceeded to complete five sit-ups on the spot and collected his five grand. Later on Brunson was heard to comment, "I'd have bet all my money on that one, but I didn't want to scare the guy off."
You can argue that $5,000 is chump change for high-stakes gamblers who risk that much on a single card without feeling a nervous twitch, but wagers like this one are for more than money. They're called proposition bets and qualify as the crack of wagers, as they provide gamblers with an immediate but short-lasting buzz of action.
Howard Lederer, a professional poker player and a vegetarian who once ate a cheeseburger to win a $10,000 bet that he wouldn't consume meat, sees an intellectual angle to these seemingly degenerate wagers.
"You're trying to figure things out when you make the bets," says Lederer, agreeing that the most impressive props tend to fall into three categories: self-improvement, feats of athletic prowess and goofy things that nobody would normally want to do (one gambler, for instance, spent 48 straight hours in the Vegas go-go bar Crazy Horse, Too). "The fact that nobody has yet figured out whether or not these things can be done is what makes the bets interesting. And it's the satisfaction of winning a bet that makes you want to do it. The amount of money is never enough to impact anybody's lifestyle."
Lederer is hanging out in the Bellagio sport book, sitting amid the big-screen TVs, next door to the poker room, where prop bets are routinely cooked up between hands. Bearded and burly, Lederer describes himself as a "weight bet sucker" (somebody who bets that he can lose weight but never quite manages to stick with the diet). He is far from alone. Pro gambler Russ Hamilton estimates that Brunson, one of the world's greatest poker players and savviest sport bettors, has lost upwards of $3 million on weight wagers. "The bets always start off really well, then you lose a big pot in poker and order a pizza," says Hamilton, who's been in that situation, too. "Making a $50,000 weight bet with Doyle Brunson is the best bet you can ever make in your life. But you have to be careful who you bet with. You need to make these bets with people who don't care about the money. Some guys will cut off their arms to win a $50,000 bet."
While weight bets tend to be long shots for gamblers with girth, there are other wagers for which a hefty physique can be beneficial, as it was for Brunson with the sit-up challenge. Lederer certainly used size to his favor when Huck Seed claimed he could beat him, hopping on one foot, in a 50-yard dash. The fact that Seed, a former World Series of Poker champion, had already proven himself to be extremely athletic (via a wide range of other prop bets) didn't bother Lederer one bit. After watching Lederer do a preliminary run, Seed realized that he could never win on one foot and paid off the $5,000 bet.
But that's OK, because he got back at Lederer with another bet, one involving a back flip. "Huck beat me out of $10,000 on that one," says Lederer. "He's 6 feet, 6 inches tall and had to do a standing back flip. He had to start flat on his feet, jump over, and land on his feet backwards. That was the bet. Apparently his father or his uncle was an acrobat, and Huck learned to do it with a harness, jumping into a pool or something." Lederer's voice is full of admiration, sounding as though he figures that Seed earned the money and deserves it. "Huck takes pride in the physical stuff. He's a talented guy."
Asked to comment on his seemingly uncanny skills as a prop bettor, Seed shrugs them off, insisting, "People think I win a lot more of these proposition bets than I really do." Even though Seed lost a "beard" bet (he had to spend a year not shaving, but needed to when there was a death in the family) and an "ocean" bet (fellow poker player Phil Hellmuth bet him $50,000 that he could not stand up to his shoulders in the ocean for 18 hours. Seed lasted three before paying off), Lederer is skeptical about Seed's purported mediocrity. "Huck has been struggling a little bit in poker, but he has not been struggling in proposition bets."
Maybe Lederer's opinion stems from Seed's having won what most of us would deem an impossibly challenging bet. With many thousands of dollars at stake, he had to play a desert golf course four times in a single day and break 100 on each round while using only a 5-iron, a sand wedge and a putter. "The guy making the bet was able to choose the day, and he selected a day when the temperature was up to 120 degrees," remembers Lederer, adding that Seed had to play without the benefit of a cart -- he had to run the course to complete all the holes. "He shot a 100 on his first round at 6 in the morning. So at 8:30 he still had to shoot four more rounds." More incredible than Seed's winning the bet is that he improved with each round. As Seed put it at the time, "I really got into a groove with the 5."
The opportunity to find that unlikely groove while simultaneously doing something spectacular and generating action all contribute to the appeal of these wagers. After all, if it was only about money, well, Vegas abounds with surer bets. "Prop bets are recreation for these guys," says Richard W. Munchkin, author of Gambling Wizards: Conversations with the World's Greatest Professional Gamblers. "When they play the games that they play professionally, it's not really gambling. This is. I remember hearing a story from Mike Svobodny [a top-ranked backgammon player], who had made a tennis bet with Huck. Mike's a better player and Huck vowed to practice eight hours a day in order to beat him. Upon hearing that, Mike immediately bet Huck that he couldn't practice for eight hours a day. At the end of the month, Huck had made his eight hours a day for the practice bet, but lost the game bet anyway."
An innovative master of the proposition bet-which is probably as old as gambling itself -- was the great Titanic Thompson, a scratch golfer who'd beat somebody as a righty, then offer to play a double-or-nothing round with his left hand, presumably as a concession (Thompson always neglected to mention that he was a natural lefty). After betting a group of golfers that he could hit a golf ball 500 yards, Thompson drove to a frozen lake near Chicago to accomplish the seemingly impossible task by skidding the ball across the ice.
Decades later, in the mid-1960s, proposition master "Amarillo Slim" Preston taught himself to play with a hammer instead of a golf club, and he's beaten pros by using a bow and arrow instead of a club and balls. During a memorable match at Las Vegas Country Club, he accepted a bet against famed hustler Lee Crump, who was sure that he could hit the roof of the distant Hilton Hotel with a golf ball (Crump played himself on that one and Slim won the wager).
Puggy Pearson, the aged hustler who spent his golden years beating men half his age at all kinds of golf bets (some of which were actually on the square), devoted years of his youth to perfecting the kinds of trick shots that can turn pool rooms into prop-betting gold mines. "Pride and ego is what I take advantage of when laying down a prop bet, especially against the young whippersnappers," drawls Pearson, who's lauded as one of the world's great intuitive gamblers. "You figure out what somebody thinks you can't do, even though you know you can. Then you find a guy with a swelled head and take advantage."
Following Pearson's line of thinking, the best victims with whom to make proposition bets are ex-jocks, the kinds of men who used to be good at a sport, haven't played in a while, and now have no real idea how badly their games have deteriorated. Such was the case when a once talented bowler, who'd been away from the sport for 15 years, told Russ Hamilton that he could break 190 in three out of three games. "He said he could do it for $1,000 per game," remembers Hamilton, who at the time had been participating in a poker tournament at the Orleans Casino, which, conveniently, has a 24-hour bowling alley on the premises. "He wanted to go home and find his ball, but I wanted to do the bet right away; I knew it would be impossible for him to make that score after 15 years away from the lanes. He said he needed a bowling ball, so we went to the alley and I had the pro drill one for him. He didn't want to rent shoes, so I bought him a pair. It cost me $300 to get this guy started, but I swept all three games for $3,000. By the time I left, he was hungry to get even and there were some pythons waiting there to gamble with him."
Sometimes the bets are too good to pass up -- such as when Doyle Brunson swore that The Shawshank Redemption had won the Oscar for Best Picture in 1995 and Howard Lederer knew that the guy's poor listening skills would have made it almost impossible for him to remember the winning film (Forrest Gump took the prize that year) and other times they're too good to take. "John Hennigan [a top poker pro] bet that he could live for six weeks in Des Moines, Iowa," remembers Lederer. "He was going to go there to work on his golf game. But he's such an action junky that he wound up lasting two days. The way these bets work, he could have stayed there for 10 days and called the people who had bet against him. At that point he could have told them, 'Look, I'm gonna do it, but I don't want to do it. Let's settle.' Maybe he could have gotten them to buy him out of the bet for a discount. But that's not going to happen after two days. I knew he had no chance of staying in Des Moines, and I didn't want to be the bad guy who refuses to settle and forces him to stay there."
Outrageous and high-flying as some of today's proposition wagers may be -- a single golf prop at La Costa, in San Diego, for instance, had $500,000 riding on it -- none holds a candle for sheer gutsiness to a bet accepted by the late poker legend Johnny Moss during the prime of his hell-raising, hard-drinking life. "Moss was at a bar where one of the regulars was known for being the toughest fighter around," relates Lederer. "He was 100-and-0 in bar fights and was huge. A gambler laid Moss $15,000 to $1,000 that Moss couldn't beat up this guy, with the condition that Moss would get in the first shot. Of course, this tough guy had no idea he was part of a bet, and Moss cold-cocked him from behind. But don't worry, Moss ended up in the hospital for two weeks, with broken bones, completely laid up and close to death. Puggy Pearson showed up at the hospital and told Moss he was crazy, that he couldn't go on taking these kinds of bets." Moss, a true gambler, up for any proposition as long as the price was right, looked at Pearson and murmured, "Fifteen-to-one was too good to pass up. I had to take it."
Whether or not Pearson's admonishment ignited a fresh round of betting is unclear, but, knowing these guys, hardly unlikely.
Michael Kaplan writes frequently about gambling for Cigar Aficionado.
Log in if you're already registered.
Search our database of more than 17,000 cigar tasting notes by score, brand, country, size, price range, year, wrapper and more, plus add your favorites to your Personal Humidor.