The Grass is Always Greener

Thirty days in Des Moines

During the 1990s, John Hennigan, an eccentric gambler who had been making a living by his wits and skills in poker and pool for several years, moved from Philadelphia to Las Vegas. His reputation and nickname, “Johnny World,” preceded him, due to his already exceptional skills and willingness to bet on anything. By the time of Duke’s account, he was a legendarily successful player in high-stakes games, and in major poker tournaments had earned four World Series of Poker bracelets, a World Poker Tour championship, and more than $6.5 million in prize money.

John was a perfect match for Las Vegas. He arrived already in rhythm with the town: sleeping all day and spending all night in poker games, pool halls, bars, and restaurants with adventurous, like-minded peers. He quickly found a group of professional gamblers with similar interests, many from the East Coast.

Although John and Vegas seemed made for each other, he had a love-hate relationship with the lifestyle. Playing poker for a living has the allure of giving you the freedom to make your own schedule but, once it boils down to your per-hour net advantage, you are tethered to putting in the hours. You’re “free” to play or not play whenever you want, but you can feel compelled to punch a clock. Worse, the best games are at night, so you’re working the graveyard shift. You get out of rhythm with the rest of the world, never see the sun, and your workplace is a smoke-filled room where you can’t even see outside. John felt this keenly.

One night, John was in a high-stakes poker game and the talk between hands somehow included the state capital of Iowa, Des Moines. John had never been there or seen much of the Midwest, so he was curious about what life in Des Moines might be like—a “normal” life that increasingly seemed foreign to him, waking up in the morning and living in the daylight hours. This led to some good-natured ribbing as the other players in the game imagined the prospect of a nocturnal action junkie like John in a place that seemed, to them at least, like the opposite of Las Vegas: “There’s no gambling action.” “The bars close early.” “You’d hate it there.” Over the course of the evening, the discussion shifted to whether Hennigan could even live in such an unfamiliar place.

As is often the case with poker players, a conversation about a hypothetical turned into an opportunity to propose a wager. What would the stakes have to be for Hennigan to get up from the table, catch a flight, and relocate to Des Moines? If he took such a bet, how long would he have to live there?

John and the others landed on a month in Des Moines—a real commitment but not a permanent exile. When he seemed willing to, literally, walk out of a poker game and move 1,500 miles to a place he had never been, the other players added a diabolical condition to the negotiation: he would have to confine himself to one street in Des Moines, a street with a single hotel, restaurant, and bar, where everything closed at 10 p.m. That enforced idleness would be a challenge for anyone, regardless of the location. But for someone like John, a young, single, high-stakes gambler, this might actually count as torture. John said he would take such a challenge if they made one concession: he could practice and play at a nearby golf course.

After agreeing on the conditions, they still had to negotiate the size of the bet. The other players needed a number that was large enough to entice John to accept the wager, but not so large that it would entice John to stay even if he really hated it in Iowa. As one of the most successful cash-game players in Las Vegas, a month in Des Moines could cost John, potentially, six figures. On the other hand, if they offered him too large of an upside to stay in Des Moines, he would certainly endure the discomfort and boredom.

They settled on $30,000.

John considered two distinct and mutually exclusive alternatives: taking the bet or not taking the bet. Each came with new risks and new reward potentials. He could win or lose $30,000 if he took the bet (or win or lose greater dollar amounts at the poker table if he turned it down). He could also benefit from the decision to move to Des Moines long after the bet was over, if he used the golf-practice time to improve his chances gambling at high-stakes golf. He could further his reputation of being willing to bet on anything and being capable of anything, a profitable asset for professional gamblers. He also had to think about the other, less quantifiable things he might value. How much might he like the pace of life? How would he value taking a break from the action? Would he become more relaxed experiencing the more traditional schedule? Was the break worth it to take the big pay cut from not being able to play poker for a month? And then there were the real unknowns. He might just meet the love of his life on that one street in Iowa. He had to weigh all of this against the opportunity costs of leaving Vegas—money from lost earning opportunities, nights missing doing the things he enjoyed, and even perhaps missing meeting the love of his life at the Mirage during that month.

Johnny World moved to Des Moines.

Was a month of detox away from the nightly life of a high-stakes Vegas pro going to be a blessing or a curse?

It took just two days for him to realize that it was a curse. From his hotel room in Des Moines, John called one of his friends on the other side of the bet and tried to negotiate a settlement. Just as parties in commercial lawsuits often settle before trial, in the gambling world negotiated settlements are common. What was particularly funny about John’s call was that his opening offer was that the others pay him $15,000 to spare them the cost and indignity of losing the whole amount. He argued that since he was already in Des Moines, he was clearly capable of waiting out the month to get the full amount.

The other bettors, literally, were not buying it. After all, John made this offer after only two days. That was a pretty strong signal that not only would they likely win the bet, but they might earn a return (in fun) by needling John while he served out his sentence.

Within a few days, John agreed to pay $15,000 to get out of the bet and return to Vegas. John discovered, in spectacular fashion, that the grass in Des Moines wasn’t greener for him.