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Betting (and Booking) Backgammon in Monte Carlo

It’s one of the oldest games in the world. How easy is it to get rich off it?

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Gamblers is a podcast about men and women who live by their wits and wagers. People who bet big on themselves, and won. From golf and chess hustlers to a Super Bowl handicapper, Season 2 focuses on the fascinating lives of professional underground gamblers and how they make their money.

I’ve come to Monaco for the Backgammon World Championship, which has been held here for the past 42 years. It’s an event that attracts players from around the globe—an international gathering of elite games players, wealthy hobbyists, and shark-toothed hustlers. For six days, nearly 200 players will compete in a double-elimination tournament to win the title of world champion and the first prize of 50,000 euros.

I’m here with Alex Lehmann and Sander Lylloff, two professional gamblers who are not only trying to win the world championship, but also to book it.

Alex and Sander will set a price on every remaining player each day, and they’ll take any bets from anyone who wants action.

The buy-in for the World Championship is 1,000 euros, a relatively modest sum. The real money is found in side action—i.e., money games played at night after the tournament rounds wrap up.

But it still helps to have a little extra motivation in the tournament, so for years players would bet on themselves—either with a bookmaker, or through a calcutta auction tournament organizers held every year—to make their potential prize a bit more lucrative.

This year, Alex has volunteered to book the tournament, something he’s done in the past. It’s a significant undertaking. Taking bets on all the players requires a big bankroll, not to mention lots of guts. After all, even if they shade the odds in their favor, the house isn’t necessarily guaranteed to win.

Alex Lehmann is a high-stakes gambler from New York, though today he and his family live in Portugal. He was introduced to gambling by a fellow chess player he met in college in Buffalo, Matvey Natanzon, who before his passing in 2020 was better known in these circles as “Falafel.”

Backgammon wasn’t like chess. You could make real money playing backgammon, and Alex did. He went from playing for a couple of bucks a game in Washington Square Park to finding wealthy marks who would play for thousands of dollars a game, like the French entrepreneur Marc Armand Rousso, who was known in the gambling world as “The Crocodile.”

Alex went on to earn millions gambling on all sorts of games, but especially poker, where he made a ton of money grinding online during the early days of the poker boom. After a while, he realized playing poker was mostly mechanical. He trained himself to make the same plays over and over.

So he developed bots to play for him. And they won. A lot. He started hiring people, built his robot empire into a company, and cleaned up.

Sander Lylloff is a 40-year-old professional gambler from Copenhagen. Like Alex, he plays a lot of games, and plays them well.

He’s made nearly $2 million playing poker, including winning a 2007 European Poker Tour Main Event.

Today, Sander still earns much of his living as a sports bettor, mainly on soccer.

“If I have to pick a thing on earth that I’m best at, it’s not sports betting,” he says. “It’s not trading; it’s not cooking; it’s not making love; it’s not being a good dad. It’s playing backgammon.”

And also like Alex, Sander isn’t here to win the World Championship of Backgammon.

“Whoever wins the World Championship, I’m happy to play them for whatever they won. That’s the way I think about it.”

For a player as good and as well known as Sander, it’s increasingly difficult to find a good money game. He has to cast a pretty wide net to catch fish these days.

Hopefully there will be people here in Monte Carlo who have enough gamble in them to make a game with Sander and give him some action. If not, maybe bookmaking will provide some extra scratch.

But taking bets on the winners—and playing in the event— presents an interesting conundrum.

To hear the full backgammon episode, click here. This is the final episode of Season 2 of Gamblers; prior episodes are available on Spotify. This excerpt has been lightly edited for clarity and length.