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’m at a private golf course in Las Vegas called TPC Summerlin. It’s in the middle of the desert, but like a lot of things in Las Vegas, it is lush, well-manicured, and most days features a lot of money changing hands. The wind today, however, is out of control.
Not ideal for a round of golf, but these folks I’m with won’t be deterred. They intend to play, the wind a minor factor in their negotiations over what they’ll be betting on the match.
The group I’m with is made up of professional gamblers, some of them the best in the world, including poker players Jennifer Harman, Eric Wasserman, Mj Gonzales, and Erik Sagstrom. But the man they’ve built the game around—a man who has dueled on the course with everyone from Phil Ivey to Jerry Buss to PGA pros—is a 69-year-old named Richie Sklar.
Richie is older than this crowd, and he’s currently nursing some injuries that make it difficult for him to swing. Still, despite all of their bluster, nobody wants to play him unless he gives them some weight, some kind of advantage. That’s because unlike the rest of them, Richie Sklar is as great a golfer as he is a gambler.
For much of the last 20 years, Richie Sklar has been the most feared golfer in the city of Las Vegas. Not because he’s a scratch golfer or was a plus-three at his peak. There’s plenty of sticks around Vegas. He’s feared because while these other players all made their millions playing poker, Richie made his millions right here on this golf course. Not from sponsorships or tournament prizes or anything like that. Richie Sklar made millions of dollars the same way he’s trying to make money today. By gambling with rich people.
They have trouble agreeing to a game, because Richie—who usually has to give up a lot of weight to the others—is saying he’s injured, and today he’s the one asking for weight. Of course people would naturally be suspicious that Richie is trying to hustle them, so he takes off his shirt to prove it, and shows them the extent of the bruising up and down his ribcage.
The group eventually agrees to a three-team scramble, with Richie on a team by himself, scrambling his own ball (meaning that after every shot the other teams get to choose which of their teammates’ balls to play, while Richie can hit twice and choose the best of his two). That’s a huge advantage for Richie; he told me it’s worth the equivalent of six strokes over nine holes.
But the others are eager to gamble. That is, after all, what they do for a living. What are they going to do, play for fun? And the stakes aren’t particularly high for them, so fuck it. Maybe Richie really is hurt. And anyway, who can really say what will happen out here with all this goddamn wind?
At $2,000 a hole, Richie is playing the other four players by himself, which means he can lose up to $4,000 a hole. But he also can win that much. To him, this is a friendly game. He’s not feeling 100 percent, so he’s fine with the lower stakes. But he’s used to playing for much, much more, in some of the biggest golf money games Las Vegas has ever seen.