In March of 1999 I was an associate editor at ESPN The Magazine working in the football department. It was the off-season, and I needed something to write about, when a senior editor asked me to pick up a story he had planned for our Biz column. One of my colleagues had already begun reporting a piece about the Vegas bookmakers who set the lines for the NCAA basketball tournament. The decisions these bookies make—in an instant the night the 64-team field is selected—directly impact the billions of dollars that are bet. But the original writer was pulled off the story for another assignment, and he handed his contacts over to me.
The first name on the list was Joe Lupo, the head bookmaker at the Stardust in Las Vegas. The Stardust was the inspiration for the sports book in the movie Casino, and it’s always been the first sports book on The Strip to set the lines. Lupo was a great interview—open, a colorful storyteller and patient when explaining his world. After the piece ran, I asked him if he’d be interested in expanding the story into a book, over an entire season. He was into it. Then I asked him if he thought any professional bettors, wiseguys in Vegas parlance, would be willing to be as open with motivations and dollar figures as he was. He laughed at me, but promised he’d ask around.
For two months I heard nothing. And I assumed that Lupo was right: no wiseguy was going to tell me what he was betting on, why he was betting, and how much it was costing him. Then, in late May, while walking through the airport in San Diego, I got a call from Alan Boston. His voicemail was an electric rant that ranged from his old coke habit to the five figures he had riding on Andre Agassi in a tennis tournament that day. By the time we finally spoke several days later, Boston, an Ivy League grad and a voracious reader, had decided he was in. Lucky for me.