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The Beats Go On

Think legalization and mobile betting are going to wipe out the old-school bet taker? As one anonymous bookie writes: Think again.
As told to Ben Pickman

What’s changed in the three years since the Supreme Court granted all 50 states the right to legalize sports betting? Everything. By the end of 2021, online or in-person wagering will be sanctioned in more than half the country. Revenue is skyrocketing. Leagues are evangelizing. And booming business means big changes for anyone who operates, plays, covers—or bets on—the games we love. Welcome to the Gambling Issue.

As I watched confetti rain down onto the University of Phoenix Stadium field after the Giants’ historic upset of the unbeaten Patriots in Super Bowl XLII, I felt scared. Very scared. I was in Miami, watching the game on TV alongside my brother. To that point, I had built up a pretty good business. Most of my guys were young, people who didn’t really have access to a ton of money. So at the time, I wasn’t really taking any large bets. Still, a lot of futures had been placed on the Giants, who were 12-point underdogs. When they won, my bankroll of around $25,000 was basically wiped out.

As a sports bookie, you never want to be known as a guy who can’t pay out. That would ruin me forever. I was supposed to leave Miami on the Tuesday following the game, but after the Super Bowl I rushed back to my hotel and booked a flight to arrive home that night, so I could start figuring things out. In that moment, I questioned why I was doing this. I thought it was over. But I took some advances and got everybody paid out—I even started a fantasy league that summer and collected up front so I could have the cash for my bankroll. It was risky, but it’s in my blood.

Losses like that sting, but most Sundays aren’t nearly as dramatic. I usually arrive at a local bar at around 1 p.m., figure out what screens I want to watch and check the iPhone app I use to track my action. I’m looking to see where my liabilities are. For a given 1 p.m. ET slate, I have around $60,000 to $80,000 pending, with another $30,000 to $40,000 on the 4 p.m. games. Then, I’m just like any other guy who’s screaming at the TVs, hoping for the outcomes I need.

I’ve been on my own for around two decades. And my business has recovered from that day in 2008 when Eli Manning and David Tyree connected. Since I started, sports betting has become legalized where I live, as it has in nearly 30 other states. I have a couple of friends who are also in the business, and we were all pretty nervous when the markets opened up. But the thing with illegal bookies is, some bettors like working with people they can build a relationship with—not to mention a more flexible payment plan. I’ve lost a few guys who would bet only on the occasional fight or golf tournament, or only on the Super Bowl. The number of prop bets that legal sportsbooks offer also leads money to sometimes go elsewhere. But in truth, I really haven’t seen that much of a difference in how much action I get.


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Even before sports betting was legalized, I never thought what I was doing was that bad. I knew some older guys who had been arrested or slapped on the wrist, but nothing really ever happened to them. I wasn’t in the mob. I wasn’t violent. I wasn’t extorting anyone. People were going to bet somewhere, so why not do it through me? Still, I now feel some vindication, a reinforced sense that I wasn’t doing anything wrong.

I first got into gambling in high school. My friends and I—all sports fans—wouldn’t do anything big, $25 bets here or there. It seemed like we would always lose. We’d call our old-school bookie on his landline and leave a message about what teams we wanted to ride or tell him when we would be bringing our money over. Eventually, I was like, Screw this. Let me start taking the action. I wanted to be on the winning side.

Over the years, I’ve won a lot more than I’ve lost. I can win 25 weeks in a row, but when I lose three or four weeks consecutively, I still catch myself complaining. I work a full-time day job, but there’s a thrill involved with sports betting that keeps me going. On Sundays, when I log on and see the money pending, it makes me feel alive.

Oh, and Tom Brady. He’s become my favorite NFL player. Sure, he’s cost me tons of money—the Patriots’ 28–3 Super Bowl comeback over the Falcons cost me what would have been the most I’d have ever won on a single game—but the more people hate him, the more I love him. Like me, he’s been vindicated.

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