I’ve been around gambling since I was 10, when I placed my first wager, $2 to win, on the jet-black Allen Jerkens trainee Devil His Due in the 1993 Iselin Handicap at Monmouth Park. (He finished third; Valley Crossing won the star-studded race that year.) I’ve bet the ponies ever since, added poker in college; have played backgammon and gin rummy for a few decades, and occasionally plunked down on sports. One thing I learned from a young age is to do your own handicapping; besides the enjoyment one finds in studying and learning from a lifetime of mistakes and rarer successes, it is also near-impossible to beat the game regularly. I know very few full-time horse bettors, and in the last few years, met a few full-time sports bettors. In horse racing, here in the U.S., you’re up against your fellow bettor; in sports, it’s even harder because you’re up against the bookmaker.
One of these sports bettors recently told me that there can only be so many winners; while designing and betting off of his MLB model some years ago, he was always fearful that the edges he had found would be discovered by other bettors, and then the betting markets would recalibrate, his advantage lost.
I’ve always been skeptical of tips, sure things, and people who want to sell you their expertise, a.k.a. touts. I’d seen these men on TV or heard them on the radio, citing information I knew was already baked into betting lines. I wondered why mainstream media outlets offered almost no skepticism to their claims. And if they were making good money from betting, I also wondered, why did they want the attention from selling picks for a relatively small amount of money? Who needs the grief?
I knew from experience. For one summer in 2006, I was the official program handicapper at Monmouth Park. Besides picking every race, in the Asbury Park Press’s long-running Daily Double feature I wagered off a mythical starting bankroll of $2,000. I was “The Man” and was pitted against a revolving “Fan of the Day.”
People came up to me all the time at the track to compliment a winning bet or, more likely, a loser. I finished positive by $100 or so, which given The Man’s finishing bankroll in previous years, felt like an incredible triumph. Nobody had to pay for this stuff.
So in the spring of 2015, I started looking at the modern tout industry — bettors who claim that, by paying them, they’ll help you win more than you would without them. I’ve worked on several stories alongside this one, but like any investigative issue, it turned out to be the most exhaustive. You can’t rush the time needed to understand a complex subject.
You can read it here, on Deadspin, a place I had written for before — including a feature on a high-profile horse-racing stable turned Ponzi scheme. I knew their editors had an appetite for a story like this.