I had put a lot of money on the Seahawks to cover a two-touchdown spread. One Sunday evening, we hosted a small Christmas party, where Steve and Ryan asked me how my gambling was going. While my wife and kids ice-skated, I sat in the minivan, our toddler napping in his car seat, as I put together a six-game parlay (lost $80). Point spreads and moneylines ran constantly through my head, mingling with the omnipresent Christmas carols to create a strange backbeat to the holiday season. Months of diligent recordkeeping were abandoned as the flurry of action caused me to lose track completely of how much I had bet, and on what. It was almost midnight—the Christmas tree was glowing nearby, my father-in-law was dozing on the couch, and I had just lost $500.
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Before our first call, I sheepishly sent Silver my week-one bet slips. If anyone could turn me into a respectable bettor, I figured, it was him. He estimates that he has netted in the “mid–six figures” over the course of his gambling life. A few years ago, Silver, citing a midlife crisis and political fatigue, discarded the pundit suits, threw on a baseball cap, and started writing more about gambling.
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- Silver laid out some basic realities of the sports-betting economy.
- This was not exactly what Silver had said, but I could read between the lines.
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Silver laid out some basic realities of the sports-betting economy. He launched a newsletter full of sophisticated sports-betting models and wrote a book about the psychology of successful gamblers. By 2018, Christie’s case had landed before the Supreme Court, which overturned the federal ban on sports betting. Then, in 2012, New Jersey Governor Chris Christie, hoping to boost Atlantic City’s flagging economy, signed a bill expanding sports betting to licensed locations in his state.
One of his clients, he claimed, had made $8 million following his picks; another had made $13 million in four months. “Sometimes people are degenerate,” he conceded. Did he ever worry that his followers might take him literally when he tells them to sell their house for a bet? “I just got limited by the biggest sportsbook in Vegas! Betting in another person’s name violates the terms of most sportsbooks, and depending on how the transaction is executed, it could be considered fraud.
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One of my most valuable resources was a website that aggregated the lines across all sportsbooks and tracked the micro-movements in real time. By October, I had settled into a rhythm with my betting. I had decided in advance not to bet on the game—I didn’t need any action in order to be invested in its outcome, and the stress might sour the family experience. Live-betting odds have been featured on the Golden Globes telecast and CNN’s election coverage.
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Are you staying up late to watch West Coast games with teams whose rosters you know nothing about? Are you going to sleep and waking up thinking about your bets? Bettors who start spending more time or money than usual on the app will receive a notification alerting them to the anomaly—hence the Reality Check alerts I had impatiently dismissed. Carton went to rehab in Arizona, spent a year in prison, and, when he got out, started counseling compulsive bettors and speaking at schools about the dangers of gambling addiction.
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He was suffering the first sports-fan heartbreak of his young life; I was checking on my prop bets. As I toggled between gambling apps, my son sullenly turned off the TV and announced that he was going to bed. I spent some time perusing the Cheesecake Factory–size menu of available Super Bowl bets.
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To avoid detection, some sharps will “prime” their accounts—placing scattershot bets to make themselves look like reckless gambling addicts and prompt the sportsbooks to increase their limits—before moving in for the kill. One reason to doubt the betting prowess of handicappers like Perry, who claims to make tens of millions a year gambling, is that the professional sportsbooks are carefully designed to prevent such success stories. Compared with the solitary swiping of the sports-betting apps, the blackjack table was almost Rockwellian. He led me across the casino floor as I scampered behind him taking notes—the sage professor, goateed and clad in a black oxford shirt, explaining slot machines and table games to his earnest pupil. They seemed to regard sports betting as an insignificant problem—a nice pet issue for Tonko, maybe, but not something worth spending time or political capital on.
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This had become something of a pattern since my experiment began—whenever I started talking about gambling with a couple, the woman would almost invariably tune out or recoil, while her husband leaned in attentively, eager to hear more. The implicated included NBA players and a retired Hall of Fame point guard turned head coach. On October 23, the FBI announced the arrests of more than 30 people in a pair of interlocking gambling schemes.
But professional sports leagues remained determined to keep gambling at a distance. When 17th‑century settlers arrived in North America, they encountered Native tribes placing high‑stakes bets on “little brother of war,” a precursor to lacrosse. Ancient Greeks wagered on the (occasionally rigged) early Olympic Games; Romans bet on chariot races and gladiatorial contests (also sometimes rigged). I knew, of course, that I wouldn’t win every bet. Scale up the wager sizes, multiply across all 272 games in the NFL season, throw in some NBA and college football, and I stood to make—what, $10,000? Like so many wives before her, she had looked upon my foray into sports gambling with a bemused air of exasperation; now she was seeing a potential upside.
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The real offline slots games are here! I knew how they were feeling this morning—the thrill of a win, the sudden appetite for more, the hubristic belief that they just might be savvy enough to make money at this. Staring at that number, I thought about all the people who had placed their first-ever bets on the Super Bowl.
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He was urged on forcefully by parents whose sons had gambled away their tuition money, and by politicians and experts in the United Kingdom and Australia who wished that they’d cracked down on the industry earlier. When he began working on a bill that would ban certain kinds of advertising for sportsbooks, he was surprised by the energy around the issue. Before the game, I showed the parlay to my 10-year-old son, explaining my logic as if I were a physicist explaining a particle accelerator. That night, the Patriots, my favorite team, were playing the Giants on Monday Night Football, and I spent all day putting together what I thought was the perfect play. This was not exactly what Silver had said, but I could read between the lines. Could it be that I was actually good at gambling?
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