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The Wide World of Bookies

Betting on sports is only legal in four states: Delaware, Montana, Nevada, and Oregon. The rest of the country has to make its bets illegally, through bookies. As with any enterprise that holds the promise of easy money, there’s never a shortage of...

All illustrations by Skip Sterling

Betting on sports is only legal in four states: Delaware, Montana, Nevada, and Oregon. The rest of the country has to make its bets illegally, through bookies. As with any enterprise that holds the promise of easy money, there’s never a shortage of hungry gamblers looking to make a few dollars.

A few years ago, when I was working as a bartender in New York, I met a ton of bookies who’d ask me to “hold” envelopes stuffed with tickets and cash for shady customers who’d stop by later to pick them up. I quickly learned that those who operate in this world hail from all walks of life. Some were involved in organized crime, while others were independent operators who only took a few bets for friends and coworkers. Their clients were a varied lot who, for whatever reason, just liked to bet on sports: frat boys, athletes, waste-management guys, firefighters, cops, doctors, lawyers, and former felons. I spent a lot of time with a few bookies and customers in particular, through whom I became familiar with the less savory aspects of the business, starting with how the job actually works.


Illegal bookies base their lines (“money lines”) and spreads (“point spreads”) on calculations made by actuaries for Vegas casinos. These lines and spreads represent a handicapping that expresses which team bookies think is more likely to win. In the days and hours leading up to a game, bookies adjust their lines and spreads to account for the bets (“action”) in their books, fluctuations in the Vegas numbers, and any other unexpected events that could affect the outcome, such as player injuries.

There are many ways to use a bookie, but most customers stick to a few basic kinds of bets. To take this year’s Super Bowl as an example, when the Broncos were the obvious favorite leading into the game, the money line was set at Seattle +110, Denver -130. If you wagered $100 on Seattle and they won, you would get your $100 back, plus an additional $110 (minus the bookie’s “juice,” or commission, usually set at 5–10 percent). If you took the line on Denver instead, a $130 wager would net you only $100, but you would see the return of your $130 (less the bookie’s juice). But you also have to consider the point spread, which was set at 2.5 for this year’s Super Bowl. If you bet on Denver, you would need them to beat Seattle by more than two and a half points for it to count as a win. On the other hand, if you backed Seattle on the spread, you’d need them to lose by fewer than two and a half for your wager to become a winning ticket. Finally, on a “total wager,” gamblers bet on the total points scored by both teams combined. In this year’s Super Bowl, the “over-under” was 47.5, meaning that a wager on the under would pay off if the total points scored by both teams were fewer than 47.5. (This year the over was the winning bet, since the total point score was 51.)


Successful bookies make it their business to learn the habits and tendencies of each of their bettors, basing their observations on an archetypal matrix of sorts: “Sharps,” also known as “wise guys,” tend to do their research, wager larger amounts than most bettors, and generally wait until the last minute to place their bets. They are knowledgeable and unlikely to let sentiment influence their decisions. On the other hand, “degenerates” are often deeply sentimental bettors who place bets they can’t afford, struggle to pay on time, and compulsively wager themselves deeper into the hole. “Schnooks” are unsavvy bettors, more likely than others to get duped, and they rarely come out ahead of their bookies. Schnooks and degenerates are more inclined than other bettors to accept unappealing lines and spreads, and they’re more likely to put in an early wager than to wait for the lines and spreads to settle.

Sentimentality can be a very powerful guide for a gambler’s decision making, and when it comes to the Super Bowl, this sentimentality sometimes goes haywire. This year, New York and New Jersey bookies reported large and unexpected sentimental action on Denver from gamblers hoping to see Manning win another Super Bowl. When the lines first opened, Seattle was the favorite. But within 20 minutes the early action had been pushed out by emotional action, flipping the money line to favor Denver. Nonetheless, bookies reported that unpredictable winter weather could be the deciding factor for the game and for their books, that Seattle would win in cold weather or snow, and that Denver would win if warmer weather prevailed in New Jersey.


As game day approached, and the likelihood of having a snowy Super Bowl increased, the action started to turn back toward Seattle. In the two weeks leading up to the game, the weather was all my bookies wanted to talk about, which was annoying but also made perfect sense. Misjudging the expected outcome of the biggest football game of the year could be a very costly mistake for anyone running a sports book.

Some of the bookies I met came to be involved in the business after running a book for friends, which led to friends of friends and, eventually, a de facto gig. Most were employed, or at least trained, in some sort of legitimate profession; their bookie business was something on the side. A handful had lost their jobs during the financial crisis, with sports books becoming their only source of income.

Dom was the first New Jersey bookie I got to know well, and he lived up to the stereotype—a 6'4" Italian American with prison-yard muscles and a hefty beer gut who could’ve easily walked into Central Casting and stepped out with a bit part in a Scorsese film. He even had the right nickname, “the Two-Ton Gorilla.” He has enormous hands, a square and heavily scarred face, a flattened broken nose, a very loud voice, and a very hot temper. Dom had grown up around bookies and loan sharks, and when he was younger he enjoyed getting into fights. This eventually led Dom to run his own wire room, which he started after a few years in prison for unrelated convictions under the Racketeer Influenced and Corrupt Organizations Act. He employed a team of clerks who handled customers and their bets. Clerking was seen as a very desirable gig. The hours were good, and it was possible for a talented clerk to be put in charge of a wire room or to open a book of his own one day. His right-hand man and unofficial head clerk was an old-timer called Sammy. While Dom set the lines and met with a few customers every week, Sammy and the other clerks would meet with customers daily.


To make a bet, a customer would call one of the clerks, the wire-room number, or Dom’s cell. Most bets came in on game day, because, like the bookies, customers know they can lose money due to unanticipated events, like player injuries. After each game, clerks tallied their books—though they all knew exactly where they stood during every minute of the game—and Dom did the same for the entire wire room. Once the totals were logged for each clerk and customer, they held meetings to exchange money and start setting up the action for the next game.

Sitting in a dive bar in a recently gentrified neighborhood in Brooklyn, I’d wait for Dom, watching as guys would wander in and order drinks, asking the bartender if Dom had been in yet. They’d wait, excitedly talking about how they’d fared in the past week and how they planned to pick winners for upcoming games. Dom would stride in and slam his gigantic hands on their backs. His booming voice would drown out the jukebox as he’d shout to the bartender, “Coors Light and whatever these guys are having! What’s good? How’s the family?” He once introduced me to a pair of customers, a local school-board official and a construction worker, by saying, “This is Rach, my nerd.”

Money would be exchanged, notes would be taken, and the conversation would flow from sports to the weather, politics, women, kids, work, employees, and then inevitably back to sports. Dom’s phone would vibrate incessantly, flashing with calls, texts, and emails. He’d pick up without saying hello, just “Yeah, I’m on my way,” or “Ten minutes, all right, pal?” Calls from anyone he wasn’t due to meet that night were sent straight to voice mail to be handled the next morning.


Then we’d head to his next pickups, where Dom would repeat the same performance with other customers. As night fell, the locations would switch to strip clubs. This was the scene every Thursday night, from about 5 PM to sunrise, as Dom seduced his customers into another week of gambling.

Occasionally he’d binge on cocaine, which would sometimes cause him to freak out, and he often drank heavily. One summer afternoon a few years ago, as we took a leisurely stroll through midtown Manhattan, I asked Dom if he had enjoyed the Memorial Day weekend.

“It was horrible, Rach,” he said. “Had to go to Jersey, Brooklyn, and the Island after work Friday. Then back to Queens before I went home. Got into it with someone I’ve known for years, a good friend. He owed us $30,000. Dumbass shows up at this diner, hands me an envelope, and there’s only ten in it. Ten. Fucking. G’s. What am I supposed to do with that?”
I shrugged.

“I grabbed a fork and stabbed him in his fucking eye, is what I did. You have any idea how difficult it is to poke an eye out?”

I told him I had no idea.

“Neither did I, but it is.”

Before I started hanging out with Dom, I assumed the world of bookmaking would be violent. But it isn’t, on the whole. Physical violence is very rare, and for the most part, the day-to-day is all about proving whose dick has the most swing. Maintaining control over the clerks, making the most money, not letting degenerates and sharps bankrupt the office, and making rivals look impotent are the bulk of the job description. Sometimes, when Dom made mistakes in setting adjusted lines, his unofficial head clerk, Sammy, would take great pleasure in announcing losses the wire room was taking on a game in play: “You see that field goal? That just cost the house $50,000, and it’s only the first quarter!” Despite their occasional quarrels, Sammy and Dom maintained a close friendship for many years until Sammy retired to Mexico. Even now, in retirement, Sammy occasionally returns to New York to help Dom out.


Every year around Super Bowl time, law-enforcement sting operations increase and bookies across the country get busted and thrown into jail, involuntarily forfeiting proceeds of the most lucrative week of their year. Considering that this year’s Super Bowl was held in New Jersey, local bookies were on high alert. Governor Chris Christie has made it clear that he wishes to legalize sports gambling in his state’s casinos, and local bookies were worried that the governor was looking to take down large betting operations to demonstrate the need to regulate a widespread—and very profitable—black market. With this ammunition, the bookies told me, Christie and his cohorts could more easily challenge the leading sports leagues and make steps toward legalizing and regulating sports gambling, in hopes that the collected taxes could rescue the state’s ailing economy.

Both sides in New Jersey’s fight over the legalization and regulation of sports gambling sorely misconstrue the real nature of illegal sports gambling. As anyone who’s spent time with a bookie knows, the wager itself is only part of the appeal. Aside from the amounts won or lost, customers ascribe other values and meanings to these transactions. The juice, or “vigorish,” is little more than a fee charged by bookies for the social experience they provide. The social rituals involved in betting with your local bookie could never be replicated by a state-regulated transaction at a casino or a racetrack, where tickets are processed by bored, nametag-wearing employees sitting behind bulletproof glass in an alcove conveniently located between the bathrooms and the ATMs. What is being proposed in New Jersey would be sterile, impersonal, and joyless: the DMV of the gambling world, which would resemble similarly boring legal gambling facilities in other parts of the country. But of course, the erosion of bookie culture is not a sound legal argument. More importantly, whichever side wins the legal fight, whether it goes to the New Jersey governor or to the sports leagues (which fiercely oppose state involvement in sports gambling), bookies and their customers probably won’t even notice.

This time things worked out for Dom. He didn’t have his most lucrative Super Bowl ever, but considering the difficulty bookies had in calling this game, he was happy to come out on top. The odds on the first score coming from a Seattle safety were +4,000 (or 40/1), meaning that the payout on a $100 bet would be $4,000. As unlikely as this outcome was, those were tempting odds, and some of Dom’s customers made the wager. A few seconds after kickoff, as Denver’s first offensive snap resulted in a Seattle safety and a 2–0 Seahawks lead, the Two-Ton Gorilla sent me a text message: “That killed us.”

But this was the Super Bowl, after all, and in the end Dom was spraying champagne around the bar as if he’d just won a ring of his own. Two days later, having avoided busts and losses, he jetted to Costa Rica, where he runs two online gambling businesses, leaving the wire room in Sammy’s safe hands until Dom returns for March Madness. He makes this trip down south every year, ostensibly to check in with his online sports-book operations at a time in the year when there’s less face-to-face action. Privately, however, he admits that these long trips are more about escaping the NYC winter.

“If I don’t have to be up in the cold, why the fuck would I be?” he said. And the answer is simple: If you’re a bookie who didn’t go bust or get busted during Super Bowl week, you can pretty much do whatever the fuck you want.