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Requiem for a Sports Bettor

Gambling on sports has never been more high-stakes or more accessible. But with the invasion of Europe-based companies in the game, the pros are feeling squeezed and routinely getting banned from plying their trade. Is this the end of the professional sports bettor?

John W. Tomac

“I am not a bookmaker,” Gadoon Kyrollos tells me as we walk through the Hard Rock Casino in Atlantic City, playing penny slot machines. “I’m a sports bettor.” Kyrollos is actually one of the highest-rolling sports bettors in the United States. He bets millions of dollars each year on sporting events, from NFL games to the Nathan’s Hot Dog Eating Contest. He’s known throughout the gambling world by the name Spanky, and in his hoodie, sweatpants, and backpack, he very much resembles a 40-year-old version of the Little Rascal. His backpack, however, isn’t carrying school books and snacks. It’s filled with bricks of cash, nearly $150,000 worth.

“Bookmakers hang a number,” he explains, as he pantomimes holding a gun sight up to his eye and pulling the trigger. “And I snipe ’em.”

Despite the bag full of money, Spanky is transfixed by the penny slot machine, pumping one bill after the next into it. On his cellphone he consults a spreadsheet that tells him how to play this particular machine so that it is “plus EV,” or positive expected value, meaning the player has an edge over the machine over time. “This is some real insider shit I’m showing you right here,” he tells me, referring to his spreadsheet, which has formulas for dozens of different slot machines plugged into it. “I mean, it’s probably an edge of, like, $12, but if you were walking down the street and saw $12, you’d bend down and pick it up, right?”

It’s important to Spanky that I understand the difference between bookmaking and betting, because a lot of people don’t understand or appreciate the distinction, including the Queens district attorney, who charged Spanky with bookmaking in 2012, a charge he says stemmed from a widespread misunderstanding of this business.

That misunderstanding stands to spread like wildfire. Last year, the Supreme Court repealed the Professional and Amateur Sports Protection Act of 1992, paving the way for individual states to lift restrictions and regulate bookmaking. New Jersey, where Spanky has lived his entire life, was one of the first states to do so, and in less than a year it has experienced a gold rush. There are now 10 physical and 14 online sportsbooks in New Jersey that have collectively already handled more than $1.5 billion in wagers. Seven other states have moved quickly to follow New Jersey’s lead, with 29 more currently considering sports-wagering bills in their state legislatures. But the way the business is taking shape in the United States troubles many professional gamblers, including Spanky, who has invited me to Atlantic City so I can learn more about what he calls the “dying art form” of bookmaking. He and I will pool our money, with me putting up 1 percent of the stake, and he will show me how to bet like a pro. Then I can see firsthand how the corporations that are taking over the sports betting industry in the United States have killed off the art of bookmaking, and how they’re killing off the professional sports bettor in the process.

As we walk down the Atlantic City boardwalk on a cold Monday night in March, the 40-year-old Spanky quizzes me on my knowledge of sports betting. “If I said you should bet the over at 134.5 and you see the number is 135, do you bet it?” “No,” I respond, not entirely sure whether I got it right, but careful to not show any hesitation. “That’s right. What if I said you should bet the Lakers +7 and the number is 7.5, do you bet it?” “Yes,” I answer, this time more confident I was right.

“See, you know what you’re doing. But you’d be surprised how many people have trouble with that.” I don’t tell him that I wouldn’t be surprised at all. We stop at the edge of the Ocean Casino at the end of the boardwalk. Spanky hands me the backpack. “I gotta leave you here. You don’t want to be seen on camera with me.” Why not?, I ask him, trying to mask my concern. “They don’t let me bet in there. And if they saw you talking to me, they probably wouldn’t let you bet, either.”

According to the industry research firm Eilers & Krejcik Gaming, sports gamblers fall into seven different categories: casual dabblers, status seekers, super fans, action chasers, would-be pros, high rollers, and sharps. These personae exist on a spectrum, where some of them develop into others as they climb the ladder from casual dabblers to the vaunted sharps—the players who can beat the house edge on a regular basis. Spanky has at one time or another been all seven. Today he’s known as a sharp player by every major bookmaker in the world. Which means his bets are often limited. For some bookmakers it means his action isn’t welcome at all.

Spanky shakes my hand and turns and walks off down the boardwalk. I take a deep breath, sling the backpack, heavy with cash, over my shoulder, and head into the casino.

In the less than one year that bookmaking has been legal in New Jersey, a number of European companies have swooped in to offer their services to the racetracks and casinos licensed to book sports bets. These companies offer a turnkey operation complete with quantitative analysts, technology for things like mobile wagering, software and modeling for profiling bettors and managing risk, access to data from sports leagues, and worldwide pools of liquidity. For a casino or racetrack unsure of how to run a sportsbook, or wary of getting involved in the highest-risk offering in the gaming business, these companies are making offers that can’t be refused. “To borrow a cliché, the U.S. is viewed as the land of opportunity within the industry,” says Paris Smith, CEO of Curaçao-based Pinnacle, one of the largest sportsbooks in the world. “It is also seen as a prize to be won for European operators and suppliers that have had to endure the maturation and saturation of its markets in recent years.”

But for gamblers, especially the professionals, the rapid expansion of some of these European companies in the American market is alarming. The European model of bookmaking is seen by many as hostile to winning players. During a panel at this year’s MIT Sloan Sports Analytics conference, entitled “Skin in the Game: Sports Gambling’s Emergence in the U.S.,” moderator Jeff Ma challenged one of the panelists, Sharon Otterman from the U.K.-based bookmaker William Hill, over its perceived practice of aggressively limiting and banning winning players. Otterman defended her company by saying, “We have a business. We’re not a not-for-profit.”

Professional sports bettor Alan Denkenson thinks the explanation is much simpler than that. “It’s easier to book your money with squares,” he tells me. He is still allowed to bet with William Hill, though “right now I’m one of their sharper bettors because they’ve thrown everyone out. One day when they throw me out someone will take my place. … When you make a few big bets you’re allowed to lose. If you grind it out to get to $20K you’re going to get thrown out.”

It isn’t just William Hill, either. DraftKings, the daily fantasy sports company that has pivoted into bookmaking in New Jersey, has signed a deal with Kambi Group, which is headquartered in Malta and takes a similar approach to so-called sharp players. And players don’t have to win $20,000 to attract attention, either. “I was just following baseball games and making bets on ‘runs scored in the next inning: yes or no,’” says “Captain” Jack Andrews (not his real name), a professional gambler who lives in New Jersey and comments pseudonymously on gambling forums and Twitter. “By mid-September I was down $600 betting at DraftKings and I noticed I could not bet more than $100 on any of those inning bets.” Andrews then saw his bets on every sport were limited, including the NFL. “Nobody should be afraid to take any bets on the NFL because it is highly efficient. The number has been hammered into shape by the time the weekend rolls around.” To prove it, Andrews tries to make a baseball bet on his phone. He is limited to a maximum bet of $30.26. “Thirty dollars? Really? DraftKings has bragged about how many different bets they’re taking, a half a million a day, and my $50 is really too much for them?” (DraftKings declined to comment for this story.)

Not being able to bet more money is a death sentence for professional gamblers. “I work on very small margins and so does any pro sports bettor,” says Bill Krackomberger, the creator of the gambling app KrackWins and star of the Showtime docu-series Action. “For every 100 that goes over the counter, we’re very happy with 102 or 101 coming back. I know it sounds crazy. I have to be able to bet five and six figures on a weekend in order for it to be worth a living to me.”

The situation, then, is existential. If this is the direction the industry is headed, professional sports bettors may soon be no more. There will only be bookmakers and squares. And once the bookmakers are done feasting on the squares, there will be nothing.

“It just seems so un-American for a company to say, ‘Come on, take your shot at us, we’re here for the gamble,’ and then when you do they say, ‘No, you’re too smart, we only want to take the action of people who don’t know what they’re doing,’” says Captain Jack. “It’s predatory. They’re being encouraged to walk into a buzz saw.”

The William Hill Sportsbook at Tropicana Atlantic City
Getty Images for William Hill US

In 1993, the Mt. Carmel Feast in Jersey City had all the elements of a modern carnival: rides, corn dogs, skill games where you could toss rings or pop balloons to win stuffed animals. But down an alleyway, behind the church, there was another game—one that wasn’t open to the general public. Groups of young men crowded around a table taking turns rolling dice, playing an old carnival game called “over/under,” where players bet on whether each roll would be over or under a seven.

Spanky Kyrollos was 15 years old when he first discovered the illicit dice game at the fair. He was instantly captivated. He grew up in a family that loved to gamble. He learned math by adding up playing cards. He learned poker at family gatherings. And whether his siblings and parents and cousins played backgammon or chess or cribbage, money was always on the line.

By the time he was a teenager, Spanky knew he had a knack for numbers. He saw math as a form of problem solving, like discovering secrets. As he watched people bet on over/under he figured the odds in his head. The game was paying off even money for over and under seven, and 4-to-1 when the dice rolled seven exactly. He knew the odds were off, and it was a bad bet to play. But it got him thinking—the folks on the other side of that table, the ones taking bets from the players, they were going to make a killing.

That same year, a friend of his at St. Peter’s Prep came to school selling parlay cards—in which you could pick a number of football games and win big money if they all hit. Cards cost $5 each, and every week it seemed like somebody would hit one for $100, which kept everyone wanting more. Spanky looked at it like the dice game. He realized the odds were skewed so you weren’t winning as much as you should given how difficult it was to hit. He also noticed far more kids bought cards than were winning each week, and even after paying off the occasional lucky winner there was still a lot of money left. He didn’t buy any parlay cards. He asked the boy who was selling them how he could get cut in.

Spanky soon started selling parlay cards for the local bookie to his barber, to the kids in his neighborhood, to family friends. He was getting a cut of the losses, around $100 or $200 a week. It was huge money for a high school kid in the 1990s. He brought his parlay card business with him to Rutgers, and his earn more than doubled. But he blew most of the money betting on sports, “complete sucker shit.” He had always prided himself on being able to solve puzzles and figure out how to beat the odds. But sports betting was proving a tough nut to crack. “Whatever I made on parlay cards I gave most of it back to the bookmakers,” he says. “I was a degenerate.”

In 1917, as the United States entered World War I, a number of countries in Europe suspended horse racing, and various U.S. states were considering banning it for reasons both patriotic and moral. The U.S. government had issued a war tax on racetracks, and some smaller tracks shuttered as a result. The nation’s bookmakers soon took up residence in the grandstands of America’s baseball games, barking out bets on every pitch, and often taking in more money than the ballpark did on admission. By 1919, gamblers had so permeated the world of professional baseball, the World Series was fixed by a syndicate of big-money gamblers in what would become known as the Chicago Black Sox scandal.

Soon American gamblers spread their wings to college football, and throughout the Great Depression gambling on sports only increased, with more than $60 million a year wagered in New York City alone. A story in The Saturday Evening Post in 1936 called it “America’s fastest growing industry,” noting that the new breed of sports gamblers were “Wall Street types,” and “adept at figuring percentages, odds, and statistical permutations.”

One such Wall Street type was a securities analyst in Chicago named Charles McNeil. He started gambling in the bleachers of Wrigley Field, and soon found himself making more money from gambling on baseball and football than he made at his day job. He quit and turned to gambling full time. Once bookies figured out how sharp he was they stopped taking bets from him, so by the early 1940s McNeil went to the other side of the desk and started making book himself. He had an idea he thought could actually level the playing field between bookmaker and handicappers like him, and he believed it would prove popular among gamblers and bookies alike. His innovation, which we today know as the “point spread,” would revolutionize the gambling world.

McNeil set a “line” for every contest he took wagers on, giving the team he believed to be the favorite a certain number of extra points they would need to win a game by for a bet to pay off. In doing so, he turned every contest into something closer to a coin flip. By offering bettors a fair contest, he would ideally attract equal action on both sides. By offering to pay $10 on an $11 bet, he would keep $1 from all of the losing wagers.

Point spreads proved popular, and soon a publisher in Minneapolis named Leo Hirschfield began publishing the spread for games all over the country. He employed a team of handicappers who talked to contacts across America to obtain information to set their lines. Hirschfield then provided these lines to America’s bookies for a fee. The service, known colloquially as the “Minneapolis Line,” helped bookmakers minimize their risk, which enabled them in turn to raise their betting limits.

By 1949, there were 23,000 miles of telegraph lines leased from Western Union to service 20,000 bookies with up-to-the-minute sports data. Those bookies in turn provided that information to other smaller bookies. In all there were estimated to be more than 270,000 bookmakers earning their living from sports betting in the United States in 1950. By 1960, there were more than 300,000. As attorney general, Robert Kennedy made shutting down the illegal sports betting network in the United States a top priority, believing the proceeds were funding organized crime. Despite his efforts, by 1972 the number of people working in the illegal bookmaking industry in America eclipsed a million.

Spanky graduated with a degree in computer science and went to work at Deutsche Bank right out of college. He was earning decent money but he was still spending a lot of time betting on sports. He read books on handicapping and betting systems. He looked for patterns, for edges wherever he could find them. In the 1990s, sports betting was moving to the internet, with black market bookies decamping for the Caribbean to operate their bookmaking business far from the arm of U.S. law enforcement. As Spanky combed through one sports betting website after another, it dawned on him that he could use his computer coding skills to beat the bookies. He could do the same types of things he was doing for finance banks to give himself an edge on sports bets. While sitting in a pizzeria watching a basketball game with his then-girlfriend, he told her his idea. Her response was a shrug. “Yeah, whatever,” she said. She knew her boyfriend loved puzzles and games. She had no idea how much this particular puzzle would consume him.

Spanky approached a coworker he respected and shared his idea for writing code that could identify positive expected value in sports betting markets. The two of them wrote a code that scanned the 80-plus online sportsbooks’ various lines to look for “middles,” or opportunities to arbitrage lines that were different at various sportsbooks. For example, if their program found a line on a football game at one sportsbook, say the Steelers +4.5, and found a different line on the same game at another sportsbook, say the Steelers +2.5, they would make a bet on the Steelers with one sportsbook and make a bet against the Steelers at the other. Most of the time they would win one bet and lose the other, and only lose the “vig,” or the percentage built into the bet as a commission for the bookmaker, usually about 10 percent. But whenever those games fell right in the middle of the two lines, in this case if the Steelers lost by three points, then they would win both of their bets.

They put their program to work, and during their lunch breaks at Deutsche Bank they would walk to the Western Union office to wire money to sportsbooks to bet, using their sign-on bonuses from their jobs as a bankroll and betting about $2,000 a game. Bet after bet Spanky and his colleague just kept losing the vig, never hitting the middle. When they finally hit one for $4,000, Spanky says they jumped and danced around the office. Then they hit another, and another, and another. They kept this up for two years without ever taking a dime out of their online accounts. The first time they requested a withdrawal, Spanky says, the bookmaker had them meet someone on the street in Manhattan rather than cash the money out directly to their bank. A total stranger handed them a sack full of cash. They rushed back to Deutsche Bank and counted it in the restroom. There was $40,000. They had never seen that much cash in their lives. It wasn’t just numbers on a screen anymore. It was real money. How big, they wondered, could they make this? The bank they worked for did the same thing they were doing but in financial markets, and their bosses were all filthy rich. Could betting on sports make them rich, too?

Atlantic City

The Ocean is one of Atlantic City’s newest properties, and the tallest on the boardwalk. Built in 2012 as the Revel, the casino closed after less than three years and stood vacant for four years, a towering monument of Atlantic City’s declining fortunes. In June 2018, the casino reopened as Ocean Resort Casino. Though the property is one of the glitziest in Atlantic City, it is one of its lowest-earning casinos. And on a Monday night in March, it shows. There isn’t much of a crowd as I amble into the 7,500-square-foot luxury sportsbook with my bag full of money.

I ask to speak to the manager, and let him know that I’m going to bet the NCAA and NIT tournaments, and that I plan to bet big. “What are your bet limits?” I ask.

“Oh, there’s no limit,” he laughs.

Fearing he mistakes me for the piss-poor square I clearly look like, I ask, “So I can bet $10,000 a game?”

“Sure,” he says. “You’ll just need to fill out some IRS forms and get a player’s card.” I fill out all the necessary paperwork, then ask to bet $10,000 on an upcoming NIT game. The teller takes my money and punches the bet into a computer. He waits a few moments, then looks up from the screen and says, “They’ll only let you bet $5,000 on this game.”

Who is they? I ask.

“Vegas.”

Back in the 1960s, Bob Martin knew the guy who ran the cleaning crews at the Las Vegas airport. Every day he’d swing by and pay them for copies of whatever newspapers they had gathered up on the incoming flights. Those newspapers, from towns large and small, far and wide, were his bread and butter. He’d scour their sports pages looking for information on athletes, injuries, weather conditions, anything that wasn’t widely known. He’d use that information to make bets at the various “turf clubs” around Las Vegas.

In those days, though sports betting was legal in Nevada, the casinos didn’t operate their own sportsbooks. The 10 percent tax on bets handled was too high to make a profit, since sportsbooks were expected to earn roughly only 4 percent over the long run. So sports bettors had to get down their bets at a number of independent, free-standing “turf clubs” around the city, which eked out a profit by playing fast and loose with the IRS and by trying to win more bets than they lost. This meant the early bookmakers in Las Vegas were mostly no different from the gamblers who bet with them. The books couldn’t rely on simply balancing both sides of a game and earning the vig. They had to take positions, to be invested on one side of certain bets. Essentially they had to gamble against their customers.

“We were gambling all the time,” says Vic Salerno, the founder of Leroy’s Horse & Sports Palace and an inductee in UNLV’s Gaming Hall of Fame. “I remember having Sugar Ray Leonard versus Hagler. And looking at the prop, I would have probably had to close the place if Hagler won.”

“There’s 12, 14 games on a Sunday—what we really want to do, we really don’t want to be balanced on each game,” Salerno says. “If we win three games we will probably break even. If we win four, we’re making money. If we win five, we’re going to make a tremendous amount of money.”

When Martin arrived in Las Vegas in 1963, the bookmakers didn’t make a tremendous amount of money. Hirschfield and the Minneapolis operation had closed up shop in 1961 after Robert Kennedy convinced Congress to pass a number of new antigambling laws. That meant that among legal bookmakers operating in Las Vegas, there was no agreed-upon line for games. Each bookmaker was on their own to take a position. And lines up and down Glitter Gulch sometimes differed wildly. When Martin made his way through town making bets, those lines would quickly coalesce around whatever he was betting, because his opinion was often more respected by the bookmakers than their own. In 1967, Harry Gordon at the Churchill Downs Race and Sports Book had had enough. He asked Martin to come work for him to manage the book and make his lines. Martin agreed, and soon Churchill Downs was considered the “originator.” Once Bob Martin hung up a number, people flocked to payphones to call bookies all over Las Vegas, and likely all over the United States, to tell them what it was. This became known around the country as the “Las Vegas line.” By the 1980s, the state dropped the taxes on the pool of money handled by sportsbooks and the major properties like the Stardust and the Hilton cashed in with luxurious sportsbooks that featured seas of television screens and lit-up electronic boards flashing constantly updating odds and lines. Las Vegas remained the epicenter of the sports betting world, both legal and illegal, for nearly a half-century, until the internet changed the landscape in ways Bob Martin and his stack of small-town newspapers could never have imagined.

Early on a Tuesday morning, I arrive at the Ocean sportsbook and sit in the front row of seats, my bag full of money clutched in my hands at all times. Whenever Spanky has a pick for me, he’ll send me a text. My second bet of the day is limited to $1,000. The teller can’t believe it. “I’ve never seen that before,” he remarks after reading the message on the screen from William Hill’s trading office in Las Vegas. “I’ve taken bigger bets than this before.”

“Like how big?” I ask.

“Ten, twenty thousand.”

“What’s the biggest bet you’ve ever taken?” I ask.

“A hundred thousand dollars.”

“No shit,” I say, truly incredulous. “And all I can get is $1,000?”

“They must be really scared of you, man. Have you been winning a lot of money?”

“I haven’t cashed a single ticket,” I say. “Yet.”

DraftKings Opens “DraftKings Sportsbook At Resorts”
The DraftKings Sportsbook at Resorts in Atlantic City
Photo by Bill McCay/Getty Images for Draft Kings

After three years of betting on sports on his lunch breaks and on weekends, Spanky Kyrollos was earning more from gambling than from his finance job. He told his wife that he and his partner were quitting Deutsche to pursue their sports betting business full time. Years ago in the pizza parlor after Spanky told her his idea to write code to help him bet on sports, she had dismissed it as a flight of fancy. This time she knew he was serious. “Are you crazy?” she asked. His wife’s mother and his mother teamed up to try to talk him out of it. “People would kill to be 24 years old making six figures,” his mother told him. “I can’t look someone in the eye and tell them my son is a professional gambler.”

Spanky didn’t listen. “Nobody knew my business better than me,” he says. “I’m a gambler. It’s a gamble. It’s a life gamble that I took.” He had been betting on sports for years on the side, and had proved to himself that he could be profitable. Not only that, if he had more time to devote to it and more help with it, he believed he could scale it up.

He and his partner quit their jobs and hired a couple of old friends as their first employees. To place as much money into action as they needed, they had to make bets in literally hundreds of accounts in sportsbooks all over the world. They wrote code and built betting robots that could automate the bets for them. They taught their friends about how their system worked, and got the friends to a point where they could work virtually independently.

Much of their business was being done with online offshore sportsbooks, most of which were located in Costa Rica. Many of the proprietors of the websites headquartered there were people who had learned the business as illegal bookmakers in the United States. Spanky flew down and worked out deals with the bookmakers to give him credit, rather than requiring him to post large sums of money and cash out through e-wallets like Neteller every time he won. If he could bet on credit, they could settle up stateside in cash. After all, placing sports bets in the United States wasn’t illegal, only bookmaking was. And bookmaking in Costa Rica was legal. So nobody was doing anything wrong, they figured.

One day, while Spanky awaited the birth of his daughter in the hospital, his partner went to a Dunkin Donuts to pick up some money an offshore book owed them. The partner and the offshore book’s contact exchanged the money in the parking lot. Then, as they got in their cars to leave, they were surrounded by police officers with their guns drawn. Spanky’s partner was pulled from his car and it was searched. “Where’s the trap door?” they shouted. Trap door? For what? “For the drugs!” “This isn’t for drugs,” Spanky’s partner exclaimed. “It’s for gambling!”

Though the police let him go without pressing charges, Spanky’s partner quit the business. The other employees, shaken, followed him out the door. The only person who stayed on with Spanky was one of his former partner’s old friends, a poker player named Michael Duong whom everyone affectionately called “Chinese Mike.” Mike brought Spanky a few guys he played poker with to interview for jobs. “One guy showed up for the interview in a T-shirt with the periodic table on it and I said, ‘You’re in,’ automatically.” They also hired some students from Princeton University who were skilled at coding. He even expanded his operation beyond middling games, and together with his new brain trust developed new models that allowed him to take positions on games. “I realized there were two ways to make money in this business: fundamental analysis and technical analysis. Fundamental analysis is handicapping. You make numbers. Technical analysis, you look at the market. You anticipate where the market is going and get ahead of it,” he explains.

His team started spending their days watching screens with lines from sportsbooks all over the world, and using finely tuned models to analyze the various line movements and interpret what they meant. In some ways it was similar to what day traders might do in the stock market. Sports gamblers call these types of players “steam bettors.” Bookmakers call them “board cleaners.” Both groups tend to revile them. “People say you’re not a handicapper, you’re a bottom feeder, a leech,” Spanky says. Perhaps the contempt was because “chasing steam” was effective. By 2010, middling and steam betting had made Spanky what he deemed a fortune, and he had made a name for himself. “If you were betting sports professionally you knew who I was because I had a big footprint and I moved the line,” he says.

After Congress passed the Unlawful Internet Gambling Enforcement Act in 2006, it became next to impossible for American gamblers to deposit and withdraw money from offshore gambling sites. Many bookmakers repatriated to the United States, figuring they’d do better operating in cash and taking their chances with local law enforcement. Not all bookmakers decamped from the Caribbean, however. Those who stayed behind had to largely forgo doing business with the American market. BetCRIS and Pinnacle paid top dollar to retain the best oddsmakers, and the two offshore sportsbooks soon supplanted Las Vegas as the worldwide “originators” of the betting lines.

The rest of the world’s sportsbooks, meanwhile, had grown stale. Johnny Aitken, who went from working as a runner for a major gambling syndicate in Australia all the way up to becoming CEO of the Australia-based sportsbook PointsBet, watched it happen. “I observed from afar some of the European management models,” he says, “with clients being banned or even limited on the Super Bowl for $20 when they’re trying to bet $20,000 on the favorite.” The European model looked a lot like the earliest days of sports betting in the United States, when bookies offered absurdly skewed odds and refused to take bets from anyone who showed an ability to win. This model depended on large numbers of “recreational” gamblers to work, since with such restrictions it would be hard to attract gamblers who were willing to bet large sums. But recreational gamblers either get lucky and win or they go broke, and if they get too lucky, too often they get banned. Either way there is a law of diminishing returns for the bookmaker who will tolerate no risk, unless that bookmaker can continually locate new, untapped pools of players, like an energy company constantly looking for new pockets of oil or gas buried beneath the shale.

These became the two prevailing models of bookmaking. On one side were the European-style books. On the other side were companies like Pinnacle, who offered lower odds and took on larger bets. Pinnacle and BetCRIS were known to let certain sharp players bet their lines before they went public. “It sounds somewhat counterintuitive,” says Pinnacle CEO Paris Smith, “but sharp customers are actually providing valuable information that feeds back into our pricing model to tighten our odds.” Their traders then adjust their lines based on how those gamblers bet before they offer them to the world. This helps Pinnacle make sure they’re on the “sharp side” of the action, so when the best gamblers win, ideally Pinnacle does, too.

It’s a model that means Pinnacle operates on lower margins, but that hasn’t hampered the company. Pinnacle CEO Paris Smith declined to disclose how much money the company handles, but the rumors are that it’s substantial. “If we were ever to get the real numbers from those offshore places our mouths would drop open,” says Captain Jack. “I’ve heard that $1 billion a month is not that unusual. Nevada does $5 billion a year.”

Back in the United States, the sportsbooks in Nevada were trying to manage their risk from sharp players while still honoring the idea that if you offer a bet, you should be willing to accept action, no matter who it’s from. There were limits, but they weren’t the same for everybody. “They’d have posted limits for everyone. A high roller, casino player, someone they know well they might take more from,” says Rufus Peabody, a professional sports bettor and cohost with Jeff Ma of the Bet the Process podcast. “Someone like me could go in and bet house limits that are posted on the wall. … That’s how its always been. If you can beat us, good for you, but you’ll only get house limits and we will move on your action because there is signal in what you’re betting.” What Peabody means is that sportsbooks could use the information that came from learning what sharp players were betting, so by limiting their exposure they could create a win-win situation for themselves and sharps. One side gets a bet at house limits, the other side gets valuable information. This is the way it worked for many years, more or less. But according to Peabody, the days of posted limits and sharp players being able to bet started to end when William Hill arrived in Nevada.

“I don’t consider the U.K. people bookmakers, they’re more like an insurance company,” says Vic Salerno, who grew his single strip-mall sportsbook into Nevada’s first sportsbook chain, with 72 locations and kiosks throughout the state. Salerno then sold Leroy’s to William Hill in 2012. Since the acquisition of Leroy’s, William Hill has expanded its market share in the state. Of the 190 physical sportsbooks in Nevada, William Hill operates more than 100. And the company’s presence in Nevada was quickly felt by the state’s professional gamblers, many of whom complained that William Hill began aggressively banning or limiting players who consistently won money. “We never really had this thing of kicking people out,” says Salerno. British companies “have the attitude that if someone is consistently winning, why do you keep taking their bets? And that’s completely different.”

“The vast majority of serious sports bettors are banned from William Hill,” says Peabody, who hasn’t been allowed to bet with the company in Nevada since 2017. “If you beat the line you get banned.”

“William Hill throws people out quicker than a 100 mph fastball over home plate,” says Bill Krackomberger. “The European way of cutting people off is really dumb. If someone is good enough to beat you why not use that information internally? Take the bet at a smaller amount and use it to move your line.”

When asked for comment, William Hill sent the following statement through a PR firm:

It is completely false to say that we ban people simply for winning. There are literally tens of thousands of customers in Nevada that are winners at William Hill. That’s one of the great things about sports betting—a lot of customers do win.

In the rare situation where we do prohibit someone from wagering with us, there are a variety of reasons why. They include the sharing of accounts (usually tied to someone who previously has been banned), betting on behalf of third parties, screen scraping and other efforts to “game” the system, as well as compliance reasons or being offensive to staff and/or other customers.

If someone tells you that the reason that they are prohibited from wagering with William Hill is because they are winning, they are not telling you the whole story.

“That seems very dishonest,” says Peabody. “I wish they’d be more honest about it. That’s what grinds my gears is when they say they don’t do it when there’s so much evidence to the contrary.”

Krackomberger was less diplomatic about William Hill’s statement. “That’s total bullshit. Total, total, utter bullshit and you can quote me on that.” Krackomberger is also banned from betting at William Hill in Nevada, and when he visited Monmouth Park in New Jersey to film for the Showtime show Action, his producer was told by management that Krackomberger wasn’t allowed to make any bets there, either. Krackomberger says he’s never done any of the things the William Hill statement listed as reasons for banning players. “They can say all the stuff they want to make themselves sound good, but us guys that are the true professionals, we can tell you the truth,” Krackomberger says. “You should feel like a sucker that you’re allowed to bet at William Hill while Krack and Spanky and these other guys aren’t allowed to.”

By 2010, Spanky says he was allowed to bet directly in only five places in the entire world. He had three kids, with a fourth on the way. His business had been profitable and predictable. His employees were happy. He was becoming a wealthy man. But the European-style changes in the market could potentially kill his livelihood. His “theoretical hold,” meaning the amount of money he should expect to earn from every dollar he bets over the long run, was between 1 percent and 2 percent, the absolute thinnest of margins. That meant that he needed to keep millions of dollars in action to earn enough to support his family and his employees. And with so many sportsbooks refusing his action, he needed to get creative.

“Most bookmakers are failed bettors,” Spanky says. “It’s an ego thing. And because of that they’re betting with other bookmakers.” Spanky reached out to bookmakers who would no longer accept his bets, and he offered them a new deal: They could become his partners. They would provide Spanky with their own accounts to bet into with other bookmakers, and they could split the proceeds. These bookmakers already knew he was a winning player, and most leaped at the opportunity to make a profit off his plays, while at the same time taking a bite out of their competition.

Lining up partners became Spanky’s full-time job, since so many of them would get shut down within a few days for being too sharp. Bookmakers were more skittish about taking on risk than Spanky had ever seen before. That cautiousness, he thought, could have been a function of so many bookmakers just copying other bookmakers’ lines as their own. With so little independent data and analysis of their own lines, bookmakers were flinching at every shadow.

Around noon, Spanky texts me and tells me to try to get $10,000 on Xavier -5 against Toledo in the first round of the NIT. The line for the game isn’t yet on the big screen in the sportsbook, so I ask the manager, and he picks up the phone and calls Las Vegas. He comes back and tells me I have a bet at $5,000. I give him the money and take the betslip, then return to my chair in the front row. The game then appears on the screen, only the line is now Xavier -4.5. Spanky sees it from his screen, wherever he is, because he texts me “They disrespected you.”

What Spanky means is that my bet, which was likely the only bet they took on a Tuesday morning on that particular NIT game of any amount, let alone for $5,000, should have caused them to move the line in such a way as to attract bets on the other side. They should have given Toledo MORE points, not fewer, to get someone to take the other side of the game and balance out my bet. Instead, by moving the line in my direction, they were trying to entice me to bet more! I clutch my backpack and go back up to the counter to speak to the manager.

“I noticed you guys moved the line. Can I bet it again?”

He punches it into the computer and waits for word from the trading office in Las Vegas. “You’ve got a bet,” he says. I hand him $5,000 more. When I return to my seat, the game flashes again, and this time the line goes back to -5. “Bet it again,” Spanky texts. Back to the counter, and another bet approved. I now have $15,000 on Xavier against Toledo, which seems, well, mind-boggling. This time, the line moves to -5.5. “That’s enough,” Spanky texts. I sit back down, relieved to not wager any more of our money on a game where I couldn’t tell you either team’s mascot, let alone what city the college I was betting on was located in.

I’m soon informed that my new bet limit is $1,000 on everything. With a 1 percent hold, that means we were theoretically earning $10 on every bet. “Next stop is out the door,” Spanky texts me.

“They just assumed you were a whale sucker,” Alan Denkenson tells me later. “But most people are limited after four bets. You can keep sending people with new names and fresh money. But if you laid 5 on a game and it closed 8 you’re guaranteed to be a sharp.” This means that if I got my bet in on a number that was far more favorable to me than the number the bookmaker eventually settled on when the game tipped off, the bookmaker would figure I was a step ahead of them, and they’d be leery of my action.

What I didn’t know was that while I was betting Xavier at Ocean, Spanky was betting Toledo everywhere else. Only he wasn’t betting $5,000. He was betting much smaller amounts. Still, it wasn’t a game a lot of people were betting, and his action always causes a stir. Instead of reacting to my bet, William Hill reacted to the lines moving at all the places Spanky was betting, from -5 to -4.5. “They said, ‘Fuck you, Dave, come and get it,’” Spanky says. “So we said fire away -4.5 everywhere.”

Spanky’s model thought the game should have been Xavier -7.5. When I left the casino the line was already at -7.

The William Hill Sportsbook at Tropicana Atlantic City
Getty Images for William Hill US

One of the people Spanky partnered with in 2011 to make bets for him was a bookmaker in Allentown, New Jersey. Unbeknownst to Spanky, the man was also caught up in an investigation by the New York Police Department’s Organized Crime Division because of his connection to someone dealing illegal cigarettes out of Delaware. Investigators overheard Spanky talking to the bookmaker about money he was owed. “They thought, ‘This guy Spanky must be bigger than him,’” Spanky says. “I wasn’t. I was just a bettor.” But soon the investigators were also tapping Spanky’s phones, believing him to be a major illegal bookmaker.

Through those wiretaps, investigators traced an intricate web of bookies and bettors that stretched across the globe, and involved both illegal street bookies and a major Wall Street financial firm, Cantor Fitzgerald. They built a major case that they called “Operation World Wide Wagers,” and in October 2012 they started making arrests. They came through Spanky’s door with their guns drawn. They took him away in handcuffs. They seized $700,000. In all, they arrested 25 people in five states.

Spanky says he was a victim of a misunderstanding about how his business worked, that he was mistaken for a bookmaker when he was merely a bettor. He was placing bets through so many accounts and with so many partners, often with bookmakers who themselves were operating illegally in the United States, that it created a confusing web of cash moving back and forth among many parties on both sides of the law. In all, Spanky was charged with enterprise corruption; fourth-, third-, second-, and first-degree money laundering; first-degree promoting gambling; and fourth- and fifth-degree conspiracy.

As Spanky and Mike sat in jail, they contemplated their future. Perhaps they should get out of the gambling business. Mike suggested they open up a hot dog stand. Spanky says he agreed to plead guilty to a felony charge of “promoting gambling” in order to keep himself and Mike out of jail. He took his first break from betting in 12 years. He joined a touch football league. He played in board game tournaments. Eventually he wondered what he was doing with his life. “What are we doing?” he asked Mike. “This is our fucking business. This is all I know how to do.” So six months later they went back to work.

It wasn’t easy building things back up. His Princeton guys got scared and quit. His betting partners worried he was hot, maybe working with the feds. And his wife was terrified the police might come kicking in the door again. She asked him to promise it would never happen. “I can’t promise you that,” he told her. What he could promise her was that he would live his life out in the open. There would never again be any doubt which side of the counter he was on. “I live life like every phone call is tapped,” he tells me. “Now it’s crystal clear that I’m a bettor. I’m no longer living in shadows.”

Over the next few years, Spanky and Mike worked hard to build their business back up. They started betting again, building their bankroll back up. They had a few good football seasons. Things appeared to be getting back on track for them. And then last year the Supreme Court issued the PASPA decision, which paved the way for legal, regulated bookmaking in New Jersey. It was like a dream come true. The work that Spanky had done his entire life—work that once required him to hide his identity, to meet people in back alleys to trade sacks of cash, work that led to his phones being tapped, his nest egg being confiscated, and his reputation dragged through the mud—he would finally be able to do with his head held high. He’d do business with bookmakers who were licensed and regulated and, best of all, based right in his home state of New Jersey.

The first sportsbook to open in New Jersey was at Monmouth Park racetrack in Oceanport. Showing astute foresight, William Hill signed a deal with Monmouth Park in 2013, a full five years before the PASPA decision, at a time when few people were predicting the law would be overturned. Spanky knew William Hill’s reputation out in Las Vegas. He didn’t think there was any hope that he would be allowed to bet there. But Mike thought it was worth a shot. And if the sportsbook didn’t let him bet, they could film it, put it on Twitter, and expose William Hill for kicking out winners. Spanky didn’t know much about Twitter, but he said, “Fuck it, let’s do it.”

The first day Spanky arrived at Monmouth Park, the place was packed, and people were betting with both hands. To his surprise, the company let him bet $5,000 on first-inning baseball props. The second day the crowds hadn’t subsided, and everyone was betting on World Cup games. Spanky figured he’d press his luck, and asked to bet $50,000 on a game. The company told him it could take “only” $10,000. “This is insane,” Spanky thought. By Day 3, Spanky stopped thinking of it as a stunt and started thinking, “Maybe I can actually make some money here.” Spanky considered that William Hill in New Jersey might actually be different than it had been in Nevada. Could it be possible that bookmaking in New Jersey was going to be a return to the good old days? No sooner had Spanky let himself start daydreaming about getting to bet $10,000 a game that a manager approached him with the words he had been waiting to hear. “Can I talk to you for a second?” Spanky motioned for his guy to start recording the conversation. The manager told Spanky the company wouldn’t accept any more bets from him. Spanky interrogated the manager for the video. “So you’re kicking me out because I’ve won too much, and the action is too sharp?”

“More than likely, yes,” the sportsbook manager sheepishly replied.

From then on, Spanky was a man on a mission. As each new sportsbook opened in New Jersey, Spanky showed up. Each time he negotiated bet limits. Each time he was welcomed by the sportsbooks with open arms. Casinos usually salivate over players willing to bet large amounts, wining and dining them and putting them up in free suites. The new sportsbooks in New Jersey were no different. “DraftKings rolled out the red carpet for me when I was losing,” he tells me. “Steak dinners and rooms. Four weeks I was there. Once I started winning, I had a big weekend and held 32 percent, they cut me off.” Eventually every sportsbook told Spanky it wouldn’t take any more bets from him. Sometimes it was after a week of taking his bets. Sometimes within a couple of days. Each time he recorded it and posted the videos on Twitter. Each time his followers grew, cheering him on. After Pennsylvania legalized bookmaking and Parx Casino opened its sportsbook, Spanky tweeted that he was planning to go check it out. Parx mailed Spanky a letter telling him he wasn’t allowed to set foot on the property, later citing on Twitter Spanky’s “behavior issues & unauthorized video recordings of other sportsbooks.”

Not every sportsbook in New Jersey has banned Spanky. The Hard Rock, the most recent sportsbook to open in Atlantic City, welcomes his action. Joe Lupo, the Hard Rock’s president, comes from the world of sports betting. He was the manager of the famed Stardust sportsbook in Las Vegas in the 1990s and early 2000s. “If you were a real gambler at that time you knew you could get a bet down at the Stardust,” Lupo tells me. “We gave everyone a fair opportunity. It was a player’s sportsbook.” Today the Hard Rock’s new sportsbook stands apart from most other New Jersey sportsbooks. While others are run by large international conglomerates pooling money from bets taken all over the world, the Hard Rock is backing the sports bets it takes with its own money. It’s old-school, but it’s the only way Lupo knows. “We actually welcome the sharp bettors,” he says. “I believe if you hang a line anyone should be able to bet it.”

Johnny Aitken at PointsBet is also hoping to make a big splash in New Jersey by going against the grain and allowing sharp players to bet big, and he hopes it will even help give his book an edge. “We’re not naive enough to think every time we put up a price it’s 100 percent correct, and we very much respect the sharp bettor’s information,” he says. “We more often than not maybe change our price to respect that money.”

But PointsBet and Hard Rock are exceptions, and the industry leaders in New Jersey are based largely in Europe. Spanky decided he’d confront those industry leaders head-on in April at the Betting on Sports America conference at the Meadowlands Exposition Center.

The three-day event was a trade show for the technology and data companies, many of whom are European, that hope to break into the fledgling American market. Data and technology are the driving forces in sports gambling now, more closely resembling a bizzaro version of Wall Street. Bookies are now traders. Bets are positions. Instead of talking about fumbles or points or vig or juice, you hear talk of Python and stacks and hold and risk. “There is a school of thought that ‘Software is eating the world,’ and sports betting is not exempt from this,” says Pinnacle CEO Paris Smith. “Technology is fundamentally disrupting every industry with advances in big data, machine learning, and artificial intelligence. Old-school bookmakers are being replaced by algorithms that do the work once done by armies of traders, whose jobs are now to oversee the systems that power the trading floor.”

“I can’t tell you how frustrating it is when they have these panels and they’re all MIT guys, they studied economics or statistics or whatever, and they overestimate the risk,” Vic Salerno says to me as we watch the crowds go by in the conference hall. “It upsets me because they call their bookmakers traders. Well, I call them traitors.”

Meanwhile, pictures of football and basketball players decorate the exposition center, subtle reminders of what is at the root of all this “trading.” I am struck by how little discussion there is of actual gambling. Gambling, it seems, is only what the customer is doing. Gambling is for suckers. For this new generation, bookmaking isn’t gambling. It is simply finance. And it must never, ever lose money. Not $20,000, not $20.

“Now the guys running the sportsbook have fancy degrees on the wall but don’t know anything about the pulse of the sports bettor,” says Bill Krackomberger. “I’m a throwback. I’m an old-school guy, last of the Mohicans. Now these guys who run these casinos do not even gamble. They’re just looking at the bottom line.”

During a panel titled “Pioneering Spirit,” the CEOs of a number of new operators, including Joe Asher, the CEO of William Hill’s U.S. operations, talked about their vision for the future of the industry in the United States. Jon Kaplowitz, the head of interactive for Penn National Gaming, which is partnered with William Hill, was asked about their risk management strategy. He joked that his strategy was, “Joe [Asher] with a baseball bat running the sharps out of our casino.”

During the Q&A, Spanky takes to the microphone, and Asher immediately drops his head as if he knows what is coming. Spanky asks, “Jon, you mentioned Joe has a baseball bat trying to kick out sharps from the casino. I myself have personally been kicked out of all of your sportsbooks, as well as several of my colleagues, for the action being quote-unquote too sharp. And I was wondering if there was a possibility that you guys were going to practice effective risk management and instead of kicking out customers, to welcome all customers and having people, if they win, they’re still able to bet in your sportsbooks.”

After some uncomfortable snickers from the audience, and an answer from Kaplowitz about how he has to manage between giving customers a great experience and making a profit, Asher grumpily responds. “This whole idea of people getting kicked out for winning is so overblown in the media and is such a distortion of reality,” he says. “The stuff you read out there on Twitter or that makes its way into some press articles is just completely fanciful.”

The exchange was devoid of fireworks, but across the conference people who weren’t at that panel were gossiping about what they heard about the exchange. Later that evening, one conference attendee tells me he heard Spanky threatened to go after Asher with a baseball bat. When I tell him what Spanky actually said, the man seems a little disappointed.

But Spanky’s presence at the conference did seem to make an impact. A CEO and a number of executives from companies who had banned Spanky approached him and told him they’d like to talk to him about how they could work something out. And other gamblers were patting him on the back and thanking him for taking a stand against the greedy corporations. Long gone were the days of bettors grousing about his steam play, of calling him a bottom feeder. Spanky had become the sharp player’s shop steward; a gambling folk hero.

Back at the Ocean, where I’ve been limited to $1,000, Spanky tells me I should quit. While it still feels like a fortune to me, he explains that we really only expect to make about $10 on each of those bets, and the risk may not be worth it to me. If we keep going, he assures me, my limits will be cut to $300 before long. And after a couple of more days of betting like this, I’ll likely be cut off completely. But I’ll have to take his word for it.

We have dinner that night at Chef Vola’s, one of Atlantic City’s hidden treasures, and a restaurant where civilians have to wait a month or more to get a reservation. Spanky Kyrollos, however, knows a guy, and we get in no problem.

We feast on veal and fish, celebrating our success, though I haven’t cashed a single ticket. All of the bets I made were either for games the following day or games currently being played. But Spanky doesn’t care. He doesn’t sweat the games. “Why put myself through that? My work is already done.” He just checks the numbers when he gets to his office each morning to see how he did.

I wonder aloud to Spanky why we are celebrating when we haven’t won any money. “It doesn’t matter if we win or not,” he answers. He shows me a screen on his cellphone with the point spreads for all of the next day’s games on it. “We beat the line in every single bet today,” he says with pride.

The couple at the table next to ours interrupts Spanky. They recognize him. Spanky is gregarious in chatting with them. If there is such a thing as New Jersey charm, Spanky exudes it. They’re visiting Atlantic City for a birthday, so Spanky gives them a nice bottle of wine. Then he jumps back in without missing a beat.

“This is why I do this,” he says. “It feels so fucking good, even after all these years. I don’t need the money anymore. I love the challenge. It’s a game. And when you beat the line, that means you won. That’s better than winning money. That’s better than sex.”

I don’t tell Spanky that for my small part in our arrangement, beating the line is better than neither of those things. But I do admire his pride in craftsmanship. It’s infectious to see someone treat gambling in this way, as a cerebral challenge, bookmaker and bettor locked in a battle of wits. In this particular battle, his foe is so vastly powerful and wealthy that I can understand his enthusiasm for this small victory. I even root him on. But as a minor partner in this endeavor I also feel it’s much easier to take such a romantic attitude about gambling when you can afford to lose the money. Or it could simply be that deep inside his heart he is that increasingly rare creature in this modern world: a true gambler.

Spanky will say that for him, this isn’t recreation, this is his job. But he’s clearly having a lot of fun. Bookmakers will say Spanky doesn’t play fair, he bets only when he has the best of it, but he’s clearly taking some risk. After all, Xavier could still lose. I took no solace in beating the line, in being sharp. Deep inside my own heart, I was no better than the bookmakers—I was terrified of the risk.

Late that night after dinner, as Spanky and I walk back through the casino to our rooms, he stops suddenly in front of a slot machine. He pulls out his phone, does a few calculations on his spreadsheet, then looks at me and smiles. He pulls out a wad of bills and peels off a 20, then waves me over to join him. I do not yet know that the following day the Xavier Musketeers will defeat the Toledo Rockets by 14 points, nor that the bets I made that day would end up winning just over $30,000, of which $300 would be all mine. Still, I have already celebrated. I have eaten veal and fish. I feel strangely proud and good. I pull out a 20 of my own and join him at the machines.

David Hill is currently writing The Vapors: A Casino in Southern Gothic for Farrar, Straus & Giroux. His website is davidhillonline.com.

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