It was an unusually pleasant day in the desert. The temperature in Las Vegas was 80 degrees with a cool breeze. Alan Denkenson was inside, hunched over his computer in his office, obsessing over weather reports.
"I have a niche thing with weather that I do," he tells me without turning around from his monitor. "When the wind blows in, that's six-and-a-half. When it blows out, that's twelve-and-a-half, easy." I have no idea what any of these numbers mean, but he doesn't care to explain. He just continues to scroll through spreadsheets.
Once upon a time, Alan "Dink" Denkenson was one of the biggest bookmakers in America, having transformed the small bookmaking operation he ran from the grandstands of the Meadowlands into a national organization with offices and staff. When celebrities and high rollers like Isiah Thomas wanted to make a big bet, their bookies called Dink to lay off the action. None of it was legal, and after three arrests and a year in a halfway house, Dink decided to give up bookmaking and try his hand at life on the other side of the equation, and within the boundaries of the law. So he moved to Las Vegas and became a professional gambler.
That was over twenty years ago. For a time, Dink was one of the most successful gamblers in Las Vegas. His specialty was hockey, where he was known to wager as much as $5,000 a game. His bets would move the lines all over the country. His notoriety as a Queens bookie with a rap sheet was long forgotten, and in Las Vegas he lived a respectable life as a sharp bettor. His status as Las Vegas legend was cemented in 2012 when Bruce Willis portrayed him in the movie Lay the Favorite.
But times have changed in Vegas, for Dink and other old school professional sports bettors. The game has been taken over by a younger generation with backgrounds in finance and a knack for analyzing data and markets for value. The information age has made both sides of the betting market smarter, and the result has been tighter lines and fewer opportunities to find value. "Nothing is stealing anymore," he says. "In the '70s and '80s, a college education put you crushingly ahead of everybody out here."
In order to eke out a good living today, Dink needs to make lots of smaller wagers and spread his risk around. He's gone from an average bet of around $3,000 a game to something like $500. He's proud that he's still standing—"A lot of friends I've had over the years have gone broke and moved on," he says—but is he still a winning player?
"I better be," he says. "I haven't had a job in over 40 years."
These days, Dink is far from a high roller. He lives in a modest home in a gated community in South Las Vegas with Gayle, his wife of twenty years, and Irving, their rescue schnauzer. Hunched over his computer at his desk, the 62-year-old Denkenson doesn't look his age. He's over six feet tall, dressed in a Denver Rollergirls Roller Derby T-shirt, and has an incredible head of curly graying locks. He has a sweet, almost childlike smile. He rarely leaves this office. Day in and day out he sits beneath a wall of framed photos of racehorses and watches four or more games at a time on a wall of television screens, scanning his computer monitors for the latest box scores, line moves, and, of course, weather reports.
I visited him during a big week for Dink, Inc.—Kentucky Derby week, one of the most gambled-on sporting events in the world. Last year, people bet over $137 million on the race. By comparison, the 2015 Super Bowl took only $119 million in legal bets in Nevada. Nevertheless, horse racing has never been a particularly popular bet with professional sports gamblers. They dislike that the odds will continually shift after they bet, eliminating their ability to take advantage of bad odds, and they dislike that the house keeps as much as 25 percent for itself.
Dink is one of the few pros who puts a sizable portion of his bankroll into horses. He has an affinity for the sport, having first wet his gambling whistle at the racetracks of New York. He also believes that horse racing offers gamblers a unique intellectual challenge. Races have literally hundreds of variables to consider, betting pools are frequently loaded with dead money and under-valued propositions. Most important, unlike in sports where most bets are nearly even money, a smart player can bet a little to win a lotin horse racing.
"The elite horseplayers make much more money than the elite sports gamblers," Dink says. "In sports, you just try to win 53 percent of the time. In racing there is a much bigger reward."
He estimates that top horseplayers are putting in 50 to 60 hours a week at the job: nine hours a day on handicapping and another three hours a day on planning their wagers. They monitor dozens and dozens of data points at racetracks all over the world and they rarely bet on anything else; their bandwidth can't handle much more. And all of this is required, Dink says, to have a shot at beating the enormous track takeout. "If the takeout was 5 percent, I'd quit sports and bet nothing but horses."
But the Kentucky Derby is far from your usual horse race. It's twenty of the top three-year-old horses in the world racing on dirt for a mile and a quarter, a longer distance than any of them have run before. The depth of talent and the uniqueness of the race make it an incredibly difficult puzzle to solve, but because there is so much money spread among so many different outcomes, the payoff for getting it right can be huge.
This year, however, Dink isn't feeling it. "I don't have an opinion on the race," he tells me. "It's too hard this year." That isn't enough for him to take a pass, though. It's still the goddamn Kentucky Derby. And Dink has two things he thinks gives him an edge, even in a race that's so tricky to figure out.
The first is the head-to-head match-up bets. A number of casinos and offshore bookmakers offer bets on match-ups between two horses in the race. You pick one horse to bet on and if it finishes anywhere ahead of the other horse—even if it doesn't win—you win the bet. Dink likes the match-up props because they have 5 percent juice instead of the 15 to 25 percent you have when betting through the racetrack pools. The lines are set the same way they are for the sporting events that comprise Dink's bread and butter. And the number of players he's likely up against in these bets is smaller. "There's maybe four people looking at these lines, and I probably know all four of them," he explains. "This is just something I do well. I don't do golf matchups. I'm good at this."
The match-up prop was the brainchild of Johnny Avello, the sportsbook manager at the Wynn Las Vegas. He's widely respected as one of the top bookmakers in Vegas. While many casinos choose to buy their sportsbook lines from a subscription service, Avello continues to produce his own lines every single day, including head-to-head match-up props on horseracing on the weekends.
"A lot of places won't offer these props anymore because they don't do much horseracing business," Avello told me. "But I grew up around horseracing. I love the sport. My customers love the sport. And these younger players, who maybe don't know the sport as well, they like these props because it feels familiar, like betting a game."
While the Wynn makes their own match-ups, most of the Las Vegas casinos will follow Costa Rica International Sports, an offshore sportsbook. Every year they make lines on the largest number of match-ups. But at noon on Thursday, a full 24 hours after the post positions for the race were drawn, CRIS still hasn't posted anything.
"Where are all the matchups?" Dink barks, growing restless. He stands up at his desk. "I'm going to pilates." He gives his assistant, an attractive young woman named Mary Sutton, a large stack of hundred dollar bills, and instructs her to give the money to someone named Robert to bet some lines at the Wynn. He changes into sweats, hops in his KIA, and speeds off to clear his mind and heal his body.
Sportsbooks in Las Vegas do not like professional gamblers. You'd think they would, since professional gamblers are their most loyal customers. But a bet in a sportsbook is essentially a bet you make with the house, and sportsbooks don't like making bets with players that can beat them. What allows a professional sports better to make a living isn't just being really good at predicting who can win games; the difference is their skill in figuring out when a line is off a little bit. Making a bet on the right side of a bad line is what gamblers call having "the best of it," and it is everything to them. It doesn't guarantee they will win a bet. It just guarantees that, over the long run, they will win more money than the other side. They don't make bets on games where they favor one side to win over another. They make bets where they think the price they are being offered is better than it should be. And when they find these situations they like to bet as much as possible.
Sportsbooks combat this by placing substantial betting limits on players they know are winning professionals. Or they will limit the number of bets those players can make in a day. Or they can refuse to take their bets at all. Dink, for example, is simply barred from placing bets at any Caesar's properties. At the Treasure Island, he can't bet more than $300. At the Wynn, his limit is $1,000, which reflects a more permissive attitude toward professionals on Avello's part.
"I respect those guys," Avello says. "I always give them a bet. But sophisticated players have limits. If I didn't make limits for them, they'd put us out of business."
These limits have put a significant damper on Dink's earning potential, but he has ways around them. In the old days he would employ "runners" to hang out in all of the casinos. He even had a little old lady who sat in a casino in Reno for him all day long. He would call them up, get the lines, and tell them what to bet for him. Today, having a runner, or paying someone to place bets for you in a casino, is against the law. So Dink instead takes on a partner, someone who isn't a professional gambler and is unknown to the casinos, and has his partner place all of their bets. Robert, the man to whom Mary was delivering that stack of Dink's cash, is Dink's partner this week. Robert's in for 10 percent of Dink's action, win or lose, and since Dink is doing all the homework, Robert is doing all the legwork.
When Dink returns from pilates, he calls Robert on the phone and asks him where the line is at now. Robert tells him that the line has moved, and that he spotted the partner of a well-known professional horseplayer in the sportsbook. "Is he betting or just hanging?" Dink asks. He's betting.
Dink hangs up the phone. He's not sure what to do. The man who made the bets on the props is someone Dink knows is much sharper than him at the horses. But if he's reading the line moves correctly, the other player is betting against what Dink wants to bet. "I have to get Emily on the phone."
Emily Gullikson is the second edge Dink has over the competition this week. The 35-year-old former straightedge skateboarder and roller derby star is an unlikely character at a racetrack, yet today she is killing it on the horseracing handicapping tournament scene. She and Dink met through mutual friends, and they entered a horseracing tournament together in January where they won an entry to the $1,000,000 National Handicapping Championships. Dink has relied on Emily for her advice ever since.
What makes Emily different from most horseplayers isn't just that she listens to death metal. Emily's knack for picking horses is the result of hours of hard work; she watches morning workouts, taped replays of races, and keeps her own private stats on countless horses and races around the world. She is part of a team of horseplayers who have developed software called OptixEQ that analyzes races using their methods. Emily lives and dies by OptixEQ, and she has turned Dink into a believer. In exchange for sharing her information and opinions with him, he cuts her in for a 10 percent freeroll of whatever he wins—she doesn't have to put up any money if he loses. But he's having a hard time getting her on the phone.
"Emily has a dark side," he explains as he waits for her to pick up. "She can't keep plans. She's disorganized." Dink has been trying to get Emily on the phone all day long, but her phone keeps going to voicemail, and her voicemail is always full. Dink is nervous to make any moves without her. "What can I do?" he asks. He dials up Robert.
"Get me a dime on Whitmore over Sudden Breaking News at plus twenty, a dime on Exaggerator minus thirty five over Gun Runner, a dime on Exaggerator minus forty five over Outwork, a nickel on Tom's Ready minus thirty over Trojan Nation, a dime on Outwork even over Creator, and a dime on Mor Spirit minus ten over Mohaymen." He listens to make sure Robert got the bets right, then hangs up the phone. He shrugs. "I don't love it," he says, defeated. "But what can I do?"
Back at Dink's house, Robert hands over a stack of money and a stack of betting slips, including the $5,500 in prop bets he made over the phone. Dink takes the day's losing baseball, hockey, and basketball tickets and places them on top of a pile of losing tickets about six inches tall—the losers for 2016, "in case I ever get audited." He figures the average ticket is about $700, and there are at least a few hundred in the pile of shame.
As Dink goes to put the prop bets with his other live tickets, he starts searching frantically for a $1,000 winning baseball ticket he's misplaced. He, Robert, and Mary tear the office apart looking for it. Mary and Robert laugh at Dink, but he seems unamused. The panic subsides after Dink finds the ticket folded up in his wallet. Robert and Mary crack up. "I really worry about this," Dink says, stone-cold serious. "I'm losing my focus. I'm not as sharp as I used to be. I worry it's affecting my gambling."
That night, Dink and I meet up with Waz, a 34-year-old professional gambler that Dink has mentored and who he considers one of the "truly elite" gamblers in Las Vegas. We have dinner at a pizza place near KSHP AM 1400, where Dink is hosting the Eye On Gaming radio show later that night. Waz and Dink are friends, though Dink doesn't typically like to hang out with other gamblers. He prefers friends that share his non-gambling passions like music and wrestling. "Most gamblers never want to talk about anything other than gambling," Dink says. "They don't have anything else going on in their lives."
Waz has been on a roll lately, and Dink encourages his optimism. On his own future, though, Dink is pretty bearish. "I always think variance will kill me," he says between wolfing bites of pasta. "If a horse breaks bad, I know it's going to be mine. I feel like I'm always taking even money on things that come down to fate."
Waz tells me that Dink is known for his gloomy disposition and self-flagellation. Waz says that downswings and variance are typical; his own career began with an unusual upswing, which he admits made it easier to keep his wife onboard with his attempt at being a full-time pro. "If I had started on a downswing—and I've had plenty over the last six years—I don't know that she would have been OK with it."
Dink's own marriage of two decades is now falling apart. He and Gayle are in the midst of finalizing what he describes as an "amicable divorce." He isn't sure if it's because of his losing or because of his inability to handle losing well. "I think my pessimism is getting the best of Gayle," he admits.
The next morning is Kentucky Oaks Friday, the day before the Derby, and CRIS still hasn't posted the prop lines yet. Dink sends Robert out to scour the strip for other props (and assorted baseball and hockey bets), and I tag along.
Robert loves Vegas. He and Dink grew up together in New York and ran in similar circles of gamblers around the racetracks in the 1980s. "Back home they tried to put us in jail for making book," he tells me. "Out here, being a sportsbook manager is like one of the top jobs you can have. It's respected."
Our first stop is the Wynn, where the sportsbook is already unusually crowded for a Friday morning. Despite what they say about horse racing being a dying sport, Avello says that on big race days like this he always gets a packed house. Robert greets another professional gambler standing in the back. "Nowhere to sit today?" Robert asks. The man shrugs. "Even Larry King is here," he says. The television host is camped out in the third row eating his breakfast and betting horses with both hands.
Robert and the other gambler are in a heated discussion about the line on the Canelo fight when Dink calls. After hearing the lines at the Wynn, he orders us to leave and go to Treasure Island. We sprint across the casino, out the doors onto Las Vegas Boulevard, and across the overpass into the Treasure Island sportsbook. There, Robert calls Dink back and reports on the props for the Kentucky Oaks, the race for three-year-old fillies that serves as a sort of companion for the Derby every year.
"Royal Obsession is minus fifteen," Robby says. "It was plus fifteen this morning!" Dink yells through the phone. A thirty-point swing in just a few hours. "Don't bet it," Dink says. "Someone beat us to the line."
After making a handful of smaller $300 props and game bets, we head back to Dink's house. He's unhappy. He's lost three match-up props in a row already today. "But the odds justified the lines," he says matter of factly. "It's just market reading. I watch the lines and I can see them all moving against the same horse, I have to respect that, even if I don't have an opinion on the race. I have to respect the money." He places the three tickets on the pile of shame.
The Kentucky Oaks is on all four screens on Dink's office wall. Dink has made some big prop bets and has a lot of money on the race in what he describes as a "friendly contest" with a buddy of his. He shushes everyone as the horses come around the far turn into the final stretch and points out the horse that he needs to win as she surges to the front of the pack.
"Oh, you got this," I say.
"Don't..." Dink begins, a look of horror on his face. I turn to Mary and Robert and notice similar looks on their faces. I realize I've committed a mortal sin. Another horse catches her in the stretch. Then another. Then another. It looks like she's running in reverse. Dink slumps back in his chair. The air is sucked out of the room.
"Well, David learned an important lesson today," Dink says. He turns to his computer monitor and starts furiously clicking. Robert and Mary say nothing and won't look at me. I apologize profusely. I know I didn't make that horse lose, but I also know that I messed up. It's superstition, sure, but still, there are rules. What would gambling be without rules? Just variance. Chaos. Madness.
Later that afternoon, the lines are finally posted at CRIS, and there are a lot of them. The seven favorite horses in the Derby are all paired up with one another in every possible combination. Dink gets Emily on the phone. She's all business, no small talk. "Did you look at the Optix I sent you?" she says, referring to the data from her handicapping software. Dink pulls up a graph on his computer showing various squares and triangles of different sizes scattered across the graph. They go back and forth discussing the graph.
"Outwork is quadrant 1 and Creator is quadrant 4," Emily says. "I can't compare them because they aren't in the same quadrant."
"There are eight and a half horses in quadrant 1!" Dink replies.
"People think that these horses are closers but they've won at six furlongs," says Emily. "They're just being lazy."
"I'm trying to bet horses that are sitting in third, fourth, and fifth in the props. If they are sitting third through seventh they will beat the deep closers," Dink says. "That's my contribution to the props. If I'm wrong then we'll lose every prop."
Eventually their banter turns to debate, with Dink referencing the opinions of other handicappers he knows who disagree with Emily's choices.
"You put a lot of stock in other people's opinions," she says curtly. "I don't do that."
"I value your opinion as much as theirs. You should be flattered. Some of these people make a lot of money betting just on horses and have for a long time."
"Maybe you should go start your own analytics company," she replies.
"I'm the first to admit I'm not as good as you at horses," Dink says, a bit wounded. "I take your point. In hockey I trust myself above all others, but this is your number one thing. Everyone I know has different opinions on every horse."
"Well, yeah," Emily says, dumbfounded.
"Look. This race is killing me and I need your help."
After they hang up the phone, Dink calls Robert. He decreases the bets he previously made that Emily didn't like and increases the bets she did. He makes a few more that she had no opinion on. He gets off one bet in particular, his prop on Exaggerator, and takes the other side. Robert tells him the lines are all moving against him, the money is getting bet on the opposite side. Dink doesn't like to hear that, but he tells Robert to bet it anyway. By the time he's done, he has over $8,000 in head-to-head match-up bets on the Kentucky Derby.
"I just have to trust her opinion even though I personally disagree and I'm against the money here," Dink says. "That's how a true partnership works. If I'm just going to second guess her and bet what I wanted anyway, what would be the point of working with her at all?"
Dink finishes the day by balancing his books. He rebounded from his loss on the Kentucky Oaks and wins around $2,200 for the day. He closes the ledger and settles in to read tomorrow's weather reports before bed. "Might rain," he says with surprise.
Derby Day starts early in Las Vegas. Since we're on Pacific Time, the first race goes off at 7:30 AM. By noon Dink has already made several bets on undercard races and even more bets on props. "My head is spinning already." He spends the day calling fellow gamblers around the country seeking out their opinions. Some are cagey, others less so. He makes one last call to Emily to make sure she hasn't changed her mind on any of the props. She again expresses concern that Dink isn't trusting himself enough. "I let my ego go a long time ago," he tells her. "I'm quick to change my mind. That's just how I do my business. I'm investing in your opinions."
"I just hope they're right," Emily says.
They get off the phone and Dink calls Robert at the Treasure Island. He hears how the lines are continuing to move against him. "Well," he says, "it's just me against the world."
At 2 PM, the pre-Derby festivities begin. At the Wynn sportsbook, Johnny Avello hands out roses to all the women on hand to watch the race. Dink watches on television at his office as the crowd of over 165,000 people at Churchill Downs sing "My Old Kentucky Home," huddled under tarps to shield themselves from the sudden cloudburst. Dink starts to worry about what a muddy racetrack could do to his handicapping of the race. A weather alert crawls across the bottom of the television screen. "Is that for Kentucky or for Las Vegas?" I ask. A thunderclap outside answers my question. Moments later the rain is pouring, both on the crowd in Louisville and on the street outside Dink's house. "Now I wish I had Exaggerator," Dink says. "The rain will probably make the pace too fast."
As the horses walk down the track in the post parade, he sighs. "This is the most unhappy I've ever been going into the Derby."
There are commercial breaks that last longer than the entirety of the Kentucky Derby. The entire race lasts only two minutes, but to those who have money on the race, it can feel so much longer—dreamlike, outside time. For those who have handicapped the race to excess, it is all over at the first quarter of a mile. If the right horse doesn't get the right break, if the wrong horse is setting the wrong kind of pace, if the horses in third, fourth, and fifth aren't the horses you though would be third, fourth, and fifth, then all your work is for naught. In the Kentucky Derby, you're likely to be wrong more often than you're likely to be right about these things. Twenty horses is an insanely large field, and there are hundreds of things that can go wrong and blow your entire wager, make a mockery of all of your charts and graphs. Your order will give way to chaos, and chaos will rule the race.
"This is bad," Dink says after the quarter mile. This is after 22 seconds. The pace is too fast, perhaps from the wet track. Dink and Emily's theory that the horses sitting third through seventh would beat the closers isn't going to hold up with a pace this fast. After 22 seconds, he knows his goose is cooked.
"This is very bad," Dink says as the horses cross the finish line a minute and a half later. They are the only words he speaks. He stares silently as the top four betting choices, incredibly, cross the wire first through fourth. That may not seem like an unusual outcome, but it is actually a major surprise for a race like this. And anyway, there is no pride to be had, no gambling badge of honor, in choosing an all-chalk superfecta. That's for grandmas and ten-cent bettors. That's not the kind of thing a real pro would make hay about. Perhaps, if nothing else, there is some consolation there.
Dink watches for a long time, waiting to see the final order of finish of all of the horses to see how his match-ups did. "I either did bad or I did very bad," he remarks. He puts on his reading glasses to get a better look at the saddlecloths of the horses as the finish replays in slow-motion. "No! Look at that! By a nostril!" Dink takes off his glasses and drops his head. "God, I got wiped out."
When all was tallied up, Dink lost $4,500, his second worst result on horse racing props ever. He won four bets and lost six. The six he lost were for a thousand dollars apiece. The four he won were for $500 or less. They were also the only four bets he made that Emily disagreed with and didn't want a piece of. She was wrong on every bet, including the two Exaggerator props he switched after talking to her.
The rain outside was slowing down to a drizzle, so Dink and I took Irving for a walk to the park to decompress.
"I don't want to knock her. It's one race," Dink says. "My business is networking with people who are good. She's good. She's better than me."
We walk across a rock-filled creek bed to a park with palm trees and no grass. There are children splashing in the puddles like they've never seen rain before in their short lives.
"I've been having a bad year. I'm starting to entertain the possibility that I could really go broke," Dink says, without a hint of sentimentality. "Then again, if I don't go broke there's a 50 percent chance that I'm going to turn 75 and be making $4 bets in the sportsbook like these other guys. I mean what else am I going to do? Waz can go into stocks, into finance. I can't do anything else. I'm 62 years old and this is all I know."
The rain lets up a little and a rainbow arches high above the Las Vegas skyline as Dink shows me where Gayle plans to move after they separate, a couple of blocks away so they can share custody of Irving. "I need it, though," he continues. "It keeps my mind sharp. I just know that it's important not to let things like losing overwhelm me. There's a lot more to life than winning or losing at gambling."
Back at Dink's house, Emily phones him to apologize. He won't hear of it. "If they ran this race again would you make the same bet?" he asks. "Absolutely," she says.
"It'd make sense if he didn't want to work with me again," Emily tells me later. "I feel terrible because I pushed for this. But that's how I handicap. I can't change how I am." She's right. And, in a way, that's what Dink likes—that she knows who she is and is true to herself. It's a quality that all successful gamblers share, the confidence to bet everything on themselves, and the discipline to not get shook after a bad result.
"After all," Emily says, "the Derby is just one race. I just turn the page of the Racing Form and get started on the next one."
Correction: An earlier version of this story incorrectly described the Kentucky Oaks as a race for fillies and mares. It is just for three-year-old fillies.