Cigar Aficionado

Steve Cyr has 72 hours in which to make $300,000. If he succeeds, it will require many sessions of high altitude gambling, endless schmoozing, world-class coddling, a bit of lying, a few dozen Super Bowl tickets, and the kind of bad luck that brings even the most resilient high rollers to their knees.

Though Cyr’s fortunes hinge on high-stakes action, he himself is not a gambler. Well, not exactly. He is a whale hunter, a sobriquet for a person who wrangles the industry’s biggest players and sets them up to risk millions of dollars at games in which the long- term odds are hopelessly tilted against them. For this particular weekend, which coincides with the 2003 Super Bowl, Cyr has flown in 16 big players — whales in casino parlance — their 25 guest, and credit lines that total $3 million to the Barona Valley Ranch Resort and Casino, a posh gambling complex that opened near San Diego last December. If they all go through their money (far from an impossibility, but an admitted long shot), Cyr, who consults for eight other casinos in Las Vegas and the Caribbean, will go home with a juicy cut of their losses. “And if they all win,” says the strapping and hyperactive 39-year-old Cyr, “then I go home with nothing.” The subject of a forthcoming book called Whale Hunt in the Desert by Deke Castleman hesitates for a beat and smirks. “But you know that’s not going to happen. It’d be impossible.”

You can’t throw something like this together overnight. In November, when gamblers were still talking about the World Series, Cyr, who cut his teeth by telemarketing vitamins, was already in sales mode. Working out of his home office in Vegas, he called 60 of his best players. Speaking cockily, he initiated a series of conversations that began something like this: “Hey, buddy. It’s Steve Cyr. Listen, you better fucking book your flight to San Diego.”

Well acquainted with the Cyr spiel, the whale bites: “Why?” “I got Super Bowl tickets,” Cyr says.

This is nothing special. If you’re a big players, every casino in Vegas is begging you to come down for the Super Bowl. The whale tells Cyr as much. “Caesars is gonna take me. I’ve already talked to them about it.”

Undaunted, Cyr turns up the heat. “No, man. This is completely different. We’re going to be staying in San Diego, at the Barona. Tell the wife you’re taking her somewhere nice for a change. We’ll limo to the game instead of flying in, put you up in a beautiful villa, and take you out to play golf with a bunch of NFL stars on the best new course in the state.”

Knowing that nobody will seriously commit in November, Cyr lets the idea simmer for a while with his players. Then he tells the Barona that he’ll need 35 to 40 tickets. A couple weeks later he calls his people again. Over the next two months, Cyr sweet-talks their wives with promises of lavish spa treatments in San Diego, woos the men with the Barona’s deluxe invitations (including balls signed by John Elway and other National Football League greats), and talks up the Barona as if it’s Valhalla with Blackjack.

By late December he’s got his lineup of players, but he knows that New Year’s Even can change everything. “Let’s say one of my big guys comes to Las Vegas on New Year’s Eve and blows $3 million around town. Now, suddenly, he’s snapped,” laments Cyr. “He’ll want to come to the Super Bowl, but I don’t want him here. If he loses here, I’ll be last on his list to get my money. Plus, he’ll gamble over his head to try to win back the money to pay the other casinos. He’s what we call a chaser. I don’t want chasers here for the Super Bowl.”

So Cyr spends the first week of January reviewing credit information from Central Credit, the Equifax of gaming. He notices that one of his guys went on a bender, doing particular damage to himself at the Venetian’s blackjack tables. Cyr needs to distance himself from the guy. He makes a phone call: “Hey, buddy. I hear you really fired it up at the Venetian. Yeah, well, there’s a problem with the Super Bowl. They’ve got this weird law in California: if you owe money to one joint, you can’t get credit from any of the places here.” Cyr sounds sincerely sorry and suitably somber, but later reveals, “That’s complete bullshit. But it works for me.”

Another player, one whom Cyr desperately wants, makes an obscene request: He’d like the casino to send a Gulf- stream G-3 jet for him and his friends. Private air transport for a dozen people will cost the Barona $75,000. Initially, the casino balks at this expense. But Cyr goes to bat for his player. “The cost of the G-3 isn’t more than two of this guy’s bets. On top of that, it guarantees that he’ll show u on Thursday night instead of Friday or Saturday. Every casino in Vegas is trying to get him in for the Super Bowl. If we’re set to fly in him and his friends, he can’ back out.” The player, whose $1.5 million line of credit makes him particularly alluring, gets his G-3.

Just days before kickoff, Cyr is still going back and forth with the customer who’s indebted to the Venetian, but now’s he’s dangling bait. “I’m telling him that I’ve got a pair of great seats waiting for him, but he needs to bring us a cashier’s check for 50 grand; then it’ll be fine,” explains Cyr. “The guys asks me if he can get credit from us by paying off the Venetian. I tell him that’d be fine as well. The Venetian doesn’t know it, but I’m working on getting them their money.”

In debt or not, this gambler is more valued than others, evidenced by a different player who also has a decimated credit line. “I’m telling him that we weren’t able to get any decent seats and I don’t want to waste his time. So we’ll take a pass now and do something together in the future.” As Cyr might put it: It’s complete bullshit, but it works.

It seems as if Steve Cyr was born for the game. The son of a Howard Johnson’s hotelier, Cyr grew up in Salina, Kansas. He had every intention of going into the family business, even gong so far as to attend University of Nevada — Las Vegas’ hotel management school with that purpose in mind. But while interning at the Barbary Coast Hotel and Casino on the Strip, Cyr discovered that Vegas was a lot more interesting than Kansas and decided to stay.

Cyr’s first casino job was at Caesars Palace, where he arranged dinner comps and the like for players who were too small for credit lines. One of his big breaks came after he dumpster-dived outside of a competing casino and retrieved a long list off big-betting customers. Employing the garbage-stained information, Cyr used his brash telephone style to steal business and quickly found himself on the path to success. Relentless salesmanship, intense attention to details, the willingness to play dirty, an a knack for making gamblers feel that he was working for them instead of for the casino all contributed to make Cyr one of the top casino hosts in Las Vegas. Cyr, whose best months have netted him more than $90,000, walks a fine line between the house and the suckers. While he and the casino clearly share a financial interest in seeing players lose, Cyr has a way of getting as much as he possibly can for his guys.

“My guys know that I’m not a corporate dick who only cares about keeping a job and getting a bonus,” says Cyr. “I need to make the house happy, but I also make sure my players are happy.”Cyr is a bundle of raw nerves and high energy three nights before the big game. He walks through the suites that his players will soon occupy, making sure the appropriate music is on (Stones for one guy, Eagles for another), tuning the TVs to ESPN, fiddling with lights and leaving a few Cohiba Lanceros in some rooms and big bottles off Grey Goose vodka in others. “First impression,” he says, sliding open a balcony door, “is everything.”

One downside to the Barons is that the casino hasn’t acquired its liquor license yet. The Barona is compensating by placing single-serving bottles of booze in its rooms. Cyr knows that these won’t cut it with his hardest-drinking players, so he’s sending bellhops and butlers out on liquor runs. This way, Cyr can provide full-size bottles that will augment the pewter flasks he’s purchased so that his players can do all the drinking they want, wherever they want. “When people drink, it gets adrenaline going and they play more,” says Tanya Chiodini, Cyr’s girlfriend and partner. A former bartender at the Pink Taco restaurant at Vegas’ Hard Rock Casino, Chiodini initially ingratiated herself to Cyr by providing him with inside info on the bar’s highest-betting patrons.

By Thursday night, Cyr’s biggest player, a man we’ll call Mr. G-3, has checked in. He likes the luxe but comfortable 4,200-square-foot room, with its leather and rustic earth tones, fireplace, jacuzzi and butler. But the player seems to be even more impressed by the Barona’s private gaming room. Unique to the Barona, it’s a sanctum, located below the standard high-rollers room, where the biggest whales can gamble in absolute privacy. Abstract art dots the walls of the comfortable wood-paneled lounge, which features a giant-screen TV and a large table loaded with hors d’oeuvres. Mr. G-3 likes it so much that he’s soon playing blackjack for $30,000 to $50,000 per hand, and spewing expletives as he quickly falls behind by some $400,000. Not quite a third of Mr. G-3’s credit line, but it’s enough to play havoc with the guy’s emotional equilibrium.

Soon after he cashes in for his fifth stack of $100,000 in chips, however, something remarkable happens: Mr. G-3 begins to win. And win. And win. Face cards appear to be his inalienable right and in 30 minutes the $400,000 deficit becomes a $500,000 credit. Knowing better than to push things beyond that, he tips the dealer $2,000 and heads to his room for dinner.

While Cyr is less than thrilled — although you’d never know it from the enthusiasm he shows during his player’s upswing — he tries to look at things philosophically. “Mr. G-3 is here from Thursday through Sunday. When do I want hi to win half a million? Tonight. If this guy is gonna have a run, I’m glad it happened now.” What if it’s still going strong on Sunday? “Then,” Cyr deadpans, “I throw up in a trash can.”

By Friday afternoon, most of Cyr’s players are in town or at least on their way. He’s in constant touch with limo drivers and the players themselves, checking on the progress of the trip, making sure everything is fine (i.e. that they haven’t been hijacked by competing casinos, which is always a possibility), keeping them charged up for the weekend. Because of its private gaming room, the Barona has a Bat Cave-style entry system: limos with high rollers pull into a marble covered garage and players walk a few feet from the car tot he casino, coming in no contact with the low rollers. A special concierge from the private room checks in the high rollers and guys can start gambling before their bags are unpacked.

On Friday night, following a buffet dinner with a group of National Football League legends (Dick Butkus and John Elway among them), players proceed to the private gaming room. Most of them are having a blast and all are wagering anywhere from $500 to $50,000 per hand, though Cyr has some wrinkles to work out. One players insists that he has to “play on the rim” — i.e., that he wants to receive chips without signing markers and with the verbal promise that he will settle up after each session — but the casino isn’t crazy about this. Cyr convinces management to let it go.

Mr. G-3 want to split aces four times, a casino no-no. Cyr has a tense conversation with his bosses, and the Barona relents. “That thing with splitting the aces could have turned ugly and pissed off the whole world,” Cyr says as the action goes on, unabated, behind him. “Once, at the Hilton, Mr. G-3 got mad at me. he immediately packed up his bags and left. If he got mad at me now, he could call the MGM, tell them to pick him up, and they’d have a car here in 20 minutes.”A half hour or so later, Cyr notices a few of his players spacing out at the blackjack table and making smallish bets to a matronly dealer. Cyr momentarily disappears behind closed doors and the old lady is suddenly replaced by a stunning, leggy blonde. “Who would you rather have dealing to you?” h e asks rhetorically upon his return.

The next morning, on the fringe of the Barona’s award-winning golf course, alfresco breakfast is served to the high rollers in attendance. The foursomes get finalized (each group comprises three gamblers and a former professional football player) and the players practice their golf swings. Cyr circulates, too busy schmoozing to eat, chatting up his players, checking on everyone’s progress in the casino, making sure they’re satisfied with their golfing partners and accommodations. Before heading to the practice green, a big player from Vegas checks on Cyr’s progress. He’s well aware that $300,000 is Cyr’s dream for this weekend, and he wants to know how the other gamblers are doing. “They’re doing great,” says Cyr, sounding a little down. “Everyone’s winning. I don’t stand to make a penny off of this whole thing.”

The Vegas player tells Cyr he’s sorry to hear that. I’m shocked to find out that the impossible is happening. “It was total bullshit,” Cyr tells me once his Vegas buddy is out of earshot. “My customers are losing six figures, so I’m ahead $13,000. But Mr. G-3 had another winning night. Now he’s up $1.4 million.”

While the gamblers golf, Cyr and his girlfriend hang around the hotel lobby, working out details. He slips a bellhop a couple hundred bucks and tells him to pick up more big bottles of booze, things about his indebted gambler in Las Vegas (“He never got back to me; that means he never paid the Venetian like he said he would), and works hard to untangle a problem for a player with a $100,000 line of credit who now wants to wager $15,000 per hand. “But we’re not gonna let him bet 15 percent of what the Barona might win,” Cyr says. “You can bet five percent of your credit line, so he needs a $300,000 line of credit. He doesn’t really qualify at that level, but I’m going to get him up to $10,000 a hand. He’ll bet higher than usual, he’ll steam and he’ll get snapped. He thinks I’m doing him a favor.”

Cyr finally gets some down time and he’s contemplating spending the afternoon at the beach with Chiodini. While considering what to do, he acknowledges that there is absolutely nothing spur-of-the-moment about the way in which things here have been scheduled. The casino has invested more than $1 million to woo its players this weekend, spending money on everything from mingling NFL starts to Super Bowl tickets to the G-3, and very little is left to chance. “Today the guys’ wives will be at a spa until 6 pm,” explains Cyr. “Golf ends in the afternoon, so that leaves a good- sized window of time for the guys to fire things up before dinner. Then they have to come down to the casino at around 9 pm tonight to pick up their Super Bowl tickets. Think anybody won’t want to do that? By then it’s too late to go barhopping in San Diego and too early to go to bed. There’s nothing for them to do but gamble.”

A bellhop walks by and acts like Cyr’s new best friend — Cyr reveals that he gave the guy a $60 tip for picking up liquor last night. Then Cyr catches the eye of a parking valet. “Hey, buddy,” he calls out. “I’m ready for you to bring up the monster.”

Monster? “My 360 horsepower Trans Am. It was a toke from two customers. I hooked them up on a million-dollar stock deal. They wanted to give me a Porsche, but I told them that I’m stuck on American cars.”

By Saturday night, the Barona’s private gaming room is crowded, with most of Cyr’s customers putting in their time at the tables, making the kinds of bets that would have them coveted by any casino. Mr. G-3 is still averaging $38,000 per hand of blackjack and showing no signs of slowing down. He’s going so strong that he turns to the NFL Hall of Famer alongside him — a guy betting “only” $500 per hand — and starts slipping him $5,000 chips. “If you win this hand,” says Mr. G-3, “you give me back the five. If you lose, don’t worry about it. How’s that sound?” The retired pro smiles and replies, “I’ll take that deal all night long.”

Mr. G-3, who’s on a monster run but giving the casino very opportunity to win back its money, declares that he wants a Mercedes-Benz before he’ll continue playing. Everybody laughs this off, and he keeps on betting. But, Cyr tells me, “He’s half joking. And if he were losing as much as he’s winning, the casino would give him a car. Wouldn’t you give somebody a $50,000 car in exchange for a million dollars in losses?” Cyr lets this hang in the air for a moment, then he adds, “But we wouldn’t ship the car to him. We’d make him come here and pick it up.”

The next morning, Cyr juggles tickets and transportation and determines who should sit in the 12th row seats and who should be in the skybox, who needs to go by limo and who needs to be part of a large raucous group in one of the casino’s luxury SUVs. Mr. G-3 strolls and seems extraordinarily happy. He’s practically singing as he leads his group of 12 into one of the SUVs. “He’s ahead $2.1 million,” Cyr says, acknowledging that he still stands to make plenty of money (his pay is based on the performance of each player rather than cumulative wins and losses). “What [the casino] doesn’t think about is that he also could have lost $6 million. When somebody complains about a guy like Mr. G-3 winning, I tell them to sit down for five hours and play $38,000 per-hand blackjack and they can see how they do.”

The Super Bowl is a blowout and plenty of Cyr’s gamblers make big wagers on the wrong side, but nobody seems to mind. The field-level seats are fabulous, and in the skybox a waitress keeps the room stocked with food and drink. Anyone who gets sick of sitting outside and watching the game can come in to view it on one of the monitors while fixing a platter of food.

Back at the Barona that night, the gamblers shower, shave and pile into the casino’s steak house before settling down for a final night of gambling. Satisfied with his $2.1 million in winnings, Mr. G-3 cashes out (despite an earlier prediction, Cyr does not throw up into a trash can). Other guys bet their limits, but don’t lose prodigiously enough for Cyr to come anywhere close to his rainbow of $300,000. In the end, only four of his 16 players are losers. This rare bit of luck (good for them, bad for him) is salved by the fact that Cyr now owns these guys at the Barona. For the next year, he will receive a percentage of their losses there, and he is confident that they will return and lose.

Considering that he’s leaving San Diego with an $18,000 take, Cyr admits that he’s a little disappointed. Then he shrugs and says, “Hey, it ain’t $300,000. But it ain’t bad, either. And I got to go to the Super Bowl.