Confessions of the Man Who Wins Big When You Lose It All in Vegas

If you gamble in Las Vegas, you need to know Steve Cyr. He’s a casino host, a guy who makes sure you get free rooms, comped meals, private jet service, tickets to the Mayweather fight -- as long as you’re willing to gamble high enough to deserve it. The subject of Vegas tell-all Whale Hunt in the Desert and newly hired VP of player development at the freshly revamped Westgate Las Vegas Resort & Casino (formerly the Las Vegas Hilton), 51-year-old Cyr has a reputation for being one of the most aggressive hosts in town. He’ll press you to gamble beyond your comfort level and just might make sure you get the ritziest suite you’ve ever seen, complete with a fawning butler.

For our interview, Cyr reserved a 15,000sqft high-roller enclave at the Westgate, complete with more than a dozen TVs, hand-painted murals, and a private pool. It also happens to be the same room he once kicked Bill Gates out of. “Gates was renting it for $10,000 a night during the Consumer Electronics Show one year,” Cyr says. “He had it for Wednesday and Thursday and wanted to extend for two more nights. But I told him that he needed to get out of the room; Larry Flynt was coming, and he’d be risking a couple million dollars. Gates said that he would pay $15,000 a night. I told him that I would give him a credit line of $200,000, he could gamble it up, and keep the room for free. Bill Gates didn’t like that. Security came in and helped him pack. He left soon after. Rooms like these are for players, not tourists.”

As becomes immediately clear, Cyr -- who almost took a job running his father’s Howard Johnson’s in Salina, Kansas -- has no use for tourists.

There are 700 hosts in Las Vegas. Half of them hate me. They don’t like competition. They think I’m arrogant. They don’t think I should solicit other people’s players. My answer to that is, “You want Larry Flynt’s cell phone number? I’ll fucking give it to you. Good luck. Larry gets people calling him all the time.” I’m not afraid of losing him. I’ve sold my database before and made a ton of money. 

I don’t worry about people stealing my players because most hosts are lazy, and I’m not. I work hard. Hell, I got my first break after spending a year dumpster diving behind casinos, looking in the trash for discarded mailing lists of gamblers. I did it all over town, but got lucky at Caesars Palace where I found a Super Bowl mailing list. I had good telemarketing skills -- during college, I made money by selling vitamins over the phone and still get a boner when I put on my headset -- and cold-called every name on the list. They became my first group of players. At the same time, I was spending noon ‘til 7pm, every Friday, at McCarran Airport in Las Vegas. I’d hang out where the limo drivers waited to pick up guests who were flying in from out of town. Drivers stood there, holding placards with the players’ names and the casinos’ logos. I’d write all that down and then call the guys’ rooms. “I’m Steve Cyr from the Hilton. I met you when I was a host at Caesars. I told my boss you’re a big player and I am going to buy you a steak dinner tonight. Hey, what’s your date of birth, so I can set you up?”

With that information, I could get a report from Central Credit [which functions as the gambling world’s equivalent of TRW] and find out the guy’s credit rating. Then I would have him all set up before he even got here. I still go to the airport and do that. But now I know the limo drivers and bribe them with casino comps. If I see a driver from the Mansion [a super-luxurious hotel within the hotel at MGM Grand], I know he’s picking up a $100,000 to $250,000 player. And I’ve probably met the guy before, since nearly every casino in town has fired me. I call the guy and say, “This is Steve Cyr, I love the Mansion, but I just want to make sure they’re not fucking you over there.” Then I offer him a better deal than what the Mansion gives.

I used that approach to get a major Hollywood producer who we’ll call Mr. X. I had been phoning him for a year. Finally, he took my call and said that if I ever disturb him again, the next call I receive will be from his attorney. So I gave him the power line. I said, “I respect that. But I just want you to know you are getting fucked by the Wynn.” He said, “How am I getting fucked by the Wynn?” I said, “You just lost $2 million and you paid it because you’re a sucker.” He said, “How am I a sucker? If I had won, they would have paid me.” I said, “Yeah, but if your name was Suzuki or Yamaha, you would have paid only 1.8. You just ate $200,000 and you’re a businessman. I would give you a 15% discount [high-stakes gamblers often receive rebates on their losses].” He put me on hold and called his guy at the Wynn. The guy said that they give discounts, but only to international players. So, Mr. X put him on hold and asked when I could pick him up. I picked him up the next day and he won $1.6 million on his first trip. Lifetime, he’s lost more than $17 million with me.

I love losers, and I tell that to my players’ faces. I love the guy who just chases. Rookie hosts say they hope a guy wins on his first trip. Fuck that. I want the guy stuck before he checks in, after the limo drops him off. I want him to be chasing right from the start and trying to prove that he’s worthy. I want them to lose because I’m a house guy now [on salary working at the Westgate], and that will get me raises and bonuses. But, until very recently, I was freelance, and in Las Vegas I got paid on a theoretical basis [a percentage of what the gambler is expected to lose based on his average bet, regardless of how he does]. Back then I wanted my guys to win a lot and bet higher. I wanted them to win in Vegas and lose in Barona [a casino near San Diego where Cyr receives 10% of actual losses as a freelancer]. I got paid a maximum of $15,000 per player in Vegas. A guy won half a million, and I maxed out. So I said to him, “Fuck it. You’re a winner here. Let’s go to San Diego, where the weather is better.” Barona sent a plane. We helicoptered from the airport to the golf course. He lost 300 grand and I told him to go home with something. I’m not greedy. I made $45,000 that weekend from one guy.

On my best weekend, I made $314,000. I took a guy named Ben to Barona and watched him lose $1.5 million, which earned me 150 grand. It was late Saturday night, and he was supposed to fly home on a private plane the next day, so I left. Wednesday afternoon I got a call from my boss at Barona. He said he wanted to make sure I got the $150,000 wire. I did and I thanked him for it. He suggested that I check my bank account again and hung up on me. I looked and there was another wire for $164,000. I called back. He said, “Your boy missed his flight. He stayed and played and lost.” I took $100,000 of that money and put it in my daughter’s college fund. Now she’s going to University of Oregon. Thanks, Ben!

I’ve seen a lot of super-rich guys get broken. I’ve had had four guys commit suicide because they couldn’t stand being poor due to their gambling losses. One guy got himself murdered -- bludgeoned to death. From all of that, from seeing the emotional swings, I have learned that guys who talk about committing suicide don’t do it. I had a guy who owed money all around town. He told me that life is not worth living, he’s going to kill himself. I told him that he’s full of shit. Like I said before, guys who talk about it don’t do it. I told him he’s too much of a pussy. I was right. He never committed suicide.

Then there was a player, Ray, a big guy in the construction business. Every Wednesday for a year and a half, I would pick him up in San Diego at 8:30am, he went into his office for a few minutes, and we flew to Vegas. He gambled until 4 in the afternoon and then flew back to his office. Ray blew millions and helped make my career.

Then one day he came up to me and said, “I may lose my business. I’m going to quit gambling after this trip.” He mortgaged everything and needed to win $300,000 to complete a project. He was broke and owed about a million dollars all over Vegas. But Ray was good at my casino. His credit line was clear. We gave him 200 grand. That day he won over half a million in like two hours. He gave me a check for $400,000 and told me not to let him gamble with that money. At 2 in the morning we were in the bathroom, he was drunk, and demanding the check. My bosses told me keep him in the casino, and I told him he needs the money for business. He said, “Fuck you. Give me the money or I’m going to Caesars." I gave him the check. He lost it all, declared bankruptcy, his wife divorced him, he lost his business, his family stopped speaking to him. He still comes out to Vegas. But now he flies in on Southwest, brings two grand, and thinks he can make a run at it. He’s lost $11 million over the years.

Even worse, I had a player who met a hooker, we'll call her Kim, on his very first trip with me. She was so smoking hot, a friend of mine, and very savvy. She told him that she’s his good luck charm, that he didn’t have to pay her for sex, but that she wanted 10% of his winnings. He won $430,000 and gave her 43 grand. Next weekend it was the same thing. Six months later, he divorced his wife, married Kim, and she was pregnant. Ten years after that, he lost his last 70 grand at Red Rock. The guy was flat broke and he killed himself. I felt bad, but he had a great decade with Kim.

Next time you’re in a casino on a Friday night, observe the people coming in. For many of them, it’s the start of their weekend trip. They’re happy and expecting to win -- which I think is a little weird. In reality, two out of my guys’ 10 trips are perfect: they get comped, they have fun, they go home with five or six grand. The other eight trips, they get their asses kicked. They eat like birds and shit like moose. My average $50,000 player is happy to win 10 grand, but he usually loses 50.

Larry Flynt, though, is not average. When I met him, the first thing he said to me was, “Cyr, you’re my kind of asshole.” He is probably the one player I am afraid of. He is very rich and very disciplined. Most guys, if they win Friday night, they’re writing me a check on Sunday. Larry’s got his own jet. He’ll win on Friday night and fly himself home the next morning. Plus he’s a good negotiator. When I was getting paid 16% of theoretical, I split my commission with him. If he lost, he got a discount from the casino plus 8% from me. If he won, he got his winnings plus 8% from me. I’m close with Larry and that deal turned out to be the best business decision I’ve ever made. It gave me an edge over all the other reps. Now, with my full-time job, I can do the Larry deal at Barona and Atlantis [in the Bahamas], where I’m still freelancing, but not here in Las Vegas.

One-third of my gamblers are like Larry. They’re so rich they can lose a million dollars and not impact their lives. The second third are young, and as their age and wealth increase, their gambling increases right in step; my biggest guy at this moment, he started out as a $50,000 player and now $50,000 is his first bet. The final third should not be here. They’re the most fun but they should not be playing with me. They’re gambling above their means. They will be fucking broke at 50. For the first time, after 28 years in the business, I have more $100,000 players under the age of 40 than over the age of 40. I worry about them. They make money in some tech thing and think they can beat the game. Don’t forget, if you lose $100,000, you’re losing $100,000 that you paid taxes on. So you really lost $150,000 of what you earned. If you have $10 million, and you do that on a regular basis, you will go broke. Twenty-five years ago, my biggest players were all in their 50s or 60s or 70s. They might have been burning through their 401(k)s, but they had already lived life.

Whatever your situation, though, you should bounce around from casino to casino, rather than sticking with one host in one casino -- unless, of course, it’s me. Hosts know who plays where and competition makes them work harder for you. If a host at Bellagio hasn’t seen you in a while and he finds out that you recently played Wynn, he will over-comp. Loyalty is for airline programs, not casinos. And don’t be afraid to ask for stuff up front. Most people ask for airline compensation at the end. Ask for it first and you’ll get it whether you win or lose. Finally, use credit lines or wire money into the cage to get the best comps. We want to know what we can win -- and, truthfully, we often win it all. I can’t tell you how many guys wire in $100k and vow that they will lose only 40, that they’re doing it just to look good and get a better room. Last guy who wired in $100,000 to get the wraparound terrace swore that he would lose 30 or less. He dropped $96,000 and gave the last $4,000 to his wife for shopping.

But that’s not what I always want players to do. Generally, I’d rather see a guy blow 10 grand once a month than lose 100 grand in one shot and have a bad taste in his mouth because he dropped way more than he could afford. I’ve learned not to burn people out.

I’ll tell you a story from three months ago. I did something then that Steve Cyr in the 1990s would not have done: I was at the Cosmopolitan with a $5,000 player. In three years I do not remember this guy winning one time. Finally, due to blind luck, he won $43,000. His session ended, I walked him to the cage, and I made them give him a check for $40k. We agreed that I would take the check from him and FedEx it to his home. He was left with $3,000 in cash. I sent him to the Spearmint Rhino and told him to have a blast chasing tits and ass. That night, at 10:30, he called me, begging for credit so he could start gambling again. I turned him down. He told me he was going to go to Caesars. I put in his credit report that he is a slow payer -- which is a lie, but I knew it would stop anyone from giving him credit. He said I was a motherfucker and wanted nothing to do with me. Then, on Monday, his FedEx package arrived. He called me on my cell phone, and said, “Thanks.”

You hear this story and think I’m softening up? Fuck you. He now loves me for the rest of his life and I know he will never win again.

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Michael Kaplan is a journalist based in Brooklyn. He has written for Details, Wired, Playboy, and The New York Times Magazine, covers gambling for Cigar Aficionado, and is the author of four books. Follow him: @kaplanwords.