3men_Vegas

Three Guys Who Won Big (Or at Least, Big-ish) in Vegas

From a low-stakes room comp to a tax-dodging escape, here’s what can go down in the casinos of Sin City

Most people lose the cash they brought with them to Las Vegas… and then some more from several trips to the ATM. Everybody seems to know this — I mean, all those gigantic, opulent, air-conditioned palaces in the middle of the desert don’t pay for themselves, you know? But since most of us go there and lose, what’s it like to actually beat the odds, even a little? We did some investigating. Turned out, what happens in Vegas doesn’t always stay in Vegas.

The Comped Suite at Hooters

Jackson, 38: Two years ago, before a major sports tournament, my friend who’s a private pilot let me catch a ride in his jet to Vegas. That was a baller way to arrive! My friends were flying in the next day, so I had an evening mostly to myself.

The pilot friend and I went to Hooters casino because, although it’s kind of cliché, it’s a good time — atmosphere-wise it’s the cheapest casino there is, but it’s still fun. I started playing video poker — I like table games as well, but you can play the video machines at your own speed, whereas with table games, you’re playing at the speed of the dealer. If I feel like talking to people and being social, then I like the table games because it’s fun to interact with people around you — you run into some crazy characters in Vegas doing that! But other nights, when I just want to be by myself and in my own little world of gambling, slot machines are kind of fun. In my state, we have slot machines in every bar, and I’ve got kind of a reputation among my friends for winning at them.

In the course of about five hours there, I probably gambled $4,000, just going up and down on the same machine. But video machines have a points system based on how many times you actually spin it: The points are just based strictly on how many times you play, multiplied by how much you’re betting on that hand. So when you play for five hours, that’s a lot of money that goes coursing through the machine, even if your winnings aren’t that high. The players card they give you that you insert into the machine is keeping track of all this.

Eventually, a lady walks over and confirms my name. She says, “We’d like to talk to you about the points you’ve accumulated tonight,” and she gives me a free room — giant suite, top floor. Which, at Hooters, is… not awesome.

You’d think when you walked into a thousand-square-foot hotel room in Vegas you’d be blown away, like, “Oh, I can see forever.” But it wasn’t like that — there were probably four different, weird little rooms. The suite itself was 30 years out of date. It looked like a room the mafia would have been in decades ago and they hadn’t touched it at all. There were literally patched holes in the walls and the window had the film coming off of it, like when you try to do a tint job on your own car and it gets all bubbly. There was a place where there used to be a fridge — you could tell they just took it out and didn’t bother doing anything with it, so it left a big void in the kitchen. It was ghetto, but it was also funny. If my wife was there she’d have said, “This is disgusting! We’re not staying here.” But I couldn’t care less. I was alone — which is weird, being in a room that big by yourself — but it was still kind of fun.

Then they also gave me $300 in points that I could spend at the store so I literally bought my wife four different Hooters outfits: A waitress outfit, a football outfit, etc. (I don’t think she’s ever worn any of them.) I also bought my kids some gear — my wife was like, “Really? He’s gotta have a Hooters football?” The whole thing was just fun because it didn’t matter, and it was Hooters, and I didn’t care.

Blacked Out at the Blackjack Table

Tim, 50: I went to Vegas for a developer’s convention with several friends and a client. They invited me to a concert, but I said no, I’m playing, and went to the blackjack tables. I had $300 in my wallet, after an hour and a half, I was up $1,800. I remember there was a weird guy from Florida at the table — it was a fun and lively group. I was drinking Grey Goose and soda, splash of cranberry juice — the last thing I remember is my friends walking out of the concert and saying they wanted to go bar hopping, and again I said, “I wanna stay here and play.”

When I woke up the next morning, I was in my hotel bed. My head was sore, and I still had my shoes on. The first thing I did was call my friend. He’s like, “Where have you been? It’s Monday and we’ve got a meeting in 30 minutes!” I’m like, “Oh God, let me shower!” He said, “Relax, I’m just kidding — it’s Sunday, I’m down by the pool.” So I hung up the phone, and I’m wondering to myself, “What happened last night?” I look in my wallet and I have three $100 bills… and this pink slip. I unfold the pink slip, and all I can say is, “Oh my God. OH MY GOD.” I call my friend back and yell, “I’m in big trouble. Big trouble! I was spending a lot of money last night!”

I went straight down to the pool in my jeans and a sweatshirt — it’s 95 degrees out and I reek of alcohol. I showed my friend this slip and say, “I’m in huge trouble.” He starts reading it, then shouts, “Holy fucking shit!” over and over. People start to look. He says to me, “You won $26,000 — you have it in a casino bank account! How did you win this?” I said, “I have no idea!”

We went to the casino bank, where they greeted me by name when we walked up. They confirmed it, but still, I didn’t remember any of it. I called my friend who went to the concert, and he told me, “You wanted to stay and gamble, and right before we left you, the cocktail waitress handed you a drink. You said to us, ‘This is great — you don’t even have to ask for one, they just appear!’”

We all met in the casino and visited the table I was playing at. I start talking to one of the pit bosses, who said he was on duty last night. We’re like, “We just need to know what happened!” The guy goes, “By the time we got you up to your room, you were incoherent. But you had the nicest manners — you played quietly, nobody knew you were drunk until your head hit the table and you were out cold. At that point we took whatever money you had and we piled it up, took you to the elevator, you showed us to your room, and security put you to bed.” I said, “That’s so awesome! I’ve gotta start tipping everyone.” Then we asked him if we could see video footage, and he just laughed and shook his head.

That night my friends and I met with a client for dinner. I said to my friends, “Don’t tell the client anything about last night.” Our dinner tab was around $2,300 — I signed it to my room, and later that night I played three-card poker for the first time ever and won $5,000 more. When I checked out a couple days later, everything was comped, including dinner. I took my winnings as a check, then had to pay 41 percent of it in taxes. The rest I divided into two and started college funds for my two kids. To this day I really don’t remember anything from that night!

A Rental Car and a Suitcase Full of Cash

JC, 45: One winter awhile back, I broke my leg while skiing. For months I couldn’t do much. I was already playing blackjack a lot, but I never understood craps or roulette, so to fight off boredom I said to myself, “I might as well try to see if I can perfect this roulette thing.” I began studying all kinds of books written by former gamblers, degenerates, whatever.

In the process of studying the roulette wheel I figured out that casinos lay out their numbers differently — you have to really look closely at the wheel itself, which can change: 1 through 36 doesn’t necessarily have to be in order. A lot of people play favorite numbers, or numbers that are together on the table. If you ask, the casino will give you a card — they call it a cheat sheet — of that table. It’ll show you the way it’s laid out, and that’s how I started to study it. What I did was break it down into quarters of the wheel.

So after a year, I went to Vegas in crutches and a cast, thinking I’m gonna give this thing a shot. I flew in from California on a round-trip ticket and checked into New York-New York back when the casino was fairly new and it was really nice. When I checked in, they didn’t know my name — I’d never played there at all. I came to town with $6,000. I started to play blackjack and won a couple thousand, no big deal, playing $100 hands because I didn’t want to draw attention to myself. I was a little intimidated on how much I was gonna spend on roulette.

The following night I had the guts to go down to the roulette table and picked a table that I’d already studied. I sat down, ordered a gin on the rocks with lime, and started to play the numbers I’d programmed into my head to play. They were always the same numbers: I would play 15 numbers, $100 a number, and trust me, it gets very intimidating when you’re playing that much money and you’re not really a big whale. But numbers started to hit, and every time it started to hit, it’s 35 to 1 in the center, so it’s paying $3,500 — plus your hundred spot doesn’t get touched, so it’s $3,600 that’s on the table. I started to hit almost every single time, and my net profit is a little more than 50 percent, so that’s pretty good: I’m risking $1,500 to win $3,500, so I’m taking in $2,000 every spin. And within the first 20 minutes I started to gain control of the table.

When I hit 11 numbers four times in a row, I started to draw attention from the pit bosses, and little by little I’d start putting chips in my pocket. I wouldn’t trade for the big chips — I was making them play with black chips while I’d slip banana chips (the yellow, $1,000 chips) into my pocket. I was aware of everything that was going on around me, I just didn’t know how much money I was actually winning because I kept putting yellow chips into my pocket.

About the second hour in I started drawing a huge crowd — people who thought they were bringing me luck or whatever. Of course you also get your dose of professional women, hanging around like pigeons waiting for crumbs to fall. But even they couldn’t throw me off my game, not at all — when you get this adrenaline high, even though I was pretty buzzed, I wasn’t drunk enough to be obnoxious. The waitress, of course, was bringing more drinks and more drinks and more drinks. The casino wants you to be trashed so you’ll do stupid things. They want you to be distracted, and they want to delay you as much as possible. It didn’t work.

I played for four hours at the table. Not every spin was a win, so I had to compensate — I’d have a streak of two or three loses but then I started to play a couple heavy hands surrounding a number that I felt was lucky. As I was winding down my play, I knew that I was being watched really closely: The casino host introduced himself, asked where I was staying and immediately offered to upgrade me. It was all small talk, trying to get me distracted — they’ll do anything it takes to cool you off and break your concentration and delay the wheel. I was also tipping the crew that was spinning, and of course they’re happy that I’m winning. I’d tip them $100 for every big win, and over four hours that was a lot of money, so the bosses were keeping an eye on their people as well, not just me.

I left the casino floor and went straight to my room because I wanted to see how much money I had. I literally had no more room in my pockets. I had chips in my front pockets, back pockets, my coat — and they were chipping up as much as I’d let them. By the time I counted them all, I realized I’d won $170,000! I had no intention of winning $20,000 or even $10,000, it just sorta started to happen. As soon as I counted it, I could immediately feel that this was my last time playing in this casino. I felt it, because the pressure was on me.

I don’t think I slept much at all. In Vegas you don’t sleep much anyway, but with all these chips, I didn’t trust the safe in the room so I decided I’d use one of the casino’s safety deposit boxes. I kept some of the cash in there, hidden in a T-shirt, just so they wouldn’t see what I’m putting in there through the cameras. The whole time I was nervous as hell — I ate really well, and drank, but I couldn’t sleep, I was just too antsy. I wanted to get out of Vegas, and now I was worried about cashing in all those chips.

Once you cash in more than $9,000 in chips, the casino will automatically do what’s called a CTR, or a cash transaction report, to the government — you go into the system, and at the end of the year the taxman is going to come visit you. So I had to figure out a way to cash in all these chips, then figure out a way to get all that cash home, because there’s no way I’m taking that much cash on an airplane. It’s impossible!

So I made a plan. I had two days left, and I spent those two days cashing in chips, almost nonstop. I knew they were keeping an eye on me, so I’d go to a table, get out $500 in cash and get some chips, mix in some of my high chips, and go to the cage and cash them in. There’s nothing illegal about you going to the cage with $2,000, cashing it, and then 20 minutes later going back with another thousand because hey, you probably won. They don’t know. That keeps you in the gray zone.

I didn’t leave the resort for the next two days, and spent the majority of it in the casino. I wasn’t really out to have more fun — I’d already had enough. I had to get my cash and get out of there. I ate at Gallagher’s a couple times, the steakhouse there, and they comped my meals. I also ate at the hot dog place, Nathan’s. But I never walked outside — I wasn’t gonna leave my cash alone, and I wasn’t going to run the risk of getting my ass kicked outside of the casino. When you have pockets full of money and all you’re thinking is, “Man, I gotta get out of this place,” it kind of changes you.

At the end of the second day, when I cashed it all in, I didn’t have strapped, beautifully crisp bills — I had rubber bands, $20s, $50s, $100s. It was a disaster. When I finally cashed all out, I saw the casino host — he comped me the whole thing and said, “We don’t ever want you to pay for a room in Vegas again. We really like your playing, and we want you back.” At the time, I was too worried about getting home. I didn’t even show up for my flight — it was a couple hundred bucks or whatever, so who cares? But if I drove, I wondered, how safe is it having that much cash? If I got pulled over, I’d be done. But I rented a car one way, and drove straight back home nonstop, right under the speed limit. When I walked in my front door, I felt so glad to be home. I called my brother and said, “You’ve gotta help me — I keep counting all this cash, there’s so many bills I’m going nuts.” When he got to my house, he couldn’t believe it.

I bought a house with all that cash, putting 50 percent down. I sold it awhile ago for $590,000, so it ended on good terms. And I never heard from the IRS!

That was the last time I ever played roulette. I went back to New York-New York a couple times, and they comped me a penthouse suite and meals at Gallagher’s, and I threw huge parties, but it started to get a little bit tense because I knew that I was being watched left and right on the roulette and I didn’t want to get 86’d out of Vegas. Every casino at that time probably would’ve done that, and I didn’t want to lose my capability of going back to Vegas. To this day I go to Vegas and stay at upgraded places like Wynn or Encore, and get comped there. I like to play two-deck blackjack, which is hand dealt. I’m able to count it better and keep track of it better. But I never play roulette — I just don’t wanna get caught, so to speak. But maybe for the Super Bowl I might go hit up one of the higher-end, high-stakes casinos and play roulette again.