My interview with Dewey Tomko has been scheduled and rescheduled three times over the course of a Wednesday morning. He's in Las Vegas, officially, to play in the
Five-Diamond World Poker Classic at Bellagio (and he quickly manages to win $15,000 in a single-table satellite there), but for 60-year-old Tomko, business always extends beyond the table. In the old days, it would have been rounds of golf with six- or seven-figure amounts at stake. Today there's a TV deal that's closing for a show that will air on
ESPN (it centers around a series of gamblers' golf matches he's putting together for the sports network). And while the gregarious, bristly haired Tomko always has a lot going on, don't think of him as a poker dilettante. Though his profile is not as high as it once had been, he's played more consecutive
World Series of Poker main events than anyone in history, made 22 final tables, won three bracelets, and finished seventh in last year's prestigious H.O.R.S.E. tournament. Plus, if you happen to have a big bet you want to make, check him out. He just might give you some action.
Michael Kaplan: You used to be a kindergarten teacher, back in the 1970s. How does someone make the leap from teaching little kids to being one of the most notorious high-stakes gamblers in the world?
Dewey Tomko: I loved teaching and did it for six years, but that job cost me so much money it was ridiculous. I'd make $10,000 a night playing poker and $6,100 a year teaching. The final straw came after I lost about $30,000 playing golf on Memorial Day. The next morning, I was at the school, teaching phys ed. It was 10 a.m., and gnats were flying around my face. All I could think about was that the guys who had beat me out of $30,000 were out there playing golf again. I went into the school and told one of the supervisors, "Do whatever you have to do, get a substitute for a month and I'll pay him myself, but I quit." Then I went to the golf course and tried to win my money back.
MK: You and Doyle Brunson are old friends. Have the two of you gambled a lot at golf?
DT: Oh, yeah. One time, when I was in my late 20s, after I had stopped teaching, I managed to run my bankroll up to $98,000. It was a lot of money back then and enabled me to play in big games. Doyle called and wanted me to meet him in Nashville for a golf match. I agreed, but for two days prior, I had been playing poker without sleeping. I flew into Nashville from my home in Florida, got there in the morning, and told Doyle that I needed to check into the hotel and get some sleep. Well, I never even made it to the hotel room. I played him that day - despite being dead tired - lost the whole $98,000, and had to go back to Florida broke.
MK: Ouch. Have you done much sports betting?
DT: I used to be wild and crazy with sports. I remember once betting eight games for $100,000 each, losing all of them, and being down $880,000. I lost $500,000 a year playing fantasy football. Look at me at the poker table and you wouldn't imagine that I'd gamble like that. I'm tighter at poker. But with sports, where you lay 11-to-10, there's a lot of luck involved. And that's when the stupidity comes out. Everybody has an Achilles heel, and mine is professional football. I love it. I have to bet football.
MK: What's a typical Sunday like?
DT: I bet every game. (He hesitates for a beat, then reconsiders.) Well, not every game, but if a game is on TV, I have to bet it.
MK: With a smart opinion?
DT: No, with my opinion. And through the years, it ain't been so good. But I don't bet as high as I used to. These days, I bet $20,000 to $40,000 a game. When I'm out here, though, I bet more than I do at home. Money doesn't seem like anything. And when I get around people like Doyle, I have good intentions, but they bring out the devil in me. One year, we got together to watch the Super Bowl. Neither of us was going to bet the game. By the time the game was done, we were both broke. If there's one person who's got a worse opinion than me on sports, it's Doyle.
MK: I'm surprised that you don't partner up with a handicapper.
DT: I've had offers to do that, but I've avoided it. I'm kind of a weird guy. I would rather lose on my opinion than win on somebody else's. I bet sports because I enjoy it. But if I get to a point where I'm being financially hurt from it, I stop. I must've quit sports a thousand times in my life. But how are you not gonna do it? On a Sunday afternoon or a Monday night, every normal person in the world is sweating the game. If you don't bet it, it's like you didn't get invited to the party.
MK: In this big universe of gambling, where does poker fit in?
DT: For a long time, poker was my grind. I could always go back to poker. It was my life. During some times in my 20s and 30s, I played so much that if you asked me who the president of the United States was, I couldn't have told you. I played poker and slept. If somebody had died when the
World Series of Poker was going on, I wouldn't have gone to the funeral, whereas now, I can't even tell you who won the last
World Series of Poker.
MK: Maybe not, but you're still pretty damned focused when you play. Last year you won more than $400,000 in tournaments and didn't enter a whole lot of them. How do you contrast poker today with how it was back in the 1970s and early '80s?
DT: One big difference is that the guys in the game used to be such incredible characters. I'd play with them for eight hours and not say a word. I'd just listen to their stories. And it could get dangerous. We played with guys who brought guns to the table. I remember playing one night at the Nugget with the man who was Benny Binion's bodyguard. He was drunk, and when he was drunk, he was liable to take you out to the desert. I had $10,000 to my name, I was loser in this game, and bluffing. He showed his gun and said, "Kid, if you're bluffing me this hand, I'm gonna kill you."
MK: So what did you do?
DT: I bluffed him right to the river and had all of my money in the pot. He studied and studied and told me that I'd better not be bluffing, and that he wanted to see my cards. He folded jacks, and the first thing I did was muck my hand. I said, "You know I had a pair of aces, but I can't show you. It's against the rules." He didn't know how to answer that, and I raked in the money. But, man, I was sweating.
MK: You've made 22
World Series final tables and won three of them. When you look back at the ones you came close to winning - including finishing second to Carlos Mortensen in 2001 - do you have any regrets about how you played?
DT: There's not a thing in life that I regret or feel bad about. Everything I did in life either had a purpose or made me a better person or I learned from it. When Jack Straus beat me in the 1982
World Series championship, we both had the same amount of chips and he drew out on me. That was a great learning experience for me, and over the next couple of years, I went out and won a whole bunch of tournaments.
MK: What do you take away from a loss like the one against Straus or Mortensen?
DT: I get stronger, I get tougher, I learn to move on. I don't believe in second-guessing. Against Carlos, I played as well as I could play. Let me tell you something, Doyle won 10 World Series bracelets, and to get some of them, he had to outdraw the other guy. Look at when Chris Ferguson beat T.J. If Ferguson had come in second, nobody ever would have heard of the guy. Fate is fate. Everybody gets lucky at something.
MK: Speaking of luck, let's talk about proposition betting. I assume that you've made a few in your time.
DT: I've made millions of 'em. Once, I bet Jack Binion and Doyle $10,000 that I could swim from one end of a pool to the other without coming up for air. I'm telling you, buddy, when they pulled me out, I needed to be resuscitated. Just recently, I was playing golf with Phil Ivey. You ever see Phil Ivey play golf?
MK: He's not too good, right?
DT: He's so uncoordinated that I figured he wouldn't be able to shoot a basket. Now, I once made 15 out of 15 in Lake Tahoe to win $65,000, so I thought I was pretty good. Well, when Phil and I came off the course, he said, "I'll shoot you some basketball." We went to the clubhouse, where there was a basketball court, and I said, "We'll shoot 3-pointers; first to hit one gets $20,000." I figured I'd be robbing him. Well, I'm 60 years old, and that trip to Tahoe was a long time ago. You think I thought about that? I shot first and didn't even hit the rim. I was so embarrassed. Then, he stepped up to the 3-point line, and you know what he did? He swished it. Phil Ivey can definitely shoot baskets.
MK: When you do these prop bets, to what degree are you making them simply to generate action?
DT: That's part of it. But they're also just foolish bets. I'm leasing out my casino [the Horseshoe in Costa Rica] and bet the lessee $100,000 to $20,000 that he will make $1 million during one of his first two months. In this particular case, I can win only $20,000, but I can lose $100,000.
MK: Sounds like a good bet for the guy who's leasing your casino.
DT: It is. But I opened my mouth, which is when I get in trouble. Like all gamblers, I'm opinionated, and once I open my mouth, I need to back up what I say.
MK: Yeah. But I'm guessing, in the long run, you've made more money than you've lost as a result of goofy bets.
DT: A perfect example is the time I flipped a guy for $50,000. How many people are gonna be willing to do that?
MK: Wait a minute. You flipped a coin with somebody for $50,000?
DT: That's right. This guy and I were arguing about how to match up at golf. He was being hard, and I told him, "Listen, I'm not trying to take advantage of you; we're only trying to play for $50,000. If you think we're even, fine, let's flip a coin. Then we don't have to go out there." I didn't think he'd agree to do it, but he said OK. We flipped and I lost.
MK: You paid this guy $50,000 on a coin toss?
DT: Naturally.
MK: Did it bug you?
DT: No. That's just part of gambling, and it wound up making me a lot of money. The guy realized I would gamble, and in golf, that's a big part of making money.
MK: The other part is convincing someone that you're giving him a good game.
DT: You can never beat anybody out of a lot of money if he thinks he's got the worst of it. But if he's got it in his mind that he's got the best of it, and he loses, he'll figure that he choked or you got lucky, and he will keep playing and playing and playing. If you shoot 75 and the other guy shoots 80, you give him two shots a side and need to figure out a way to win. He's got the best of it, but you win by out-grinding him, pressing bets, playing higher, playing a little better, making him choke. That's how you win money. The successful gambler has mental toughness; he concentrates under extreme circumstances and extreme pressure better than the other person. I can't focus on the first three holes, but when everything is on the line, I play my best.
MK: Beyond gambling, you're involved in a whole bunch of businesses. I find that interesting in light of the fact that many people play poker specifically to avoid the structured life of a businessman.
DT: That's right. But did you ever see a guy who marries at 17, gets older, and wants to do nothing but party? I'm the opposite. When I was young, poker was everything to me. As a result, I missed the challenge of being a businessman, and I'm the kind of person who always needs a challenge. I can't sit on the porch.
MK: What makes business so challenging for you?
DT: That I'm so bad at it. For example, Doyle, Chip [Reese], and I lost $7 million on a TV station. I can name you 50 things I got involved with and wound up with zero. Know what zero means? It means that I put in $5 million and ended up with zero. We looked for the Titanic and lost money on that. We had gold mines in El Paso. I did everything you can imagine. But that's when I was playing poker and out for a fast bet. A guy told me to give him $171,000 and we could look for gold off the coast of Venezuela. It was always high-stakes stuff. When somebody came to me with something reasonable, like buying land, I'd ask him if he was crazy. It was too slow for me. But now I own a golf course, I own a casino with a sportsbook and cardroom inside, I own orange groves, and I own Vines Grille and Wine Bar in Orlando. Anything that interests me, I go out and do it. If I was into fishing, I'd own a lake.
MK: Where does most of your money come from these days?
DT: Orange groves. When I was young, I bought a lot of orange groves. I had a 15-year mortgage and it was a good tax write-off. Today I own them all, and these orange groves that I thought were nowhere are now worth $50,000 to $100,000 an acre. They're never going to go down in value, I get fruit off them, and I sell the fruit for $2 million or $3 million a year. These orchards are paid for and they've gone up like crazy. It was dumb luck.
MK: As a guy who's done a lot of gambling and owned a casino, do you find it better to be the player or the house?
DT: What do you think? Every time someone walks in, he's got the worst of it.
MK: What's more fun?
DT: Playing. Owning a casino is a way to make money. You're way happier when you win as a gambler.
