Playing in Ivey's League

Phil Ivey, one of the world’s best poker players, has parlayed his card skills into a high-end, jet-setter’s lifestyle.
| By Michael Kaplan | From Phil Ivey, March/April 2010

On the evening of November 8, 2009, less than 24-hours after busting out of the World Series of Poker main event final table, Phil Ivey indulges in one of his favorite pursuits: Running rough-shod over a Bellagio craps game. Ivey is casually dressed, in knee-length shorts and pristine Nikes, looking as if he just strolled in from a round at Shadow Creek. Spread out in front of him is a strip of $5,000, $10,000, and $25,000 chips. Surrounded by friends and relatives who came to town with hopes of witnessing Ivey winning his first WSOP main event, he watches the bones roll and sprays thousands across the felt.

Save for a mild dustup over some kind of technical issue-to settle it, Ivey calmly suggests a call to his friend and MGM Mirage executive Bobby Baldwin-the poker pro appears to be in heaven. No doubt, this is helped along by the fact that when he lofts the dice-his style is to throw them high and slow, as if he's pitching a pair of softballs- they seem to land in his favor. As the session ends, I overhear Ivey casually stating that he made a big score.

Then he heads off to his suite to shower and change clothing. An hour or so later, he reappears and takes his gang of 20 to the Bellagio's Jasmine for a comped Chinese banquet. Word circulates that Ivey has a private jet on standby tonight and that he might spontaneously take off for points unknown. Or else he's going to the Bank, where a table and bottle-service await him.

He does the latter, making it clear that finishing seventh in the World Series hasn't exactly left him lost in considerations over what might have been if he had played at least one hand differently. Ivey folded pocket Jacks to a reraise from poker neophyte Antoine Saout, which probably surprised a lot of fans who watched the WSOP play out on television.

Later on, Ivey tells me that the hand had more dimensions to it than the viewers at home could recognize. "I was in a shove or fold situation when Antoine [who had two 7s] reraised me," says Ivey. "He hadn't reraised me once during the entire tournament. I thought he was playing pretty solid. It turned out to be an abnormal raise, but I didn't want to risk my whole tournament with that play. Darvin Moon was to my right, and I felt he would make some mistakes. I ultimately got all my money in with Ace, King against Ace, Queen and lost." He shrugs, indicating that there was nothing else he could have done. Then Ivey acknowledges, "It's a shame I didn't do better. I had reads on everyone at the table."

Whatever the case, Phil Ivey has no cause for second-guessing. Widely recognized as the most gifted poker star on earth, he's also the best-known and most respected player in the game. Transcending the world of poker, Ivey hangs out with the likes of Jay-Z, Sean "Diddy" Combs and Michael Phelps. His lifestyle is as high-tone as that of any celebrity or sports star. Via televised tournaments, programs such as "Poker After Dark," and commercials promoting the online poker site FullTiltPoker.com (of which Ivey is a well-compensated founding representative), Ivey gets enough TV exposure that strangers stop him for autographs. Nevertheless, he wears his prominence as casually as other players wear their logoed baseball caps. "I've never been too interested in fame; I didn't see the point and I figured that I might as well stay under the radar," says Ivey, leaving the impression that he has since come to understand the value of a decent Q Rating. "Even now, though, I'm not really famous. I'm just a poker player and pretty comfortable."

Whether it's by design or accident, Ivey stokes the public's fascination by maintaining a quiet mystique that the more vociferous Phil Hellmuths and Mike Matusows of the world can't come close to touching. And Ivey backs it up like nobody else. His skills as an online player are uncontestable-according to HighStakesDB.com, Ivey won more than $6.5 million playing online in 2009-he happily antes up in the biggest cash games available, and, even though he usually buys into only the richest tournaments, Ivey recently emerged as the winningest player in that arena (with seven WSOP bracelets and more than $12.6 million in proceeds-not counting what he's made through various side bets, which routinely wind up in the six figures). Also, he manages the business of poker very well. At one point, for example, Ivey was backing most of the action in a highly profitable seven card stud game that gets built around Larry Flynt.

He's quick to point out, though, that none of this is as easy as it looks. For example, during the World Series main event most players went to sleep after each grueling day of the tournament. Ivey, on the other hand, got driven from the Rio to the Bellagio and profitably played the Big Game ‘til dawn, managed a couple hours of sleep, and returned to the Rio for the next day's session. "People think I just show up and win money," he says, adding that the nights without sleep were financially worthwhile. "But that's not the way it goes. After playing, I spend hours thinking about hands and decisions, what my opponents thought, what I thought, what they did when they bet . . . I work hard for my lifestyle."

Six weeks after Ivey's WSOP bust-out, I am back in Vegas, chatting on the phone with Ivey's driver, Akida. He tells me to come down from my room at the Palms and meet him in valet parking. Ivey's just flown back from a holiday trip with his extended family in Miami. He wants to meet with me. I climb into the front seat of Ivey's black Range Rover, with gray shaded windows, and Akida heads down Flamingo Road to the side entrance of Bellagio.

Inside, I catch up with a fast-stepping Ivey at the casino cage. Today he's dressed in a beautiful, pinstriped, bespoke suit. He cashes out a fistful of high-denomination chips and chats on alternating cell phones. Akida and I follow Ivey back to the car. Ivey chain calls and answers, finally getting into a conversation about the comps and rebates he'll be receiving at the newly opened Aria Resort & Casino at CityCenter. Akida wends through a complex series of turns that take us to a private entrance, specifically for guests who are staying in Aria's most luxe suites. Ivey clearly plans to get the most out of his gambling-never mind that casinos carefully calibrate their games to put players at a disadvantage.

On the way in, Ivey tells me that he is fresh from a baccarat spree at the Venetian, where he lucked out and managed to hit seven bankers in a row. He refuses to tell me how much he won, but I feel comfortable in assuming that Ivey played as high as the casino will permit. Considering the stratospheric level of his gambling, it would be easy to view Ivey's non-poker play as reckless. But there are some in the poker world who believe that Ivey is too smart to gamble in the pit without some kind of an edge. Ivey himself points out that going against the house fosters a wild image that can be leveraged in poker. Jeff Fried, the attorney and entrepreneur who serves as Ivey's advisor and business partner, puts a sharper point on it: "I don't think the dollar level is recreational and I think this is part and parcel with the Phil Ivey gambling enterprise. This is Phil's business, even playing a game that most people view as recreational. [Playing craps] is him going to work."

Ivey leads us inside the hotel and we proceed toward a VIP check-in desk. An attractive, well-built female casino host greets Ivey with a smile. Akida makes eye contact with the host and he politely says, "I don't know you very well, but I wonder if you would marry me."

The host laughs. Akida good-naturedly says, "I'll take that as a no."

Smiling crookedly, now holding a key card, Ivey looks up and comments, "Of course she will. Of course she'll marry you."

Obviously, he's joking. But he's joking in the tone of a gambler who's accustomed to having every need catered to by casino emissaries.

The life of Ivey far exceeds that of a typical superstar poker player-in terms of everything. He plays higher, travels better, and spends bigger than anyone in the game. His standards resemble those of a big-time CEO, and his demands are right in line. "Phil can't wait for anything, and he's got no room in his wallet for bills smaller than $100," says Barry Greenstein, a high-stakes poker pro and a longtime booster of Ivey's. "I think of myself as a good tipper, but Phil dwarfs me. Travel anywhere with Phil and you always know that he is going to be in the nicest suite at the hotel."

This much is made clear as we head up to his digs at Aria. No standard hideaway, it's the kind of accommodation that exists primarily as a posh holding tank, inside of which casino personnel can curry favor with their most prized whales. The windows are floor to ceiling; the furnishings are sleek and modern. An exposed staircase rises to a second floor of bedrooms, though you can also get up there via private elevator.

When greeted by a pair of glad-handing male hosts, dressed in MGM's standard-issue suits and ties, Ivey half-kinddingly gripes about the lack of a private pool. The hosts manage to assuage his complaints with a couple bottles of 1989 Vega-Sicilia Unico (a Spanish red wine that can go for up to $1,000 in restaurants) and a Ziplock bag containing five exquisite cigars. Ivey sails one below his nose, smells it, savors it, clips it, and lights it up. The hosts uncork a bottle and help themselves to glasses of Ivey's spoils.

From the tips of his crocodile skin Gucci loafers to the top of his perfectly barbered hair (cut and styled every few days at Salon Bellagio), the 33-year-old, recently divorced Phil Ivey really is a picture of elegance, success, and discernment. Taking off his suit jacket, untucking his white shirt, stretching out and relaxing, he acknowledges that his taste level emerged strangely. "It's all about the lifestyle," he says. "You play craps for obscene amounts of money and all this great stuff is complimentary-food, wine, clothing, jewelry, airfare. I'd be at dinner in one of the Bellagio's nice restaurants, looking at a wine list, and I'd say, ‘Grace Family wine? What is that?' I'm told it's a very good bottle and I see it sells for $2,500. So I say, ‘Great. I'll order it.' Same with Screaming Eagle. Then I ask questions and learn about wine. I get exposed to high quality wines and food and cigars and clothing, and I figure out what I like. Lately, I've been getting into this Spanish red."

Cigars came to Ivey under similar circumstances. "Those started after I began golfing," he says. "I got into golf as a way to have something to do outside of gambling. But as soon as I started playing, everyone was lined up on the driving range, wanting to gamble with me. Doyle [Brunson] hopped out of his wheelchair just to have a shot at me. I wound up gambling a lot at golf and became good enough that I don't have to chase my ball all over the place. While playing, I got introduced to cigars. I'd see people on the course, smoking cigars. I figured I would try them. I started out with Macanudos and thought they weren't too bad. I've since worked my way up. I have a humidor full of cigars. But my favorites are the Partagas Salomon II Especialidads."

Just as Ivey's taste for the good life has gotten fancy, so have his options for making money. Five or so years ago, while playing craps at Bellagio, Ivey happened to meet Chris "Gotti" Lorenzo, a well-known hip-hop hitmaker who's worked with performers such as Ashanti, Ja Rule, and DMX. Lorenzo became Ivey's friend and then his manager. Hoping to help Ivey break out beyond poker, he brought opportunities that included six-figure sneaker and apparel deals (one with Reebok). Ivey turned them down. Then there was an opportunity for a documentary on ESPN. Ivey rejected that one as well. "My plan is for Phil to not have to play poker for a living," says Lorenzo, who along with Fried, is a member of Ivey's inner circle, enjoying a relationship that goes beyond business. "Right from the start, I told him that I won't let him get Stu Ungared, dying broke or in debt. I'm hoping to get Phil into a position where he can play poker because he wants to. Not because he has to."

This past January, collaborating with Jeff Fried and Chris Lorenzo, Ivey received an enticing opportunity: to be the face of Mexico's newly launched lottery, which can be played on mobile devices and promises to be extremely lucrative. Fried expects Ivey's involvement (as an investor, an endorser, and a consultant) to generate nearly $10 million over three years. Ivey went for it, knowing that if all goes well, it can mark the beginning of his emergence as poker's first Madison Avenue-friendly practitioner.

Through Fried, Ivey has also gotten involved in real estate investments and hosted the 2009 Congressional Award charity poker tournament. Fried, who's mixed it up with his share of celebrity athletes, finds himself impressed by how confidently and fluidly Ivey moves through the worlds of politics and business. "Phil Ivey jets into Washington from Europe to host the tournament; he draws all these senators and congressmen, and, in turn, they draw corporate support for the charity," explains Fried. "The next day Phil is in the Oval Office with Chris and I. The president had just left, we missed him by an hour-and-a-half, and somebody wants to show us the First Lady's office. We walk in there and she has a beautiful china bowl with apples in it. Phil reaches down for one of the apples. I say to Phil, ‘I'm not sure we're supposed to be eating them.' Phil takes a bite and replies, ‘So what are they there for?' That shows you how comfortable Phil is. I wouldn't have eaten the apple."

As far as Ivey himself is concerned, he likes to blue-sky about opening an eponymous steakhouse and launching a line of premium cigars. Chris Lorenzo says that Ivey has ambitions to own a casino that caters to the highest of high rollers. However, when it comes to something concrete for the immediate future, Ivey seems most excited about a possibility of giving up poker for a while and taking a shot at the biggest casino in the world. "I'm thinking of trying day-trading in New York," he says. "I have a friend who does very well at it. I want him to help me become the first really successful poker player who goes in that direction. He's willing to stake me, which will be a first for me. But I don't know anything about day-trading and if he's up for teaching me, and betting on me, then, sure, why not?"

I suggest that maybe Ivey can get some tips from Erik Seidel, a fellow founding representative of FullTilt, who preceded his poker career with a successful stint trading options. "Erik is a little more conservative than me," Ivey says dismissively. "I don't know that investors would want me managing their money. If I do, they might end up with a lot or they might end up with zero."

Despite Ivey's easy propensity for commuting relatively short distances by helicopter-when he landed on a field near Wembley Stadium, to attend a Coldplay concert, during a day off at the World Series of Poker Europe, he was mobbed by British kids who mistook him for Jay-Z-shooting dice in exclusive gaming rooms, and zipping around in private jets, his current life is a world away from the one he was born into. In fact, his original attraction to poker grew from a lack of air conditioning. His grandfather, who lived downstairs from the Iveys in the working-class town of Roselle, New Jersey, happened to have air conditioning and a penchant for poker. Initially, young Phil went down there to cool off. A short time later, though, he descended the steps primarily for penny-ante card games that he played with his granddad.

By age 16, Ivey had graduated beyond pennies. He got himself bit by the gambling bug and made his first trip to Atlantic City. "I walked through the door of the Showboat and chills went up my spine," he remembers. "I played blackjack and lost $70. But I still loved it. I started taking the bus down and gambled with the money that I earned working at McDonald's. At first I just played poker to kill time. I wasn't concerned about making a profit. I just had fun."

While other kids focused on finishing high school and selecting colleges, Ivey fixated on seven-card stud. He worked his way up through the A.C. poker stakes and moved into an apartment there after finishing high school. Not yet old enough to gamble legally, Ivey had a fake ID that listed his first name as Jerome. He spent so much time in the Taj Mahal card room-playing for 16 hours a day, repairing to the apartment for a quick night's sleep, and showing up again the next morning-that other players there began calling him No Home Jerome. It didn't bother Ivey. He remembers his early years in Atlantic City as a blissful time. When he felt comfortable in the $75/$150 game, Ivey knew he'd be able to make a go of poker as a career. Erik Seidel once described him as "a guy who plays poker as if the game may end tomorrow."

In time, Ivey got good enough that he felt himself outgrowing the confines of Atlantic City. He started making forays to Vegas and settled in for extended residencies at the Commerce Casino in Southern California. Eventually that led him to Larry Flynt's stud game, where the limits were 20 times higher than what Ivey was accustomed to playing. Remembering that success at Flynt's eluded him for seven months-and required frequent dips down into smaller stakes games to replenish his bankroll-Ivey says, "When you move up in levels, it just becomes totally different. Players read hands better and they know what you have. You need to adjust."

Despite the fact that Ivey was losing, Barry Greenstein, who, at the time, derived much of his income from the Flynt game, remembers being impressed by Ivey's ability to learn and the manner in which he handled his financial beats: "Phil took it like a man. He wasn't a complainer. And, clearly, he was a thinker." However, after seven months of losing money, Ivey vowed to Greenstein that if he didn't win on a particular night, he'd take a break from playing in the so-called Larry Game. "That night catapulted Phil into having a decent bankroll. It saved him a lot of time."

Meanwhile, Ivey was making noise in Las Vegas as well. During 2000, he won his first World Series of Poker bracelet by outplaying Amarillo Slim heads up in the $2,500 pot limit Omaha event. Slim, at the time, was known for being extremely tough in the final stage of a tournament. He had a knack for endlessly chatting, putting people off their games, and extracting information that players would be best off not releasing. Despite a four-to-one chip deficit against Slim, Ivey carved up the veteran pro in less than an hour. At a post-game conference, he offered little more than a three-word sound bite-"It feels good"-before walking off with his bracelet, quite possibly in search of a good cash game.

Ivey's out-of-nowhere upset may have surprised casual observers, but the poker cognoscenti were already on to him. "Phil has a higher pain tolerance than anyone in poker," says Howard Lederer who claims to have been the first poker pro to recognize Ivey's potential. "When you play a high-stakes poker game, you always need to make the right decision, but in the back of your mind you sometimes wonder how much you will hate losing a quarter-of-a-million dollars if that right decision is a bluff that may not work out. Sometimes you'll catch Phil trying to pull off those kinds of plays. But then you see that the loss doesn't hurt him, and it's scary. You recognize that you can't get Phil to back off."

Greenstein recalls the precise moment when he saw Ivey grow into being the player that he is today. Among the top pros he now went up against, Ivey became known for playing more aggressively than would seem optimal. But then, during a session at the Bellagio in 2004, Ivey began capitalizing on his reputation. "I distinctly remember one day when other players did not give Phil enough credit," says Greenstein. "That day, after the game, I said to Phil, ‘These people are in trouble.' They will pay off when he is there with a hand, and then, if they tighten up, he will run them over. I saw Phil go to that next level, and it was definitely a landmark day in his career."

More recently, the successful online pro Phil Galfond had a firsthand run-in with Ivey's ability to quickly adapt and change it up. They were playing $300/$600 no-limit hold'em on FullTilt and Galfond sensed that Ivey was check-raising too frequently, thus inducing Galfond to fold potentially winning hands. He viewed the gambit as a mistake and began reraising Ivey's check-raises. "What I underestimated," Galfond told me, "is how quickly Phil adjusts." By the time Galfond began taking advantage of Ivey's so-called mistake, Ivey had already tightened his game, and, in turn, took money from Galfond on the other end of the play.

This anecdote illustrates the kind of razor sharp, resilient mind that has allowed Ivey to beat the best poker players in the world. His stakes have risen to the so-called nosebleed levels and so have the rewards that come with success. Ivey currently owns two Rolls Royce Phantoms and a $500,000 Mclaren. He's seen the world and golfed on its finest courses. Ivey splashes around money as if life is a giant poker game in which everything has a price, whether it's to get extra-personalized service from a hotel butler, convince a teetotaler to take two shots of tequila (that endeavor ran $10,000), or bribe a chef to open a closed steakhouse as he did in Montreal.

Chris Lorenzo remembers the aftermath of a massive sushi and sake spree at the Bellagio: "Phil had $12,000 in his hands and told the waiter to take his tip. This waiter didn't know what to do and called over the manager. Phil held out his palms full of $100 bills. Finally the waiter dipped in and took like $6,000. As we were exiting, Phil joked, ‘Man, that guy has big hands.' "

Nolan Dalla, the media director of the World Series of Poker, remembers playing a round of golf with Ivey and a couple of other guys at the elite Shadow Creek-which Ivey treats so casually that it might as well be his favorite county course-and somebody in the foursome mentioned that his caddy happened to be the son of a well-regarded Nevada senator. Dalla acted like it was a big deal. Ivey deadpanned, "If the senator was your caddy, then I'd be impressed."

As when he responded to his driver's marriage proposal at the front desk of Aria, Ivey was joking on the golf course. But, on some level, he also wasn't joking. As I've been told by people close to Ivey, it takes a lot to impress him.

Back inside Phil Ivey's suite, wine is flowing. Cigars are being smoked down and Ivey comments that they get better as you go deeper. He's right about that. A businessman friend of his has just popped by, lunch gets ordered, and the two hosts scramble to see if they can score Ivey a couple of seats in a private box for tonight's Black Eyed Peas concert at Mandalay Bay. Ivey's got his driver making arrangements for the private jet that will fly him to Cabo San Lucas for a quick get-away that precedes a string of upcoming tournaments.

In Ivey's world, a heady mix of hard-core gambling, highly calculated poker play, and sybaritic luxuries all meld together and feed off of one another. Thanks to online poker, he can buy into massive games from anywhere in the world and thanks to the largess of casino comps, he can often fly there gratis. So Ivey moves with the wind and has attained a position in life where he only does what he feels like doing. It affords him the air of a cool cat and a free spirit-albeit one who's under a self-imposed gun to keep betting money and continue winning it. To do anything else, seemingly, would go against Ivey's very nature. Almost built into his DNA is an understanding of odds and opportunities and a bottomless desire to continually exploit them.

At the core of it all, though, is Ivey's love of action. He's been out of it for the last few hours, and gambling seems to be on his mind-especially with a casino right downstairs. Ivey talks about wanting to play a little craps. But an impending commitment promises to keep him away from the tables. He gets into a conversation about the security of his suite and potential for the floor-to-ceiling window to be broken, perhaps by a despondent gambler looking to leap.

While others in the room consider the possibility, Ivey reverts to form and tries to create his own action. He looks at the businessman and says, "I'll give you a $50,000 free-roll if you can punch your fist through the glass."

The businessman seems far from game to accept the wager, but there's little doubt that if Ivey really wants to see it happen, he'll happily raise the stakes.

Michael Kaplan is a Cigar Aficionado contributing editor.

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