House of cards

Barry Greenstein plays poker with cold calculation, and has won more money at the tables during the last five years than anyone alive, financing an extraordinary lifestyle.
By Michael Kaplan and Brad Reagan / Los Angeles Times

In the twilight of a flawless Friday afternoon on the Palos Verdes Peninsula, just before the start of last Labor Day weekend, a secluded beach cove slowly filled with jet-skiers and surfers. On the shore, removed from the crashing waves, two teenagers settled in for a romantic picnic while, farther down, a young dad taught his son the rudiments of building a sand castle. In an 11,500-square-foot pink stucco behemoth of a house perched on the cliff above, Barry Greenstein had just rolled out of bed. The 49-year-old peered down at the pleasure-seekers and contemplated his plan for the coming days: try to win more than $1 million in cash at the poker tables—"a nice thing to be able to do," he says.

Greenstein slipped a pair of silver slacks and a canary-yellow button-down over his 5-foot-8, 150-pound frame, ran a comb through his bristly black hair, and ignored the perpetual five o'clock shadow that covered his long and narrow face. He strolled to the kitchen in the other wing of the house, where his girlfriend, Alexandra Vuong, handed him an energy drink, told him where to find his favorite Gucci belt—the one with a gold G buckle that his kids teased actually stood for Greenstein—then pushed him out the door with a kiss. Save for the unusual hour of departure, Greenstein acted like any other successful businessman preparing for his daily commute—and that's not exactly an accident.

To Greenstein, poker is purely a business. He is one of the world's wealthiest, shrewdest and most fearsome card sharks, but all things being equal, he'd rather return to his old job as a computer programmer or maybe pursue his dream of becoming a math professor. All things are not equal, of course, and math professors don't live in mansions overlooking the Pacific Ocean. "There are a lot of people who feel that they would play poker regardless of how they do, because they love cards," he says. "The reason I play is strictly to make money."

In the first five years of this poker-crazy new millennium, Greenstein earned more money playing the game than anyone alive—by some estimates in excess of $20 million, a figure he does not dispute. His prosperity is on copious display in his massive home, which overlooks not only the ocean but also a seaside golf course being built by Donald Trump. Greenstein recently added an indoor pool, and his girlfriend is planning to remodel their immense kitchen. The one blight in all of this domestic luxury is an interrupted view from one of his balconies. It ought to look down upon the adjacent course's clubhouse; instead, it offers a view of his neighbor's Spanish-style roof.

Until four years ago, that property was vacant and Greenstein planned on purchasing it to preserve his vista. But then he lost $1.5 million in a monthlong game of Chinese poker with high-stakes gambler Ted Forrest and fell into a brief cash crunch. That allowed another buyer to swoop in and snatch the property out from under him. The neighboring house, he says, "is a reminder not to do foolish things."

As he steered his silver Jaguar out of a private cul-de-sac and toward the night's game, Greenstein confronted a glut of voicemail messages on his cellphone. Because he has been on such a tear, he is a sought-after commodity for the TV producers and reporters who feed the public fascination with the game's stars. "Poker has just gotten too huge," Greenstein muttered under his breath.

On his better days, he admits that he doesn't really mind the attention as long as it adds to the game's growing popularity. Because, ultimately, that boosts his bottom line. "There are a lot of wealthy people who have not been able to play poker because of the stigma associated with it," he says. "But it is becoming more socially acceptable. That means you are going to have more of those people dumping money to people like me."

Alternately dialing and talking, Greenstein maneuvered the sports car through the hills that buffer his swanky community from the L.A. smog and made his way toward downtrodden Gardena. There he reached the incongruous Art Deco facade of the Hustler Casino, owned by porn magnate Larry Flynt. He zipped into the parking lot and over to a private parking space near the entrance. A security guard greeted him at the front door: "Good evening, Mr. Greenstein."

Greenstein nodded and strode confidently into the casino. Ever since 1987, when the state Supreme Court ruled that poker was a game of skill—and not a form of gambling—California has boasted a handful of reputable, no-frills card rooms, most notably the Bicycle Casino in Bell Gardens and the Commerce Casino in Commerce. But Flynt raised the bar in 2000 when he opened his $40-million venture. The décor is less tawdry than you might expect from the man who built his fortune on Hustler magazine, but the maroon-velvet walls and deep-red-and-black checkerboard carpet still exude the vibe of an upscale brothel.

In a quiet back-left corner of the main room, beneath a gaudy chandelier that makes the ceiling seem as if it'sleaking costume jewelry, Greenstein joined poker pros Phil Ivey, Johnny "World" Hennigan and Danny Robison, who were all waiting for Flynt to arrive. Flynt, after all, was the draw—not only because he owns the casino but, more significantly, because he doesn't mind dropping several hundred thousand, or more, in a few hours of poker. He is a serious player, and a good one, but he's smart enough to know that the pros compete to get their hands inside his deep pockets.

"I've been supporting these guys and their families for five years," Flynt says. "I like to play with the best. Otherwise what fun is it?"

It was hardly a put-down to be the weakest player in this lineup. Ivey, the lanky 27-year-old out of Atlantic City, N.J., is considered one of the game's top young professionals. Robison had been among the premier Seven-Card Stud specialists in Las Vegas for more than 10 years until he was derailed by a cocaine addiction in the 1980s. Now born-again, he splits his time between running a Bible study for poker players—God's Winner's Circle, he calls it—and playing high-stakes poker himself. Hennigan is a hard-charging natural gambler and an unabashed sinner. His self-destructive tendencies include a propensity to drink at the table, but they're more than matched by his talent. On this night, Hennigan was drinking coffee.

As Robison sat quietly and Hennigan monitored a notepad with a long list of his sports bets for the day, a poker-room manager brought Greenstein a tray stacked with maroon-and-pink $5,000 chips and yellow-and-blue $500 chips. A dealer divvied out 13 cards to him and an equal amount to Ivey, Greenstein's good friend and frequent gambling companion. Two of the most successful players in the game—and arguably the most dominant pros of 2004—they are too restless to be out of action for very long, so they regularly occupy their downtime by playing Chinese poker for $2,000 per point (serious stakes that quickly and routinely end up with six figures flowing one way or the other). Yet, because it's a fairly mindless form of poker in which luck generally trumps skill, watching Ivey and Greenstein screw around at this is akin to witnessing Tiger Woods and Phil Mickelson playing a million-dollar round of miniature golf.

In the course of the next hour, Greenstein took Ivey for close to $200,000—all before the real action started.

Although other men of his financial stature might hire expensive interior decorators for their homes, Greenstein made most of the design choices for his palatial digs himself, drawing inspiration from the Las Vegas casinos where he spends most of his time. A rainbow collage of blown-glass flowers, modeled on the installation in the lobby of the Bellagio, hangs over the foyer; a 1,100-gallon curved tropical-fish tank, similar to the massive aquarium at the Mirage—and built by the same company—forms the base of the staircase in the entryway; and the marble tile on Greenstein's bathroom floor matches the pattern in the Venetian's suites. He went so far as to take a cue from casino mogul Steve Wynn and create a miniature in-house art museum, though Greenstein stocked his with reproductions of the world's most famous paintings rather than investing in lesser-known originals. "Who wants to look at a painting they've never heard of?" he asks.

Greenstein, who had dominated games throughout the Midwest and California for more than 30 years, was virtually unknown in Las Vegas, the poker capital of the world, until he first challenged the Big Game in 2001. Headed by card-playing legend Doyle Brunson, the Big Game is the pinnacle of high-stakes poker, with pots so huge that fewer than a dozen players worldwide have the bankroll and skill to survive in it. To Big Game habitués, Greenstein initially appeared to be one more rich guy who would blow into town, drop a bundle and promptly disappear, making room for the next fish.

"I always say it's impossible to come from out of nowhere and play at the highest levels," says Eric Drache, a veteran poker pro who organizes the Flynt matches. "It would be like trying to become the heavyweight champion of the world if you'd never fought anybody any good. But that's just what Barry did. He came into the Big Game and started winning every day. Barry got a lot of heads shaking."

If they had known a little more about who they were dealing with, the poker cognoscenti might not have been so surprised.

When he was a young boy, growing up in the Scottsdale neighborhood on the west side of Chicago, Greenstein scored so high on his IQ test that his father, a grammar school principal, complained to the school board that the test had to have been flawed. Though young Barry never studied, he still managed straight As and a perfect score on the math portion of the SAT. During his senior year in 1972, his calculus teacher gave him some computer terminals and a manual and suggested he tinker with them over the weekend. On Monday, Greenstein returned with a program he had written that made it possible to play 18 holes of golf on the computer. After that, the teacher let Greenstein spend most of his class time writing code, but still rewarded him with an A in calculus.

Relentlessly ambitious and eager to prove he was more than a scrawny nerd with glasses, Greenstein also made himself into a varsity wrestler, a scratch golfer and a star of the baseball team.

Poker profits began to roll in when he was 12 and caddying at a local golf course. His highly profitable gaming escalated during the later years of high school, after weeknight tutoring sessions devolved into blasts of Five-Card Draw and Seven-Card Stud. Greenstein and his classmates first played for quarters, but the stakes quickly rose. In college at the University of Illinois at Urbana-Champaign, he found soft games with local businessmen and was able to cover a semester's tuition in a good night at the table.

With his combination of math skills, an unshakable work ethic and a dogged determination to succeed, Greenstein was well-suited for high-stakes poker. He recognized early on that even the most talented players were unable to control the wild ups and downs that are inevitable in a long game. He found that he usually made most of his money toward the end of a session, when other players were tired or steaming. One of his favorite games took place above a bar in a rough section of Decatur, Ill., where the action commenced around sundown and raged till dawn because the parking lot below was too dangerous to traverse at night. Greenstein fortified himself with bologna sandwiches, then pounced on his worn-down opponents when daylight approached.

By the late 1970s, as he neared 30, Greenstein was conflicted. He had been working toward a doctorate in math, which was his passion, but he was making more than $100,000 a year playing poker on the side. He bought his first Jaguar, moved into an expensive house and married a woman named Donna Doss, who shared his taste for the good life. Donna had three kids from a previous marriage, and Greenstein fought to gain custody. His lawyer, however, warned that his chances were slim. "You're never going to get custody as a professional gambler," the lawyer said, "and you don't make any money as a graduate student." Faced with the prospect of losing Donna's kids, Greenstein flew to California and looked for work in Silicon Valley's burgeoning software industry. In 1984, he signed on as the fifth employee at a company that later would be named Symantec. His salary was a measly $40,000—a sum that didn't come close to covering his standard of living—but he knew he could always supplement his income through poker.

"It was like a gift," he says. "When I wasn't making big money, poker was there. There is always going to be a poker game around the country or around the world, and I'll always be able to beat it."

While working at Symantec, now best known for its Norton antivirus software, Greenstein developed a broad range of personal computing products. He worked on one of the first search engines and almost single-handedly developed a word-processing program called Q&A that, upon its release in 1986 with Greenstein and family pictured on the box, was named PC Magazine's top word-processing program of the year.

By 1991, though, Symantec had grown from five employees to more than 1,000, its corporate culture had changed and Greenstein had grown weary of the bureaucracy. After seven years and countless round-the-clock work crunches at Symantec, he left the company—but not for another job. He was faced with piles of debt from living beyond his means in Silicon Valley, so he sold his remaining stock options and paid off creditors. All told, during his seven years at Symantec, Greenstein, amazingly, earned less than $1 million. He had packed up and moved to California in order to keep his family together, and now he needed to provide them with the financial security and comfort he felt they deserved. So he returned to poker full-time.

Greenstein is among the few top-ranked professional poker players with corporate experience, which helps explain why he manages his career differently from other high-stakes specialists. For starters, if he doesn't like the games, he goes home. His self-professed strength is what could best be described as game management. Like any good businessman, he identifies markets where he possesses an advantage and then moves aggressively to capitalize. To him, success at the poker table is determined less by how you play than when you play.

"The way you earn the most is to play against weak players who have a lot of money—that's how you really do well," he says. "I don't go out and say, 'Let me see who the best players in the world are, and I want to beat them just to prove I am better.' My thought is, 'What is the most lucrative situation I can get into and how can I exploit it?' "

It's initially surprising, then, that Greenstein has become a regular in the Big Game, as it's literally impossible to find tougher competition. Yet unlike a lot of players who have popped into the Big Game over the years just to say they did, Greenstein saw it as a legitimate money-making opportunity. He simply felt that he played as well as anyone and that it was where the stakes were the highest.

Greenstein admits that he loses about half the time he plays poker, but he generates huge profits by setting loose boundaries on his wins and losses in much the same way that a stock trader designs stop/loss orders. He wants to limit his downside without capping how much he can earn in a given night. This is harder than it sounds, as most players—even very good ones—instinctively ease up once they get comfortably ahead. When Greenstein is winning and faced with tired or inferior opponents, he doesn't relax or head home for a few hours of sleep; he ratchets up the pressure until he has squeezed every last $1,000 chip from his opponents' stacks.

Chip Reese, a Big Game regular and the youngest inductee into the Poker Hall of Fame, admires such tenacity. "I like to play, and I could win a million or lose a million—but if I get sleepy, I'll quit," he says. "However, when you are playing your best—and things are going well for you—your opponents are probably playing their worst and feeling unlucky. The right thing to do is to stay [as long as it takes] and win the money. Barry is good at that."

Greenstein is willing to stick around for hours, even days, until he bleeds his victims of the maximum amount of cash. That requires him to risk his hard-earned profits against desperate—and therefore dangerous—opponents, but it gives him the chance for a really big score.

"So many people are afraid to make money," Greenstein says. "They get ahead and start thinking, I don't want to lose all this back and look stupid. For most people, it becomes a self-fulfilling prophecy. They lose some of their winnings because they are protecting. I am going to turn a win into a loss sometimes. But I also know that I may very well take a $300,000 win and turn it into an $800,000 win. I do it often enough that I have to stick it out for hours on end when people are playing bad and dumping their money."

After poker became a national obsession in 2003, it migrated from backrooms to living rooms virtually overnight. As recently as 2002, high-stakes players had to practically beg poker room managers for dinner comps. By 2004, they were being paid $10,000 to wear logos on TV. This transformation was largely due to the World Poker Tour. Suddenly, thanks to scripted commentary and sharp editing, run-of-the-mill grinders came off as superstars. Self-consciously bookish Howard "The Professor" Lederer and backgammon wizard Paul Magriel—known for his confounding tics such as muttering "quack, quack" before betting—turned into minor celebrities. Bad guys, such as the bullying Brit David "Devilfish" Ulliott and bratty Phil Hellmuth, practically became household names.

Around the country, seasoned pros rejiggered their public personas. They hired publicists and managers and shamelessly hammed it up for the cameras. Greenstein, though, was unimpressed by the posturing. He disdained tournaments as a distraction. After all, he played for fortune, not fame, and knew that the biggest and most consistent money would always be in cash games. "I looked at tournaments as an ego weakness," he says. "So I intentionally didn't play in them."

But the WPT's ascendance in prestige dovetailed with Greenstein's blistering performance in the Big Game. He now was a millionaire many times over and providing a comfortable, some would say extravagant, lifestyle for his family. He also felt his kids were overly materialistic (though divorced from Donna, he retained joint custody of the three children from her previous marriage and the two they had together), and that they failed to understand how privileged they were in relation to others around the world. He decided to rectify that with a grand plan: play in tournaments and set an example by donating all of his tournament winnings to charities that help children.

Greenstein did not abandon his bottom-line mentality—he simply pledged to direct a portion of his poker riches toward a higher purpose, just as hugely profitable companies establish philanthropic divisions when the corporate coffers are overflowing. The timing was perfect for Greenstein, as playing poker for nothing but his own gain had turned into a soulless and debilitating grind.

"I am allergic to cigarette smoke," he says, "and at times I looked at my life like Christopher Walken's character in 'The Deer Hunter,' where he would play Russian roulette for money and send it back to his crippled friend and his wife. He saw that his life was worthless, but he had a purpose: to make money and send it home. I knew I was slowly killing myself sitting in these smoky rooms, but I just put my head down and played."

Rejuvenated, Greenstein captured a Seven-Card Stud tournament at Flynt's casino in March 2003, and thereafter donated more than $400,000 to Children Inc., a Richmond, Va.-based nonprofit organization that aids impoverished kids around the globe. Nine months later, he made his first final table on the World Poker Tour. He started as the chip leader over a table of less accomplished players, with the notable exception of his Big Game rival Chip Reese.

From the outset, Greenstein viewed Reese as the sole obstacle between him and the title, so he targeted Reese early on by raising almost every pot in the opening rounds of play. Because Greenstein sat on Reese's right—meaning he was usually in position to act first—Reese was effectively forced to wait for big hands or risk his tournament on a bluff. Greenstein bet so aggressively that Reese rarely stayed in long enough to take advantage of a cheap flop—in Texas Hold 'Em, the "flop" comprises the first three community cards that are exposed after an opening round of betting—at which point Greenstein could then out-maneuver the less-experienced players at the table. On the one occasion Reese came back over the top with a re-raise, Greenstein simply folded. His goal was to slowly whittle down Reese's chips by stealing blinds and antes. Greenstein remained in total control of the tournament and steamrolled to victory.

He gave the first prize—$1 million—to Children Inc., raising his total contributions to the organization to $1.4 million. He subsequently donated an additional $1.5 million in tournament winnings to a variety of charities, including his old high school, a children's hospital and Guyana Watch, which provides medical assistance to kids in that South American country. WPT commentators Mike Sexton and Vince Van Patten gushed about Greenstein's philanthropy and dubbed him "the Robin Hood of Poker." That moniker, and the resulting publicity, catapulted Greenstein out of the shadows and into the spotlight. Most surprisingly, at least to him, was the indescribable joy he felt in giving away his hard-won money.

"For the first time, I felt like I did something good for the world," he says.

Greenstein now is semi-retired from the lucrative cash games that furnished his fortune. These days, he expends most of his poker energy on the tournament circuit but, because he gives away 100% of his tournament winnings, he needs to play in cash games occasionally to cover expenses—such as the ongoing renovations to his house. Further, the government allows him to deduct only 25% of his income as charitable contributions, so he could end up paying taxes on money that he gave away. As a result, he needs to earn several hundred thousand dollars a year in cash games just to cover his tax burden. Which explains his sporadic appearances in Gardena to play with Flynt and the others.

At 5 p.m., an hour after the Flynt game was scheduled to kick off, the host rolled up to the table in his gold-plated wheelchair. Sporting a powder-blue V-neck sweater, with his reddish hair combed back neatly, he appeared almost grandfatherly. Flynt has been in a wheelchair since a white supremacist shot him with a deer rifle in 1978 for publishing an interracial-sex photo. Because of his disability, his dexterity is limited and he can't look at his cards without exposing them to the rest of the table. To protect against less-than-honest opponents, a bodyguard positioned two 6-inch-high wooden slats in front of Flynt, forming a makeshift barrier behind which he could survey his cards.

Flynt prefers Seven-Card Stud, so that was the brand of poker they played for more than two days, stopping only when Flynt tired. The stakes were such that, over the course of the game, each player could possibly win or lose more than $1 million.

Greenstein started playing in this game seven years ago, when it was held in Flynt's Hollywood Hills home. Flynt keeps his house as cold as a meat locker, and players would have to bundle up in thermal underwear before arriving. As always, Greenstein felt like his determination gave him an advantage in adverse conditions—in this case, the freezing cold—and he needed a psychological edge because he knew almost nothing about Seven-Card Stud at the time. Greenstein and Flynt became close friends, but Greenstein still takes pains to flatter his host.

"Larry built this place with his poker winnings," Greenstein said of Flynt's casino, an obvious lie that Flynt indulged with a wry smile.

The game gradually gathered momentum and the banter subsided. Action moved rapidly, with each player giving less than a second's thought to folding, calling or raising. There were none of the drawn-out, anguished decisions that mark televised poker. If Greenstein was bluffing, he didn't boast about his brilliant play. If he was sitting on a monster hand, he gave no indication of that either. Like all high-stakes cash games, this one promised to be a marathon, not a sprint, and Greenstein refused to give anything away during an early leg of the race.

Greenstein won three five-figure pots in rapid succession, inflating his already large chip stack. He appeared to be in perfect control of the table, even though he was falling behind Ivey in a series of so-called prop bets, in which the players wager on which three-card combinations will appear face-up. Each bet, according to the skyscraping stakes they had established, was $5,000—though the payouts doubled and tripled in certain situations.

After a queen came up—a good card for Ivey—Greenstein casually tossed his friend a $5,000 chip. With a flip of his hand, Ivey indicated that Greenstein owed even more. (One of the main tenets of playing props is that you have to pay only if your opponent demands to be paid; that is, if a player is not paying attention, he can't win. Which is one of the reasons Greenstein and Ivey play props. It forces them to stay actively engaged in the game even if they are not involved in the hand.)

"How much is it?" Greenstein asked.

"$15,000."

"Oh," Greenstein said, tossing two additional $5,000 chips. "I thought it was $25,000."

"You thought you owed me $25,000 and you paid me $5,000?" Ivey asked, incredulous. He knew Greenstein was merely testing him to make sure he was paying attention, but he couldn't resist the chance to jab at the man's rosy public image. "OK, Mr. Robin Hood."

The dealer slid out the next round of cards and the game marched on. With Greenstein's chip stack having increased only incrementally, a million-dollar Labor Day weekend win appeared unlikely, but a six-figure payoff was well within reach. Greenstein folded his hand, leaned back in his chair and shook his head. He smiled broadly. It almost looked as if he was having fun.

This article is a reprint from the Los Angeles Times. To view the original article, click here.

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