Cigar Aficionado

In the driveway of a hilltop homein Brentwood, California, the Tesla is charged and loaded. A bottle of 12-year-old Hibiki Whisky resides in the trunk alongside a six-pack of good Bordeaux. Arturo Fuente Hemingway Short Story cigars top the console. Big band and classic rock have been programmed on the sound system. Professional gambler turned hedge-fund whiz Rob Reitzen is driving. I'm riding shotgun. His company's CEO Larissa Posner has the backseat all to herself.

The plan sounds simple: Road trip to Vegas, eat and drink well, make a little money at blackjack, revive PokerGirl. The latter is the real order of business, but it's also the diciest part of the trip. Beating blackjack and dining out are easy. "Ramping up PokerGirl," Reitzen says, "may present a problem."

PokerGirl is a relic from the glory days of online Texas Hold'em. It is the name under which a protégé of Reitzen's won hundreds of thousands of dollars by playing the game like a computer. She was in her early 20s, had previously been a waitress at Arnie Morton's steakhouse in Beverly Hills, went by the name Lary Kennedy in real life and learned to crush online poker games the Reitzen way. Then she was accused by Full Tilt Poker of actually being a computer. Her was frozen, $80,000 was seized by the website and TMZ actually did a story on the imbroglio. Lawsuits ensued and things got ugly amid accusations that she played under multiple identities.

She filed a lawsuit against Full Tilt in 2009, claiming, among other things, fraud, libel and unjust enrichment. At the time, it seemed that Full Tilt could deem any player a "bot" and withhold winnings at will. The case was eventually dismissed and she never refiled.

This was before Black Friday in 2011, the outlawing of online poker in much of the United States and Full Tilt's ultimate insolvency.

But it's nine years since PokerGirl bet her last street and the online landscape has changed dramatically. Reitzen isn't even sure if we will find a suitable game to play on the screen of my MacBook Pro. "There's a chance that we'll be stuck buying in for dinky stakes," he says. "We won't have a decent sample size [because we're not in town for very long] and we may not win."

Is he concerned that her long, profitable approach to poker won't work under today's conditions? "No," he says. "That'll be fine. The math remains the same. And it's perfectly sound."

But, as we prepare to pull out, Reitzen is not focused on any of that. He's leaving behind three computer engineers who'll spend the weekend programming strategies for his fund, Time Series Solutions. They'll work on ways of beating Wall Street by finding quantifiable patterns in the markets and capitalizing on them. He gives his guys hugs and marching orders. Then we pile into a car that practically drives itself.

As he hits Interstate Highway 15 and noses his automobile toward the Mojave Desert and Las Vegas, Reitzen explains that he spent a couple of lackluster years as a math and probabilities major at UCLA. Along the way, he found The Cincinnati Kid to be inspiring and nurtured a natural fondness for poker. So much so that, in 1979, he asked a girlfriend's Hold'em-playing roommate to loan him a book that would help improve his game. The notions of training neophyte players and leveraging the game into a high-volume business were the furthest things from his mind. Reitzen just wanted to play smarter at the L.A.-area poker clubs.

Due to a mix-up, though, he received a volume called Playing Blackjack as a Business by Lawrence Revere. "I thought it was interesting and learned to card count," says Reitzen. "I started making trips to Vegas, improved my skills and built my bankroll. Eventually I ed a team."

During those nascent years of the home computer, a teammate of Reitzen's got his hands on one of these seemingly miraculous machines. That man would go on to create the brilliant computer system that yielded hundreds of millions of dollars for a group of horse bettors in Hong Kong. But back in the early '80s, he and Reitzen were happy to create plays that paid off with far less remuneration in blackjack. They refined strategies that decimated games in Las Vegas and beyond.

Reitzen and his partner invented custom counting systems, devised methods for cutting to certain cards that would be advantageous to players or disastrous for dealers, improved techniques for memorizing sequences that could be recognized in future shuffles. They racked up their share of million-dollar weekends and terrorized casinos around the world. It was a good time to be playing blackjack. Profits rolled in.

The promise on the back of Revere's book—that if the reader learns these strategies, he will be able to fly around the world for free, stay in fine hotels, eat gourmet meals and come home with a profit—was being realized by Reitzen. He re a particularly colorful few hours of playing in Amsterdam. "It was an underground gambling club in every sense of the word: situated behind a pharmacy and down a flight of steps, so the place was literally subterranean," he re. "There was craps and blackjack and a sign on the wall with various exchange rates. Then they had another room where people were fucking on stage."

Reitzen did his best to focus on the cards. He was there to play, and play he did, tidily winning some $20,000 without breaking a sweat. Then he heard one partner say something to the other. "He spoke Italian and I asked the guy I was with—who was backing the play—what had been said," relates Reitzen. "I was told that he asked if I was card counting. Then I wanted to know how the other answered. My backer said that he replied, ‘The American ain't counting shit.' "

Nevertheless, the next day, when the casino owners offered to send a limo for Reitzen, he refused. Much to the consternation of the backer, Reitzen did not play the underground den again. Soon after, though, he had more of a life-changing blackjack experience in the men's room of a small Nevada casino where he and another player, not known to him, were both counting the decks.

Stepping away from a urinal, Reitzen whispered, "The big C."

He saw it as a subtle way of signaling that he realized they were both counting cards.

Surprised, the player replied, "Oh, you're using one, too?"

Reitzen re being a little puzzled by the comment but he was shocked a second later: "The guy pulled down his pants, showing a jockstrap with batteries and wires running out of it. He was all wired up with a small computer inside the jockstrap. Wires ran down to his toes where there were switches that allowed him to tap in the cards as they were dealt. Then he had sensors attached to his genitals; the sensors gave off pulses, signaling him on how much to bet and the plays to make. It was completely amazing! I told him I was just counting in my head and he nodded. He told me he wondered why I made a few mistakes."

The trip turned out to be a losing one for Reitzen, but he left with something more valuable than cash. "I headed home enthralled with the computer. Not long after, in like 1982, I got one for 10 grand, but we eventually had the sensors moved to just above our ankles."

Without knowing it, Reitzen had stepped into the golden age of what would become known as "computer play." Casinos had not yet thought to make the use of computers illegal and a former Raytheon engineer hated casinos enough to outfit players with machines that allowed for perfect counting and shuffle tracking. The builder was Keith Taft, a born-again Christian who found gambling ts to be evil. Reitzen is agnostic where religion is concerned, but, as far as computers went, he became an instant believer. In fact, it would be fair to say that he went computer crazy.

Reitzen and his forward-thinking partners recognized that computers could be used to leverage their advantageous gambling operation and turn it into a real business. "We had a slot-machine team that played in a profitable way derived on the computer," he says. "People were wearing computers to beat blackjack and there was work being done on roulette. We were beating sports and the stock market. Then there was poker. . .We figured out that, on the flop, it is correct to bet based on a range of hands rather than on specific cards that you hold. It allows you to give away the least amount of information while gaining the maximum amount of unit-expectation. This runs counter to what most players do. Another system helped us to beat lowball."

Technology made gambling into a profitable blast throughout the 1990s. Reitzen stocked up on collectible wristwatches, he ed the Beverly Hills Grand Havana Room and drove around in a Bentley. He and his group bankrolled blackjack games in California casinos—state law once mandated that third-parties serve as the house in casinos that have certain types of licenses—and that provided a giant windfall. At some point they had 300 people playing and scouting and beating games around the globe. "Everyday I'd get reports on how we were doing," he says. "And let's just say that we were doing pretty well."

Then online poker hit, PokerGirl served him a steak at Arnie Morton's and things really blew up.

Hours after arriving in Vegas, we're showered, changed and crowded around a table at the Sin City version of New York's Carbone restaurant. Eighties music plays from the speaker system, waiters in retro uniforms take orders, a rum cart makes the rounds and the place feels transported from the set of Goodfellas. At the table are Posner and Reitzen; Hein Hundal, an engineer who worked for Reitzen on the poker project; a mathematician who goes by the name Duke and another engineer known as The Kid. Guest of honor is Lisa Arnold, a diminutive Chinese woman with oval-framed eyeglasses, a baggy sweater and a scarf around her neck.

She looks harmless now, but 10 years ago, you would not have wanted to confront her across an online heads-up poker table. She logged in under the name RedGard1 and ranked among the game's deadliest assassins, playing heads-up limit poker for stakes as high as $100/$200. When she first met Reitzen, she barely spoke English and knew nothing about the game. Between 2002 and 2010 (playing the last of those years in London after online poker was outlawed in the U.S.) she won nearly $8 million.

A 1990s émigré from China, Arnold was originally put in touch with Reitzen via a mutual friend. Reitzen hired her to work on his slot-machine team, beating progressive slots by playing them when the jackpot exceeded a threshold that would ensure a positive financial expectation. Eventually casinos got wise to the ploy and rousted her from the premises.

Arnold thought she was out of a job, but the opportunity was actually shifting into high gear. Since the earliest days of online poker, Reitzen and his team had been using hundreds of non-cheating, game-theory-programmed computers to beat humans on various sites. Site owners knew this wasn't good for business. They designed software for sniffing out the bots and, by 2002, began to shut down their s.

Undaunted, Reitzen decided to turn humans into computers. "That's when Rob told me to learn poker," Arnold says, sipping wine and working through an enormous slab of veal parmigiana. "He gave me a machine to play against. It told me when I made mistakes and showed me the game. Then, when I got good, Rob tested me."

RedGard1 crushed poker. Sharp as she was at the game, however, Arnold could not have realized that the strategy she employed cost Reitzen millions of dollars to create. It was designed over the course of decades, with loads of engineers.

But the real ingenious part of the whole thing was how Reitzen made it easy for anyone to play like a computer. “I had 20 clock faces that compressed the strategy for humans to cover Hold’em situations,” he says. "The faces were made of cardboard and fit under the hands of standard-size clocks. All you had to do was find the clock that described your situation"—say, a big pair in the small blind—"and make whatever play the second hand told you to make. That moving hand provided randomization. You always made a correct decision and played with enough variation that opponents could not figure out what you were doing. We turned the seemingly intuitive game of poker to the totally rote game of blackjack."

Things were going fabulously well for Reitzen and for more than 100 players employed on his poker team. They worked from home, video-cameras monitored their play, Reitzen backed them and they kept percentages of their winnings. Then something unexpected happened: Full Tilt began accusing the players of being bots. Their s got shut down. "I reached out to a Full Tilt partner and tried proving to him that my players were human," says Reitzen. "I sent in the clock dials and explained how they played. I even offered to show videos. He didn't care. He said they played like computers, so they were computers."

Arnold had some $80,000 confiscated from her and Reitzen had enough. Soon after all of this, he mothballed the poker enterprise and focused his attention on Wall Street. Arnold continues to find poker profitable, but now she antes up in Pacific Northwest casino poker rooms, near where she lives, and plays face to face with humans. Lawsuits designed for recouping money came to nought and the operation completely ceased. "I always had a soft spot for our poker team," Reitzen says, calling for a check and last pours of Cognac. "I do miss it a little."

An afternoon later, we convene in a room at the Cosmopolitan. Reitzen has brought his clocks. My laptop is open. Lisa Arnold is aboard for coaching. The idea is to log onto a legal online poker site in Nevada, myself as PokerGirl, deposit money and rev up the old engine. The intention: profit at poker. However, there is a problem. Heads-up Limit Hold'em, which this system is specifically designed for, is a ghost town. There is no one to play against. We're sitting alone at a virtual table, feeling a little bummed.

Then we devise a workaround for playing on a site that might have the appropriate action.

"Because your bankroll is so small, we have to play cheap," Arnold says.

"No problem," I tell her. "This is not about making money, it's about winning something by playing the Reitzen way. It's proof of concept."

There are plenty of tables with stakes of 10-cents/25-cents. It'll be a gas just to deploy the strategy. My avatar settles down at a heads-up table and another player immediately s us. I prepare to wipe him out. Then something strange happens. The player is remarkably good. He bluffs at all the mathematically correct times, he traps when he should and rarely folds. "He's playing close to game-theory optimal," Reitzen marvels.

Several hands in, my opponent leaves the table and is immediately replaced by another one who also never misses a beat. "They're world class," says Lisa. "They're too good to be playing at these low stakes."

"They're bots," Reitzen declares. "We're playing against computers. The site is infested with them."

We stick around for a while before agreeing that it's useless. The game has changed. Bots have taken over the tables that Reitzen's humans once dominated. There's a lot of chattering, reminiscing and ing of the Hibiki. Reitzen gets quiet and watches a bit of the higher stakes, no-limit ring games. "There are definitely no bots there," he says. "We made it halfway to finishing a no-limit program and never managed to get it done."

Soon my computer is shut down, the clocks are packed up and the air hangs heavy with resignation. But just for a while. By nightfall, all of those feelings are shaken off. We're in a private dining room at an off-strip casino with some high-roller friends and a couple of card-counters. We eat too much, drink too much, laugh too much, take advantage of casino largesse and make many toasts to PokerGirl and RedGard1.

Things proceed to get rowdier in another casino where we commandeer a blackjack table, count cards blatantly and puff away on cigars. Maybe it's thinking about old times, but Reitzen verbally replays a few hands from the no-limit games he saw online. He points out mistakes that had been made and wonders when the U.S. will legalize the Internet iteration of poker. "I think I'm going to finish working on no-limit poker," he says suddenly, putting up a purple chip for the next hand of blackjack. "I'm sensing an opportunity. I think we can make some real money again."

The sentiment warrants yet another toast. 

Michael Kaplan is a Cigar Aficionado contributing editor.