Grace Through Gambling: Matt Lessinger '96

Take his first publishing effort, The Book of Bluffs (Warner, 2005). It does in 11 smart chapters what Mike“The Mad Genius of Poker” Caro did in his classic, Caro's Book of Poker Tells, in 1984. ( A“tell” is a psychological read of opposition gamblers' body language, which enables the astute player to out-think them). And Caro's book became fundamental to poker players caught up in the gambling explosion that hit the country beginning in 2003. Aside from all the current noise about Las Vegas (William Petersen and James Caan on TV) , there was the burst of Indian reservation casinos, beginning in the '80s; the spread of mini-Vegases, first in Atlantic City, then in Connecticut, Missouri, Florida, and the Gulf Coast (the latter unfortunately wiped out by Katrina); and more recently, the profusion of poker clubs in California—a state that rejects the tawdry aspects of casino culture, but has lots of folks with money to burn who love legal risk, and so just play in tasteful venues featuring poker's various varieties.

Matt, for example, who has elevated the art of bluffing in poker, has been hired by the Oaks Club, outside of Oakland, as a“prop player” (house pro), staked in games and paid a salary, to make sure individual contests are“interesting”; he's not a dealer, but a pro participant who plays in ways to keep the competition level up and the games full. So that even if he hits a bad streak of cards, 10-high, say, in a game of seven card stud, he'll study his opponents and if he thinks it's warranted, bluff his way to the pot.“Bluffing is the sex appeal of poker,” he explains.“I wanted to do for bluffing what Caro did for tells.” So far, he's sold 26,000 books in three months. And that's without a major campaign.

The Book of Bluffs explains 49 sample bluffs, some from Matt's own experience, some from generic classics, actual games the author witnessed, or stories told him by other pros, kicking back after the action...His goal is to get the reader constantly thinking of bluffing, not just resorting to it when forced to, in contradiction of the native wisdom of poker betting, which advises caution at all times, and makes for long games, small pots, and frequent folding, even if your chips are piled high:“Playing that way would bore me to tears,” Matt says.

A classic bluff was the World Series of Poker victory of then amateur Chris Moneymaker (!) over old pro Sammy Farha three years ago. This was in Vegas on the fifth day of a grueling“no-limit hold 'em” tournament, at 1:30 a.m., breakfast time for Sinatra wannabes. ESPN was covering, and using“lipstick” cameras for the first time on national television. These are slim-tech devices that allow home TV watchers to see the cards the players aren't showing. So for example, the“board on the turn” (upturned common cards, which both players can use in no-limit hold-'em), showed a nine of spades and a two of diamonds, a six of spades and an eight of spades. But TV watchers could also see Farha was holding (not showing) a queen of spades and a nine of hearts, top pair and a queen high flush draw. He bet $300,000.

Behind his mirrored shades, young Chris looked at the pro, and started to move his chips up.

“You call?”“ asked the dealer.

“No, I raise,” the amateur said quietly,“five more,” and pushed $800,000 into the pot. The lipsticks showed Chris was holding a king of spades and a seven of hearts—an open-ended straight draw and a king-high flush draw. But really all he had was king high.

Farha called:“We said it's going to be over soon,” he smiled.

The“river” card (last common card dealt) was a three of hearts. It wasn't likely to help Moneymaker. The pro stared. He still had top pair and a decent kicker (the queen). He checked (held).

The amateur had missed his flush with the three of hearts. All he had was his old king. But he didn't miss a beat:“I'm all in,” he said, meaning he wanted to bet everything. Farha had $2.5 million left, and Moneymaker had enough to cover.“That would be a tough, tough call,” announced ESPN's commentator, Norman Chad, noting that the pro would now have to put in all his chips, and if he lost, wash out of the WSOP .

“You must have missed your flush,” Farha tried on the kid, but Moneymaker sat there like an Easter Island profile. The art of the bluff defined.

Farha waited what seemed 20 minutes, then folded.

The crowd went postal.

“And poker was born as a national TV sport,” Matt Lessinger declares.

Never eat at a place called“Mom's”; never play cards with a guy named“Doc”.

Matt's father, Victor, an investment sales manager and senior vice-president for First Investors Corp. in New York state, expected his son to follow in his footsteps. But Matt, while enjoying the“small classes” and“open exchanges” of his Haverford economics major, and recognizing in himself a penchant for dealing with what he calls“probabilities,” found some of the teaching boring, and not conducive“to setting you on a career path.” Although he quickly took a job after graduation with Sanford Bernstein Investment Research and Management as an associate portfolio manager, he soon realized it wasn't for him. He'd been driving down to Atlantic City with some of his buddies on weekends for awhile—“I'm from the Bronx,” he explains,“Yonkers racetrack was within yelling distance—so I guess gambling was in my blood.” Matt applied first to Resorts International, then the Claridge, but they weren't impressed with his four-star degree: he didn't start as a floor boss or pit manager, which he vaguely had in mind. Instead, Resorts sent him to vocational school to learn to play craps and deal blackjack, and then he picked up poker, baccarat, and an Asian game called pai gow. In six months he was promoted to dealer. At 22, he was a floor boss.

“Why did I do it?” he says rhetorically. A.C. was a good place to learn the gambling business, but there wasn't a lot of accessible action:“You had busloads of retired folks coming in to play for $20 or $30, then they're back on the bus to Vineland, N.J.! I liked being around working-class people, I liked the casino lifestyle, which is attractive and stylish, but the other side of that was you had the Monopoly board names—Tennessee Ave., New York Ave., as virtual crack alleys”; the areas away from the casinos were grim with sleaze. And the big-money high-roller games, that did attract the best players in poker—Doyle Brunson, T.J. Cloutier, Bobby Baldwin, Harpo Burton, Barbara Enright—were so expensive they were“closed.” So if you wanted a shot at the biggest pots, you needed Bank of America behind you.

Matt hung in until he figured he'd perfected his game, escaping the A.C. blahs—“It's got low energy and is cold and rainy a lot of the year”—by first moving to Brigantine, a classy little island community just to the north of Atlantic City—and then heading west to Las Vegas, the world capital of gambling. His mom, Anita, who believed in working at something that made you happy, supported him from the beginning, but his dad was skeptical and disappointed at first. Matt won so many games and finished well in enough tournaments in Vegas (“where the poker was medium-tough compared to A.C.—where the games were hard”)—and California, where the poker is relatively easy, that Victor came around:“When my father saw that I was making a good living [and not going down some movie path to hell], he was okay with my lifestyle. Poker players used to be viewed as degenerate gamblers living sad lives in back alleys and playing in shady places...Now [poker] is practically a respected profession; poker players have written books, made countless TV appearances, and are all over the media.”

Matt was happy in Vegas, but his girlfriend, a Haverford student, wanted to go to grad school,“and no way was she going to live in Nevada.” So he moved to northern California, to Alamo, 20 minutes east of San Francisco, which he describes as“God's country.” From there, he regularly hits Vegas“for the adrenaline rush,” the upbeat younger players and corresponding atmosphere they create (recently, he played“socially” over a Vegas weekend, and still came home an $850 winner). But his job at the Oaks Club grounds him on the left coast, playing cards from 6 a.m. to 2 p.m. three days a week (plus he gets the medical plan!)“When I come in, a lot of [patrons] have been playing all night, so they're beat, and I'm fresh...” His voice has a kind of wink in it.“Some of them will work all day, start playing around 8 at night, and just play through till their shifts start at 9 a.m. That's what you call people with ´gamble'.”

Revenue streams for postmodern poker players are 50 times as lucrative as they were when Nelson Algren created“Frankie Machine,” the dealer in his 1949 novel The Man With the Golden Arm, a Division Street hustler in Chicago's Polish west side ghetto. Where Frankie, hooked on morphine, hustled for a percentage of Schweifka the Backer's game, played in a seedy room a flight above an alley that would have made Atlantic City's coarser venues seem posh, postmodern gamblers can publish books, write columns for Poker Digest, Card Player, and Online Poker News (all of which Matt does).

As a tournament winner—he's won the 2000 Carnivale of Poker pot limit hold 'em championship, and finished second in the Sam Boyd Classic in Vegas for no-limit hold 'em—he expects to write more books, and possibly do some TV commentary. But the biggest change from the old days is Matt's ability to play online as well as in“B & M” (Brick and Mortar) cardrooms.“You can be playing on four or five tables at once online,” he explains, as opposed to being in only one game, live. Such multi-tasking calls for youthful mental agility that won't allow for long“leisurely” careers, such as those of the patriarchs of poker, Johnny Chan and Amarillo Slim. But at 31, Matt's got some time.

— John Lombardi