Logic Problem

Alan Boston meets me at his favorite Chinese restaurant, on the west side of Las Vegas, and I ask him how things are going. "It's been a rough year," he says, settling in at a table near the rear of the sleek eatery. "Tonight we lost three games at the buzzer." And that's the way things seem to keep falling for him: "A lot of it is bad luck. You can't handicap teams hitting three-pointers from half court. The random losses have been outside the bell curve."

In the realm of professional gamblers, Boston is an odd duck. Talented and analytical, he's been successful at handicapping sports (mainly college basketball), makes money as a no-limit hold'em player, and has generated a few bucks betting on horses. Howard Lederer once partnered up to back a sports-betting enterprise with Boston as the brain. And for more than a decade, Boston worked as a handicapper for über-bettor Billy Walters. At age 48, though, Boston expresses little interest in continuing to do this thing that has been his core income for the last 20 years.

Buff, intense, and obviously brainy, Boston recently discovered that there is more to life than beating the bookies. "Other things have become more relevant," he declares, pointing out that the driving force here is his mentoring relationship with a young man named Rob, in his early 20s, whom Boston met while summering near Old Orchard Beach in Maine. "I've become like a father to this kid. It makes gambling bullshit. So I know how to pick basketball games? Big deal."

The rub, of course, is that Boston needs to bet in order to earn a living. And even if he landed some unimaginably huge score, you have to wonder how he would survive without the rumble of pointspreads cushioning his brain.

A waiter comes to take our order, and Boston glances at his ever-present sports pager. He checks a score and shakes his head. "My instinct was that I had the wrong side, and I did," he says. "I got all hyped up over numbers. F—-. I really lost my way here."

Alan Boston first got exposed to gambling when he was 8 years old and living on the outskirts of his namesake city. He remembers that his father used to take him to the racetrack, and it was there, by the age of 13, that he displayed an instinct for handicapping. He graduated from the University of Pennsylvania (Penn), where he majored in biological basis of behavior and minored in card counting and poker. After a stint of clerking for bookmakers in the Northeast, Boston headed to the West with an interesting, but vague, offer from an acquaintance: Come to Vegas and we'll make money.

Sensing an opportunity, Boston spent the summer of 1987 putting together power ratings for the coming college football season. Much to his delight, he proved to be a natural, hitting an unusually high number of winners, making his partner very happy and establishing a reputation for himself. He played a bit of poker, made the final table of his first seven-card stud event at the 1989 World Series of Poker, finished third in stud in 2002, and, once again, showed in 2004's H.O.R.S.E. tournament.

He'll be playing some of the stud events at this year's WSOP, though he thinks the romance has been squeezed out of the Series. "Mickey Appleman called the World Series a 'convention of gamblers,' and that's what it was," says Boston. "Now, though, it has nothing to do with poker or with gambling. They chop out way too much money, they won't serve me a Red Bull, and you can't say f—- at the table without getting a 10-minute penalty." He hesitates for a beat, then sums it all up by saying, "Corporate cliché and corporate conformity kill."

Feelings toward modern-day Vegas notwithstanding, poker's always been a cool game for Boston. But sports has long reigned as his bread and butter. Right from the start, he succeeded by approaching handicapping differently than most everyone else. It went beyond his power ratings. "I found that rhythm, that flow, that zone you need to get into to be great at anything," he says. "I'd wake up in the morning and react to what I saw. My instinct totally consumed the bet." He became the Michael Jordan of college basketball betting, turning sick moves into stunning profits, seeing things that the computers and number mavens just could not factor. "Athletes talk about the games coming to them. Well, the games came to me."

Word of his prowess eventually reached Billy Walters, the man who is often recognized as being the biggest, sharpest sports bettor in the world. Boston began working as one of Walters' college football handicappers in the early 1990s and did it into the next decade. "I gave Mr. Walters what I liked each week and kept my mouth shut," remembers Boston, explaining that he sometimes failed at the latter. "My buddy in Philly enjoyed betting $50 a game. Why couldn't I tell him what I liked? Then, one day, I got a call from Mr. Walters. He told me that I must be talking to somebody. I told him that I shared picks with my friend."

Displeased, Walters tried resolving the issue by giving Boston a list of games and suggesting that he share those with his friend in Philly. Boston complied, and soon thereafter received a call from Walters, telling him that he did a good job and that a crew on the East Coast had just taken big positions on those rogue picks. "What's unbelievable is that Mr. Walters found out," continues Boston. "But he always finds out. He's a very smart guy. I told him that I appreciate his treachery."

Since leaving Walters, Boston has bet sports with a partner (he won't go into detail) and capitalized on the battalions of weak players who have been drawn to the no-limit hold'em tables around town. He plays mostly low- to medium-stakes games ($2-$5 no-limit up to $25-$50 no-limit when the situation is right), and has had a lot of success. He employs the same intuitive style that powers him at sports. Viewing poker as a logic problem, he plays tight but aggressively, and goes against the grain of the all-in meisters who seem to be everywhere these days.

Boston illustrates his style of play by recounting how he handled a situation during a tournament at Red Rock that had been sponsored by Full Tilt (with which he has a relationship). First to act with A-K, Boston raised. He got called by Carlos Mortensen, sitting to his left, and Robert Williamson III, who was in the big blind. The flop came A-8-2, with the latter two cards being clubs. Williamson checked, Boston bet two-thirds of the pot, and Mortensen made a big raise. Williamson folded, and it came back to Boston. "Of course, the auto-move is to go all in, and you're probably the favorite; but I think you can do better than autopiloting," he explains, pointing out that his way of handling this situation baffled his old buddy Howard Lederer. "I was almost 100-percent sure that Carlos had a flush draw. I felt that he had A-10 or the A J. I didn't think he would make such a big raise if he happened to flop a set of eights or deuces. I called."

If the turn brought a blank, Boston knew he would move all in. But, it was another club. So, he checked – and so did Mortensen. Now Boston began to wonder if maybe Mortensen wasn't on a flush draw after all. Or, maybe he was trapping. The river card was an inconsequential 9, there was $160,000 or so in the pot, Boston had $75,000 in front of him, and he bet $20,000. "If Carlos had raised with K-Q or K-J or two jacks, I wanted to punish him," Boston continues. "But when he made a very small raise of $35,000, I folded. I know that you don't fold there for $35,000. There's just too much in the pot. And you can't let him bluff you for that amount, either. But I went with what instinct and logic dictated. In this instance, I thought I was right."

Was he? "I had no idea," Boston admits. "So, I knew I'd have to watch this tournament on TV. And if I was wrong, I would have really made an ass out of myself. So, I watched the show with clichéd baited breath. And, don't worry, he had the A 9. Go, Boston. You didn't go broke. Nobody plays a hand like that."

Boston sounds momentarily satisfied, but it quickly fades. He likens himself to his old buddy Stu Ungar, in that he succeeded at what he set out to do ­- become the best college basketball handicapper in the world – and now there's nowhere to go. "Mission accomplished," he says in a desultory tone.

Finishing the last of his dinner, sipping mineral water (he gave up booze and drugs long ago), Boston acknowledges that the accomplishment is flawed, that his touch for sports is often MIA these days. But, he adds, it comes back intermittently.

For an example of the latter, he explains how he wisely decided to take Stanford with 10 points against Oregon tonight. It begins with him remembering that Stanford previously played tough against Arizona for 35 out of 40 minutes, that Oregon would be coming in off a big win against Arizona, and that Oregon might be a little flat and doesn't like playing the half-court game that is a Stanford specialty. "Stanford gave Arizona fits, and they should be able to give Oregon fits; Stanford is a good bet for reasons that a computer programmer cannot come up with," says Boston. "That's understanding the game of basketball. That is your inner memory remembering a situation from the past that parallels the present. But if you're not thinking clearly or freely, when you lose endgame after endgame, your free-flowing, reacting inner self gets bogged down in all the ugliness and doesn't allow what I call flow to your thinking. When you're a free thinker who has no flow to your thinking, you're in trouble. The feeling I've had last year and this year is that I'm in a little bit of trouble."

Then, moments before the check turns up, Boston asks if I want to hear the ultimate irony, the very thing that defines him as a man and as a gambler. I nod in the affirmative. "Gambling," he says, "is my safety place. I've found my peace of mind in gambling. So if I lose every dime I have, it doesn't faze me." He gives the statement some thought, smiles slightly, then softly adds, "My safety place is risking everything I have. How's that? That's pretty f——— good."