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Long Balls & Long Shots

For many longtime gamblers, the challenge of beating baseball is irresistible

Last year's World Series, the intensely hyped battle between the St. Louis Cardinals and the Boston Red Sox, felt more like the Super Bowl than a baseball championship. At least it did if you were in the Mirage sports book in Las Vegas, which was packed with fans, screaming at the big-screen TVs, quaffing brews and betting like crazy.

A lone gambler stood in a corner of the room. But he wasn't screaming or drinking; he was simply staring at the screens in amazement as the last game wound down and it became increasingly clear that the Sox would become World Champions.

Months earlier, this professional gambler, who makes a fair bit of his income through sports betting, happened to be breezing through the sports book at a casino on the north end of the Strip. He looked up to notice that the Sox were posted as 50-to-1 long shots to win the World Series.

It was still early in the season, and the Sox were far from a sure thing. But there was one important element that made the bet alluring. "Everywhere else in town they were 25-to-1," says the gambler. "I immediately put $2,000 on Boston to win the Series. It's not as if I'm so smart about baseball, but this was just too good of an opportunity to pass up." Indeed, it made him $100,000 richer as the final inning of the fall classic wound down.

Historic World Series and 100-grand windfalls notwithstanding, however, in the great big universe of sports betting, baseball is a distinct underdog. It just doesn't generate the depth or breadth of enthusiasm and action that follows the endlessly moving point spreads of football and basketball. Baseball betting feels more cerebral, more mathematical, more of a dweebish challenge than either of the big two. With its seemingly endless season and countless statistics to track, it is best suited for serious bettors with the ability to focus. "You need to live, breathe and eat it for six months," says the single-monickered Fezzik, a professional gambler and guest host of the Vegas-based radio show You Can Bet On It. "You have to stay in the flow of the teams or else you get lost."

Because Fezzik sees opportunities in betting baseball, but can't really be bothered with the intricacies of tracking the sport, he keeps a couple of handicappers on his payroll, factors their picks, adds his own opinions and devotes his time to getting down wagers. Since baseball is most often built around a money line rather than a point spread—i.e. if you bet a favorite, you might have to put up $1.20 to win $1; the underdog would more or less be the opposite—it doesn't have some of the built-in excitement that comes with betting basketball and football (in which you give or take points). But it does offer selectively alluring opportunities.

Last year, for example, Fezzik noticed a proposition bet being offered at the beginning of the season: an over/under of 42 home runs for Alex Rodriguez. A-Rod had just been traded from the Texas Rangers to the New York Yankees, and Fezzik viewed the under as a no-brainer. "Yankee Stadium is a lot less favorable to him as a hitter," says Fezzik. "So every wiseguy bet him under, and he wound up hitting 36 homers." This year, Fezzik says, a hot bet will be the over/under on home runs for the league's top long-ball slugger. He figures it'll be posted at around 48. "But with nobody on the juice, I predict that number will not be made."

In more general terms, Fezzik offers a few broad tips for anyone who wants to make money betting baseball: "Playoff totals are always too high when the teams are competing in cold weather. The ball doesn't travel as far after the temperature dips down. Additionally, if the Yankees play an ugly team like Tampa Bay or Baltimore, the money will always go to the Yankees." And that presents an opportunity for middling: "You can make one bet early [on the Yankees] and one bet late [on the opposing team] when, at the last minute, all the square action goes to New York." Finally, he adds, if you want to get serious about baseball, focus on one particular ball club, learn all the nuances and subtleties, and make sure you don't fall in love with your chosen team. "If half your total number of bets are not on the other side, you're probably doing something wrong."

The beauty of following a single team is that it allows you to proceed with a fair bit of obsessiveness that should result in your seeing the numbers below the numbers. For instance, if a pitcher allows the bases to get loaded and a sharp grounder is hit to the shortstop who manages to orchestrate a double play, well, that's great, but it isn't exactly a vote of confidence for the pitcher—since that same shot to the shortstop could have easily resulted in a couple of runs scoring. Never mind that the pitcher's earned run average and numerically driven stats will make everything look duckier than it really is. Or, as Fezzik puts it, "Spot pitchers whose ERAs are not in line with the way they throw, and you can get yourself into great shape."

Fezzik's success in gambling on baseball comes from the emphasis he puts on betting—that is, finding the best prices, seeking out niches for prop bets, snagging opportunities to middle a game—rather than handicapping. On the opposite end of the spectrum is Michael Murray. A Kansas-based bettor and author of Betting Baseball, Murray has tricked out an Excel spreadsheet program for calculating baseball. "I'm better at predicting how pitchers will throw than the bookies are," brags Murray, who placed 1,000 over/under bets last season. "Instead of counting the number of runs, I take into account strikeouts and walks and home runs, and use that information to arrive at a sort of expected earned run average. Most bettors don't do it. So most bookies don't do it, either. If they go too far out of line, they'll get too much action on one side and not enough on the other."

Similar to Fezzik, who has found his edge in making proposition bets, Murray focuses on winning bets against bookies who take action on the outcomes of the first five innings. "There are teams that are really piss-poor after five innings," says Murray, explaining that their best playing takes place before the game's midway point. "The Royals and Cubbies blow a lot of leads because of their lousy bullpens. But if you bet them for the beginning of the game, and they've got good starting pitchers, you get good value."

But aren't the bookies taking all of this into account as well? "Sometimes," acknowledges Murray, who recently got 200-to-1 odds on the Oakland A's winning the World Series (though it's obviously a long shot, he believes that their actual chances are 20-to-1). "But they don't spend as much time on the first five-inning lines as they do on the entire game."

Tougher than getting down bets and making lines is the sheer money- and information-management aspects of baseball. Many games are played each day of the season, and the heavy schedule necessitates careful attention to ever-fluctuating statistics, lineups and situational changes, such as the weather and the stadium. For instance, as Murray points out, some ballparks tend to be the homes of high scores. Coors Field, in Denver, inflates league scoring by 40 percent, he says; Kauffman Stadium in Kansas City deflates it by 11 percent. And the long season, with inexplicable streaks and slumps and upsets, can wreak havoc on a gambler's bankroll. "Go 5-and-6 one week in football, and you're fine," says Murray. "Do it every day for a week in baseball, and you have big problems."

If anyone can ride out the bad streaks of baseball, it's a professional blackjack player, the kind of gambler who's accustomed to running bad night after night but has enough faith in his card-counting system to recognize that, ultimately, he'll wind up with a profit. Such had been the case for a successful under-the-radar counter who's known by several names to bosses in the blackjack pits. For the purposes of this story, he asks to be called Baseball John (it's how sports book managers referred to him when he'd suddenly pop up at the start of the season and make massive bets). John says that he managed to win $700,000 over nine years of betting baseball.

His interest in baseball began when he discovered that a rogue computer programmer of his acquaintance—a guy who was famous for implanting tiny computer units in shoes for professional blackjack players—had designed a baseball-betting program for two top poker pros. Through a series of happy coincidences, John happened to receive a firsthand look at how the programmer devised his baseball lines; then John decided to sit down and do it himself. "You hear people say that the pitcher is 90 percent of the game," he explains over a lavish, comped dinner at Mix, Alaine Ducasse's chic new restaurant on an upper floor of The Hotel in Mandalay Bay in Las Vegas. "To me and the programmer, a guy who's a certifiable genius, pitching and hitting are two sides of the same coin. So the starting pitcher is less than 50 percent of the overall equation. Most people underestimate hitting and overestimate starting pitchers. The other thing is knowing how much unpredictability is involved. Coming from blackjack, I knew better than trying to handicap a winner. I handicapped the line. If I had an underdog at plus $1.30, but the line being offered was plus $1.40, I would happily bet the 'dog and know that I'd win enough of those games to turn a profit. I loved false favorites."

In doing his handicapping, which was sheer pleasure for the mathematically oriented John, he thought about the pennies that each aspect of a game would be worth for a team. For example, he'd look at the home-field advantage, giving extra credit to teams with artificial turf and indoor stadiums, which could total 20 cents. Next would come batting and pitching. "You look at two players, maybe Mike Mussina versus Pedro Martinez, and figure out who's worth what against the other," explains John. "Maybe Martinez would be 25 cents better. Then I would look at the relief pitchers. On average, one-third of the innings would be pitched by relievers, but you don't want to factor in the relievers as one-third of your pitching decision because it's such an unknown. You overweight the starting pitcher," he says, adding, "as for fielding, I tried to keep it simple and focused on errors. Finally, I'd bet against positive streaks [that is, teams that were winning multiple games in a row] because they get over-bet, and you can get good prices by going in the opposite direction of everyone else."

But getting to that point—and making his 700 grand—was hardly simple. Unlike his computer-programming friend, John did his stat keeping with pencil and paper, partly because he's a bit of a Luddite, partly because he saw some advantages in operating the old-fashioned way. "There were things that I would do better than the computer could," says John. "The computer couldn't think. I would sweat every game and develop a feel for the players. Then that would be factored in along with everything else." One disadvantage of the flesh-and-blood approach is the man-hours required to do all the calculating, which made it impossible for John to handicap each game. Ever the advantage player, he found a relatively simple solution: "I only handicapped teams that had been underrated or overrated by the line makers"—and, of course, those teams changed day to day.

Though John admits that he's never been any kind of an athlete and isn't even much of a sports fan, his adventures in baseball were a lot of fun, an interesting challenge and, of course, profitable. Ironically, considering its lackluster popularity among most gamblers, baseball stands as the only sport he'd be interested in betting. "I prefer a money line to a point spread and would never like the idea of betting a favorite at football or basketball," he says. "In that instance, you're dealing with a team and a coach that are not trying to cover the spread. They're trying to win the game. They want something different than I do. So why should I bet on them?"

For all of that, however, baseball is a tough nut to crack—so much so that John's given up on betting the sport altogether—at least for the foreseeable future. Ultimately, he's decided that it's less risky to devote all his time to blackjack. And he's not alone. Even some of Vegas's most venerable, long-term successful gamblers find it difficult to turn a profit by betting on runs and hits and pop flies. "I don't like to lay $1.60 [that is, put up $1.60 to win $1], and that hurts me in baseball," admits veteran sports bettor Lem Banker. "Nobody wants to lay a price. We all prefer betting on a live underdog [that is, taking the worst team and getting points, as in basketball or football]. The smartest guys I know—including the legendary bookmaker Bob Martin—went broke betting baseball."

Yet, like a lot of other sharp sports bettors in town, Banker continues the uphill struggle of trying to beat the game. How come? He shrugs and acknowledges the difficulty of ignoring a put-your-money-where-your-mouth-is challenge. "What else are you gonna do?" asks the action-hungry Banker. "It's a long season. But I know a lot of guys who can't wait till July or August, when exhibition football kicks in."

Michael Kaplan is Cigar Aficionado's gambling columnist.