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The Good Life

Wagering 1-on-1 Sports

Sports bettors find an edge when athletes compete as individuals rather than teams
| By Jeff Williams | From Havana—The Insider's Guide, November/December 2011
Wagering 1-on-1 Sports
Illustration/Ed Fotheringham

If it’s golf season on a Tuesday afternoon in Las Vegas, then it is a lock that Bill Krackomberger will be cruising the casinos and placing bets on matchups for the coming week’s tournament. After getting the go-ahead from a partner who researches 18-hole pairings, Krackomberger leaves his Las Vegas high-rise and hits the sports-books by mid afternoon. List in hand, he looks for what he perceives to be miscalculations on the parts of the bookmakers. While the rest of the world aims to bet on that night’s Major League Baseball, Krackomberger is focusing on one-to-one matchups—sports that pit individuals against one another rather than entire teams.

Krackomberger has no qualms about wagering on teams, but astute gamblers know that betting on athletes in individual sports can have certain advantages. For starters, they can be more accurately handicapped. When you have one player going up against another, there is less likelihood that outside elements—say, friction between a coach and a quarterback—will enter into the mix and sour an otherwise well-considered opinion. Additionally, as one bettor puts it, “Players in one-to-one sports tend to play truer to form.” In other words, there are fewer upsets and things tend to go the way that you think they will.

During a good day, Krackomberger will place anywhere from five to eight different bets. Or else, when the situation warrants it, he bets for or against one key golfer in every possible scenario. “If we hear that he’s on his game, or the opposite, we wager in the appropriate direction,” says Krackomberger. In time for a late dinner, he gets down all the action he needs for the coming week’s rounds of golf. “Then it’s just a matter of sitting back, waiting until Sunday night and seeing how we have done.”

Favorite sports for the one-on-one professionals include golf, tennis, NASCAR and boxing. Though the latter of these has become increasingly difficult to beat, with long odds for favorites that are often tough to overcome, the simple act of remaining focused can often pay dividends. Billy Baxter, a veteran sports bettor who’s managed champion fighters and knows the boxing world as well as any gambler, discovered that he was on the wrong side of a bet just by looking at a contender before the weigh-in and after.

It happened in 2008 when Oscar De La Hoya fought Manny Pacquiao. At the weigh-in, where De La Hoya tipped the scale at 147 pounds, Baxter believed that he looked good. Considering that he’d have a day to bulk up, says Baxter, “I figured that he’d come back at 160. But when I saw him on the night of the fight. I immediately got off of my bet. He came back at 147 and looked like a shell of himself. I never saw anything like it.”

It was a bout in which De La Hoya got famously creamed to the point that the match served as his swan song from the sport. But if the fighter got massacred, Baxter managed to leave the MGM Grand, where the bout took place, unscathed and with his bankroll pretty much intact. He reversed his bets, by wagering in the opposite direction, before the first punch was thrown.

When Bill Krackomberger and his partner, who goes by the single moniker of Sam, tell me that they bet NASCAR, I look at them with disbelief. They’re a couple of action guys from South Jersey, and stock car racing just does not seem to be in their DNA. What dominates their genes, however, is winning money through gambling wherever they can find an edge. A good sign that there are soft lines to be taken advantage of in NASCAR? “Las Vegas usually doesn’t put up player vs. player in NASCAR because the casinos were getting beaten up,” says Krackomberger over a fancy Chinese dinner at Blossom, a stylish restaurant inside Aria at City Center. “They only do it when the race is taking place in Vegas.”

Decisions for Krackomberger and company are informed via a combination of analysis, inside information and looking for more than what is readily available to the general public on the Internet. “We’ve been involved with a guy who knows everything about pit crews and about which cars are training well,” Krackomberger says. “For example, it’s real important to have a guy on the track, timing cars going around before the race, on hot tires.” The term “hot tires” refers to what happens after a stock car has completed eight or 10 laps through the course of a practice session.

According to Krackomberger, the hot-tire times are much more telling than the widely disseminated cold-tire times that are used to determine pole positions.

But sometimes, even all the information in the world will not be enough to overcome the flukiest of freak incidents. He recalls a race from some years back in which he and his partner had handicapped driver Sterling Marlin as a 10-to-1 shot to win the race and the sports books had him at 40-to-1. It was a serious miscalculation and Krackomberger took advantage.

“I bet $500 to win $20,000,” he remembers. “We did everything right: we came up with the right number, we found the right price, we got our bet down and everything was going the way it should have. Sterling was winning the whole race. He was ahead of everyone with just half a lap to go. Then we saw his car starting to shake. He ran out of gas just before the finish line. All he needed was fumes for us to win the 20 grand! That one hurt.”

However, that’s the less likely outcome. Krackomberger opens up his laptop, logs onto a betting account and scrolls down the screen, exposing one payoff after the other, showing me that incidents like the Sterling fiasco are indeed rare. “If I told you our win percentage at NASCAR no one would believe it,” he says. “So I’m not going to tell you.”

A bit less esoteric and, therefore, more prevalent in the Las Vegas sports-books are golf matchups. In these, you bet on an individual golfer to beat another golfer. Or else you can take a do-it-yourself approach. Baxter recalls going out on the PGA tour with other gamblers and literally betting on the entire field, matching up one golfer over the next. “When you get down to the 60th or 65th player, that’s where the real skill level comes in,” he says. “You need to have an opinion on golfers that a lot of people don’t know very much about.”

Along the way, Baxter also gleaned some concrete insights about betting golf matchups in general. One of them is to keep an eye on how a player finishes the previous day’s round. “It matters what they shoot on the back nine,” says Baxter. “Two guys can both have a score of 72, but if one guy finished with a 39 and the other guy finished with a 32, it can mean something. Maybe the guy who shot 32 on the back found something that works for him and the guy with the 39 is all screwed up in the brain. Your mental state of mind when you come off the golf course is very important.”

Golf also happens to be a sport that lends itself well to analysis. Sam feeds loads of information into a computer and has a software program that does the heavy lifting. He includes course history, form, whether the golfer is improving or declining or staying the same, who he’s matched up against and how his style lends itself to a particular type of course. Here’s how critical that last element can be. “The No. 1 player in the world is Luke Donald, and I don’t ever see him winning a Masters,” says Alf Musketa, a sports bettor who favors head-to-head wagering. “He doesn’t hit the ball long enough from the tee. He’s always going to be matched up against somebody at the sports-book—and if he’s matched up against the right guy, on the right course, I’ll take the other guy.”

It also pays to look for people who are suddenly underperforming or who have patterns of underperforming during pertinent conditions. Musketa has done well this season betting against Ernie Els, Tiger Woods, Padraig Harrington and Anthony Kim. “It’s easy to play lousy golf,” he says, adding that it’s worthwhile to figure out which golfers lose their drive if they shoot badly on day one or three. “When I find a guy who’s struggling, I look for opportunities that will allow me to go against him in his next match.”

Having a reliable contact with inside information doesn’t hurt either. Working with a partner in Myrtle Beach, South Carolina, Krackomberger got a report from the massage table of Greg Norman. “I heard that he had just gotten massaged, he hurt his right ankle, and that he would play a couple of holes in order to satisfy a sponsor,” remembers Krackomberger. “I ran around town, looking for every matchup possible against Greg Norman. I got down a high five-figure sum all told. Norman shot something like a 92 and barely finished the round. That illustrates the power of information.” Half-laughing, he adds, “I’d say that we had a one-million percent edge on that bet.”

Nice as it may be to have inside information, it definitely is not integral and, in some cases, the information doesn’t even need to be all that inside. Recently, Billy Baxter happened to be watching tennis on television and he heard something that should have seemed like solid-gold to any serious sports bettor. “Two weeks ago I bet against Novak Djokovic,” recounts Baxter. “I was listening to John McEnroe and those guys, and they were talking about all the hard matches that Djokovic had. They were almost predicting that he would not be able to finish this upcoming match against Andy Murray. I took Murray at 3-to-1 and couldn’t believe that the price was that high, especially after what was being said about Djokovic.” The commentators were right. “He just quit in the middle of the second set!”

Admittedly, that’s the kind of circumstantial information that no sports bettor can make a living off of. It just isn’t put out there frequently enough to amount to a decent earn. But if tennis is your game, there are other opportunities for finding head-to-head advantages. Begin by factoring in the standard issues: whether or not a player is successful on a particular surface, if he does better during the day or at night, if he’s playing without a break and how that might impact his competitiveness, the history of players against one another and the ways in which their styles mesh. Then, beyond that, there are other, less obvious, elements to consider.

For instance, keep in mind whether or not a player puts in a full effort when a match is less than critical. Also look at the reason why a superstar is playing a particular match. “The best plays in tennis are the big underdogs against a disinterested favorite,” says Sam. “Serena Williams playing a mid-level female is an example of that, especially if she hasn’t played for four months and is using the tournament as a tune-up. Beyond the fact that she’s always overrated [and, thus, overpriced] by the books, for her opponent it’s the match of a lifetime while the Williams sister doesn’t really care.”

Considering his approach to successfully betting on head-to-head outcomes, Sam likens it to beating the stock market by “becoming fully aware of, say, a small niche in consumer goods.” Backing up the claim, he has bet heavily (and strategically) on the outcomes of events that range from presidential elections to the Academy Awards to “American Idol.”

“I bet $10,000 on ‘American Idol,’ ” says Sam, “and I had a good year with that TV show.” Other unlikely spots where gamblers can find advantages are with sports that remain obscure by American standards. Alf Musketa has made himself an expert at darts and snooker, which present good opportunities at low stakes. A gambler who posts online as Goats has focused on NFL proposition bets, wagering on whether one quarterback will throw for more yardage than another one or if a running back will out-rush his counterpart on the opposing team.

Goats uses fantasy football information as a base and then builds in his own opinions and stats before putting up money. “One thing you can look for are large-spread games,” he advises. “If the line is seven or higher, you expect that the underdog will need to throw more and run less in order to catch up. And the big favorite, if they’re up, will probably hand-off more in order to run out the clock. You’ll be looking to play the quarterback in a matchup if his team is a major dog.”

Whatever corner of head-to-head betting you decide to focus on, be cognizant that it takes diligence, studying the players and reaching a strong opinion on one end of it or the other. On the upside, though, the bookies and oddsmakers rarely have time to thoroughly investigate small-market bets that generate way less revenue than mainstream NFL or NBA wagering. And sometimes the most obvious things are overlooked.

In 2008, during the Scottish Open, for example, Musketa happened to catch a Tweet from John Daly. “He wrote, ‘I’ll be lucky if I can tee it up on Thursday and can barely get through the ball,’ ” remembers Musketa. “I found only one matchup for Daly, against Colin Montgomerie, and I played that until the casinos took it down. Daly played nine holes before quitting and it made me a winner no matter what Montgomerie shot. You don’t get information like that on an NFL game.” Savoring the easy money, Musketa smiles and says, “I keep a file with all the golfers’ Tweets. I’ve discovered that you never know what they’ll say on Twitter”—or how handsomely it might pay off.

Michael Kaplan is a
Cigar Aficionado contributing editor.


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