March Madness -- it's a spring ritual at offices across the nation. From CEO to secretary, from mailroom to corner office, just about everybody throws their five bucks into a pool for the NCAA Men's Basketball Tournament, in hopes of winning bragging rights and a pile of cash to finance that celebratory happy hour. Problem is, it could also land you in jail.

Of course, you're about as likely to be arrested for jaywalking. According to a survey by, 57% of workers across the U.S. take part in NCAA pools, ranking just behind the Super Bowl in popularity for office betting. Pools on baby births follow at 19%, and the Academy Awards -- often dubbed the "female Super Bowl" in betting circles -- come in at 13%.

And while these "crime waves" sweep the nation every time the playoffs roll around or George Clooney pockets a golden statuette, the feds aren't all that interested in locking up the guy who picked North Carolina last year. "If somebody brought me the case, I wouldn't touch it," says one East Coast prosecutor, who asked not to be identified, for obvious reasons.

Technically, it is illegal to "place [or accept] a bet or wager, gamble or make books or pools on the result of any athletic contest." This means that NCAA tourney pools, along with wagers on "polo games" and "trotting or running races of horses" are misdemeanors that could result in 180 days in jail or a $1,000 fine, according to local criminal code. But, according to the prosecutor, nobody has ever come forward with a case. "I don't know who would complain and say, 'My officemates have a football pool going and I think it's illegal and you should prosecute this."

Most employers don't seem particularly concerned, either. Officially or unofficially, many sponsor their own pools -- especially in smaller companies -- and according to a survey by the Society of Human Resource Managers, only 23% of workplaces have a written policy forbidding such gambling in the workplace.

So if you do enter an "illegal" pool this year, how can you maximize your chances of winning, even if you don't know slam dunk from jump shot? For starters, don't waste time reading every sports column, surfing college basketball blogs, or listening to sports talk radio for tips on "who's hot." As it turns out, sports experts tend to do significantly worse in pools than those mostly picking at random.

"I don't know very much about basketball," says Vicki Morwitz, a New York University marketing professor who, after winning her own office pool, began a study as to why non-hoops fans always seem to edge out the sports nuts.

After assigning basketball-knowledge quizzes to pool participants, she found that "experts have a lot of very specific knowledge about players and teams, and they tend to overrate that knowledge." Those with only moderate sports knowledge were able to pick winners just under 50% of the time, while the most knowledgeable sports fans averaged in the low 30% range -- decent odds for a three-point shooter on the court, but not so great for winning the office pool. The most die-hard sports fans "are overconfident," Morwitz says. Her pick for this year? "I can't answer that one," she says coyly.

If you're looking for a real advantage -- one with some cold, hard calculus behind it --there's a better option than trying to unlearn your basketball knowledge. Edward Kaplan, a Yale School of Management professor, is an expert in operations systems, probability modeling, and mathematics. As an academic, Kaplan models the spread of AIDS and other diseases for public policy analysis, but in his spare time, set out to find a way to win his NCAA office pool. "We used to enter these things for fun, and always for bragging rights, [but] we would always lose," he says. "We realized we were going about it randomly and not systematically."

So Kaplan and a colleague hired a research assistant to pull basketball data from sports gurus' ratings, regular-season records, and the Rankings Percentage Index (RPI) to create a complex web of relationships between teams, evaluate their strengths, and find a way to optimize points for a tourney bracket. Recently, he's also been using Las Vegas odds to incorporate late-breaking information.

Kaplan calls his system "fairly complicated," and says that with the opening-round play-in game, there are an estimated 18,000,000,000,000,000,000 (that's 18 billion billion, as mathematicians say) options that his calculations examine.

While it may be difficult to replicate Kaplan's math at home (you can go to and try his interactive calculator, however) he recommends two strategies to maximize your chances of getting those office bragging rights. First, he says, start backwards, picking the tournament's overall winner to start, then the Final Four, and so on. The concept behind his method is to pick winners based on their comparison to the rest of the field, rather than just the individual games in which they play. Second, he says, make sure to differentiate your picks from what you think other people will choose -- picking lower seeds, for example, lessens your chances of having to split the money. So who's going to win the tourney? "UConn," Kaplan says. Of course, it's anyone's guess.