Tom Tippett’s love of sports data began at age seven, when his mom bought him a stat-tracking book so that he could follow numbers for NHL players. But as much as the Toronto native loved hockey, baseball offered an even greater data set—perfect for the burgeoning math whiz. “I was interested in sabermetrics before it was even a word,” says Tippett (MBA 1985).

Today, it’s a cultural phenomenon, thanks in no small part to Brad Pitt and the Oscar-nominated 2011 adaption of Michael Lewis’s Moneyball. But well before baseball stats went Hollywood, Tippett was quietly turning industry heads with something decidedly less flashy: a graphics-light, stat-heavy computer baseball simulation game called Diamond Mind Baseball. Launched commercially in 1987, the game puts players in the manager’s seat, letting them make tactical decisions against a mathematical model that determines outcomes based on everything from how a batter has historically fared against a certain pitcher to the ballpark where the game is played.

As the sport began to increasingly rely on the kind of data projections that drove his game, the Boston Red Sox brought on Tippett as a consultant in 2003, eventually promoting him to director of baseball information services; last year he was named senior baseball analyst. Tippett sold his simulation game in 2006 but credits it with providing lasting insight. “It was the perfect marriage of sports and numbers,” he says. “It forced me to study baseball at a very detailed level. I had to learn as much as I could, such as studying how managers made decisions. I really dove deep into the strategy of baseball.”

And now that stats-driven scouting is the norm, those dives must go even deeper. Every pitch thrown in the big leagues today is broken down not only by velocity, type, and location but also by trajectory—a far cry from the basic ball or strike tallies collected 15 years ago. According to Tippett, some of the most revolutionary analytical tools developed in recent years are motion-capturing systems that can track player and ball movement, revealing, for example, whether an outfielder gets an early jump on a ball hit his way.

As the Red Sox look to bounce back after a disappointing 71–91 season, it’s imperative for the franchise to stay at the cutting edge of the data wars. For Tippett, that means continuing to add to his arsenal: a massive database of baseball metrics and minutiae that he and the team have been building for the last decade. “There’s a clear direction for the future at the moment,” says Tippett, pointing to pioneering new initiatives like Major League Baseball’s Statcast (above), which offers statistical insights into every play—from the launch angle of a batted ball to a fielder’s acceleration. “With every revolution, there is a new data stream to learn from.”

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