The Undoing Project: A Friendship that Changed the World(4)

His interest in sports and statistics had led him, at the age of sixteen, to pick up a book called The Bill James Historical Baseball Abstract. Bill James was then busy popularizing an approach, rooted in statistical reasoning, to thinking about baseball. With some help from the Oakland Athletics, that approach would trigger a revolution that ended with nerds running, or helping to run, virtually every team in Major League Baseball. In 1988, when he stumbled upon James’s book in a Barnes & Noble, Morey had no way of knowing that people with a gift for using numbers to predict things would overrun professional sports management and everyplace else high-stakes decisions were being made—or that basketball would be, in effect, waiting for him to grow up. He simply suspected that the established experts maybe didn’t know as much as everyone thought they did.

That particular suspicion had been born the year before, 1987, after Sports Illustrated splashed his favorite baseball team, the Cleveland Indians, on its cover and picked them to win the World Series. “I was like, ‘This Is It!!!! The Indians have sucked for years. Now we’re going to win the World Series!’” The Indians finished that season with the worst record in the major leagues: How did that happen? “The guys they had said were going to be so good were so bad,” recalled Morey. “And that was the moment when I thought: Maybe the experts don’t know what they’re talking about.”

Then he discovered Bill James and decided that, like Bill James, he might use numbers to make better predictions than the experts. If he could predict the future performance of professional athletes, he could build winning sports teams, and if he could build winning sports teams . . . well, that’s where Daryl Morey’s mind came to rest. All he wanted to do in life was to build winning sports teams. The question was: Who’d let him do it? In college he’d sent dozens of letters to professional sports franchises in the hope of being offered some menial job. He received not a single reply. “I didn’t have, like, any way to penetrate organized sports,” he said. “So I decided at that point that I had to be rich. If I was rich I could just buy a team and run it.”

His parents were middle-class midwesterners. He didn’t even know any rich people. He was also a distinctly unmotivated student at Northwestern University. He nevertheless set out to make enough money to buy a professional sports team, so that he might make the decisions about who would be on it. “Every week he’d take a sheet of paper and write on top, ‘My Goals,’” recalls his then-girlfriend, Ellen, now his wife. “The biggest life goal was, ‘I’m going to someday own a professional sports team.’” “I went to business school,” said Morey, “because I thought that’s where you had to go if you wanted to get rich.” Upon leaving business school, in 2000, he interviewed with consulting firms until he found one that got paid in the shares of the companies it advised. The firm was advising Internet companies during the Internet bubble: That sounded, at the time, like a way to get rich quick. Then the bubble burst and all the shares were worthless. “It turns out it was the worst decision ever,” said Morey.

From his stint as a consultant he learned something valuable, however. It seemed to him that a big part of a consultant’s job was to feign total certainty about uncertain things. In a job interview with McKinsey, they told him that he was not certain enough in his opinions. “And I said it was because I wasn’t certain. And they said, ‘We’re billing clients five hundred grand a year, so you have to be sure of what you are saying.’” The consulting firm that eventually hired him was forever asking him to exhibit confidence when, in his view, confidence was a sign of fraudulence. They’d asked him to forecast the price of oil for clients, for instance. “And then we would go to our clients and tell them we could predict the price of oil. No one can predict the price of oil. It was basically nonsense.”

A lot of what people did and said when they “predicted” things, Morey now realized, was phony: pretending to know things rather than actually knowing things. There were a great many interesting questions in the world to which the only honest answer was, “It’s impossible to know for sure.” “What will the price of oil be in ten years?” was such a question. That didn’t mean you gave up trying to find an answer; you just couched that answer in probabilistic terms.

Later, when basketball scouts came to him looking for jobs, the trait he looked for was some awareness that they were seeking answers to questions with no certain answers—that they were inherently fallible. “I always ask them, ‘Who did you miss?’” he said. Which future superstar had they written off, or which future bust had they fallen in love with? “If they don’t give me a good one, I’m like, ‘Fuck ’em.’”

By a stroke of luck, the consulting firm Morey worked for was asked to perform some analysis for a group trying to buy the Boston Red Sox. When that group failed in its bid to buy a professional baseball team, it went out and bought a professional basketball team, the Boston Celtics. In 2001 they asked Morey to quit his job consulting and come to work for the Celtics, where “they gave me the most difficult problems to figure out.” He helped hire new management, then helped to figure out how to price tickets, and, finally, inevitably, was asked to work on the problem of whom to select in the NBA draft. “How will that nineteen-year-old perform in the NBA?” was like “Where will the price of oil be in ten years?” A perfect answer didn’t exist, but statistics could get you to some answer that was at least a bit better than simply guessing.