Wright Thompson, ESPN The Magazine:
Epstein knows how others see him, and he's self-aware enough to both understand his reputation and mock it. His friends are always baffled at his image as a cold exploiter of markets and inferior systems. One night this summer, the owner of the team, Tom Ricketts, held court at a charity boxing match and explained that few people are as different from their public narrative as Theo: He gets painted as a quant, while his attachment to baseball is actually deeply emotional. When the team is on the road, or playing a home night game, he sometimes brings his lunch to Wrigley just to eat in the empty bleachers. He loves how the ivy turns bright red at the end of October, which most fans don't know because the team has never played in Wrigley that late in the year. He loves the changing seasons, and quoting both Dazed and Confused and Othello, and reading the Russian writers whose dramas play out inside the psyches of their characters. He read Crime and Punishment once in high school and again in college -- and he feels that those kinds of internal struggles are authentic to his own, which isn't against his environment (upper-class Jewish) or his station (intellectual Brookline, Massachusetts) but rather against the things inside his own head, cycles of guilt, passion and redemption. The main battle he fights is against himself. "If I let my brain follow its path unfettered, it would be kinda ugly," he says. "I learned simple mental health things: self-talk, breathing."
His public mission is simple and well-known: Break another curse. But privately, he came to the Cubs for something personal and nearly as important, which he doesn't talk about. In Boston, he lost control of his obsession, the belief that a collective of people can do one thing better than it's ever been done. At the very end, he became a shell of the person who fell in love with the game, stress turning into physical symptoms, like a neck that hurt so bad he couldn't turn his head more than a few degrees. His friends saw how the job changed his face. That's what they talk about when describing the cost Theo paid, how he looked different. "There is definitely at times a hollowness to him that drives him," says one of his old Red Sox co-workers. "There's some black pockets with him that are just dark. When he's down, he goes to extremes."
During the Red Sox's famous chicken-and-beer collapse, he couldn't sleep. Staff members made jokes about waiting on the sun to rise, mocking their own despair. But on a few bad nights, when things felt bleak, Theo would wander the internet, lingering on macabre things like air traffic controller recordings from plane crashes. He knew he needed to leave Boston, to start fresh, no matter how the collapse made the exit look or feel. "I hated I was seen as running from the collapse," he says, "but I guess on some level, I was running from something."
He arrived in Chicago to rebuild a franchise -- and part of himself too.