Theo Epstein Used to Follow Strangers Home and Watch Them

In a long profile with ESPN’s Wright Thompson, Chicago Cubs general manager Theo Epstein reveals, among other things, the struggle he had with fame when he became GM of the Boston Red Sox at age 28.

Epstein was an introverted stats guy who got famous overnight. As he grappled with the loss of his own anonymity, he began trying to find it vicariously by following home strangers and watching them.

"The morning Epstein became the GM, he walked outside his condo near Fenway and found camera crews waiting, and they followed him to work as he reminded himself not to trip, concentrating on the steps. Even now in Chicago, he often tugs at the bill of his cap, a nervous tick left over from when he became a public figure overnight. “I was emotionally 16 when I was 28 and got the job,” he says. “I was so introverted. I used to follow people home. I just like being anonymous so much that I would follow people home because they didn’t know who I was and I could watch them. I know how that sounds. I could not exist but observe. I could put a hat on and follow them.”I was so introverted. I used to follow people home. I just like being anonymous so much that I would follow people home because they didn’t know who I was and I could watch them. I know how that sounds. I could not exist but observe. I could put a hat on and follow them.”"

The story functions as sort of a psychological profile of one of the most curious executives in professional sports. It paints a picture of a jocular wiz kid who works too hard and got really successful, really fast.

So successful he needed to call Bill Belichick for advice on handling it.

"“You’re f***ed,” Belichick told him."

It’s worth a read.