Epstein, then the Red Sox general manager, traded for Schilling in 2004, giving Boston the ace it needed to break an 86-year drought and win the World Series. Now Epstein has begun a new challenge -- deliver a World Series to the Cubs, who are stuck in a 103-year drought.
Schilling, now an ESPN analyst, believes the Cubs picked the right man for the job.
"He understands the human element to this. A lot of what I learned from and about Theo I've taken into my company and tried to help my company grow. Theo gets it, and it's not lost on the people who played for him. He's the only general manager I ever played around who fit into the clubhouse. That's a very dangerous thing for general managers, especially if they don't fit. He was always welcome. He's a very smart guy."
In their first Cubs offseason, Epstein and general manager Jed Hoyer have focused on moves for younger players coming off down years at an affordable price rather than landing a big-ticket free agent such as Prince Fielder.
Rebuilding with young major league talent and retooling the minor league system likely won't lead to immediate success, but Schilling said it will come.
"I think you're in for an incredibly good run over the next couple of years. It's going to take some time, and he's not going to make perfect decisions every time as well, but this guy is going to build a player development powerhouse. That's where everything starts and finishes these days."