Theo Epstein has been in the same position the Boston Red Sox now face on three separate occasions, and he failed to reach the goal all three times — but you can file this one under “good problems to have.”
The Chicago Cubs president of baseball operations has overseen three different World Series championship teams, but he has yet to orchestrate a repeat title season. Epstein is credited with building the 2004 and 2007 Boston Red Sox teams that won it all before leading the Cubs to their long-awaited glory in 2016.
On all three occasions, Epstein’s clubs were capable of repeating, but all three fell short of their ultimate goal the following season. The Epstein-less Red Sox now will try to become the first team since the 2000 New York Yankees to repeat as champions, and Epstein knows firsthand how difficult that task will be for Boston.
“Obviously ’16 to ’17 is freshest in my mind but there can be this sense that if you’re not careful, that when you report to spring training after winning the World Series, it feels like you’ve just climbed Mt. Everest, and what feels like just a few weeks later, even though it’s a few months later, you’re asked to do it again,” Epstein told the Boston Herald.
“How do you take that first step? You just got to the mountain top. I’ve had players admit this to me, that it can be disorienting. There’s a risk of not being fully bought in to the daily routine and the daily grind in the face of having just been so high on the mountain and then having to take the first step of the journey again.”
Epstein was careful not to overstep his boundaries and make any assumptions about the Red Sox from afar, but he shed some light on some of the mental challenges that come with gearing back up after having such recent success.
“There’s always a risk of a sense of entitlement that creeps in,” Epstein explained to the Herald. “Players and front-office members, everyone goes home for the winter and after you’re all together for the whole postseason, you go home and no matter how selfless or benevolent or altruistic you are, it always reaches a point where you look in the mirror and say ‘Well, I was a pretty big part of that — what about me?’ Sometimes your agent is telling you how much you contributed and how much that’s worth — it can risk that great team connection that brings you the success in the first place, and that can be jeopardized with all the aftermath that comes with winning a World Series.”
That Epstein, who was able to help restore glory to two long-suffering franchises, hasn’t been able to crack the code really reinforces how difficult it is to repeat as champions. But the Red Sox are hoping they can push through where Epstein’s teams have fallen just short.
