I hope it’s OK if I call you by your first name. I actually don’t even know if it’s short for Theodore or something else. For all I know, you may not even like to be called that. If there’s something else you’d rather go by, please accept my apologies.
I must tell you that I’m very excited that you’re coming to Chicago. I have family in Boston, and the World Series titles you brought to them meant a great deal. They also meant a great deal to you, I’m sure. Ending the long championship drought for your hometown team must have been an unbelievable feeling. And then to follow it up with another title must have been even better. Kudos to you for such a great accomplishment.
I know that leaving Boston will be hard for you. But if there was ever a bigger challenge than winning in Boston, winning with the Cubs is it. It’s been said many times that whoever wins here in Chicago will be remembered forever, and I’m glad to see that you’re willing to accept that mantle. You’ve already proven something to me (and hopefully to others) just by taking that step.
I’m writing this because I have followed this team for as long as I can remember, stretching all the way back to the mid 1970s. The Cubs were my team then, and they’ll always be my team in the future.
Unfortunately, we Cubs fans are twisted in some sense. It’s like we’ve been locked away in a dungeon for a very long time, and given just enough to survive, but never enough to really flourish. We’ve heard about success, and have even watched while others have tasted it, but it’s never been within our grasp. Hopefully we’ll know that feeling someday soon.
Please accept my best wishes for your success in Chicago.
Most sincerely yours,
UPDATE: Theo Epstein stepped down from his role with the Chicgo Cubs today, nine years and one month after I wrote this letter. The success he had during his time with the Cubs is something I’ll always remember fondly. Thanks for the memories, Theo!