Theo's very funny. Obviously, we see and hear him alot on TV and radio here in Boston. In interviews he's fast on his feet (if that makes sense) quick with a snappy response to sarcastic, or joking questions. His delivery is pretty dead-pan too. I could see how players would like a guy like Theo as a GM, in many ways he talks and acts like a player would.
In the same vein, manager Terry Francona, while he comes off soft-spoken and humble, is good for a clever line or two when he sits down for an interview.
You probably heard a couple of weeks ago, he was doing a phoner from his car in florida with the mid-day Boston radio guys when his car got rear-ended pretty good in the middle of the interview. He told the hosts what happened and explained he'd have to end to interview to go deal with the accident. But before he signed off, he dead-panned (jokingly) "and wouldn't you know it -- the car's got a Yankees licence plate..."
That's pretty darned good... to come up with a line like that moments after someone smashes into your car....