Here's a the recent Reds front office employee with the Godfather character they most resemble (not looks wise). I think there are a lot of good comparisons and thought of a lot of valid ones, but I'll start with one and see what everyone else is thinking.

Fredo Corleone = Dan O'Brien

Both caused so much unintentional comedy in their roles the comparison is perfect. I could just see him crying to Castellini "The Pirates told me there was something in it for me." Next?