I grew up in Massachusetts, and was a Bruins fan. I took a liking to the Senators because I thought Alexandre Daigle was the next big thing....boy were we wrong. Anyway, I liked the Senators in spite of them being horrible because the B's would usually school them pretty well, so it was like a 'yes, Ottawa's coming to town'. As they started developing more talent, I became more of a fan. I've been a Daniel Alfredsson fan since 1995, when he broke into the league.
Since I grew up in Mass, the Red Sox were, and no matter how much they break my heart or piss me off at times, will always be my favorite team. But, I wanted the Phillies to win the 1993 World Series, and they had my favorite player on their team then (Curt Schilling).