Being I grew up in Va/NC my Boston loyalty only goes to the Celtics and the Red Sox. My favorite hockey team is the Bruins but I have to admit to hardly watching hockey. With football, I've been cursed to be a Redskins fan which for the past 20 years has totally sucked. That being said, I am a die-hard Celtics and Red Sox fan. My dad is from Somerville, MA. and we went there a few times when I was young and thus my Boston affection began.
The most gut-wrenching moment may have been Red Sox ALCS 2003. I was on a cruise ship at the time and in a bar next to the casino. Every Boston fan was hooting and hollering as it looked like we were finally going back to the World Series. Then you could just see it slipping away until the extra inning home run stole it from us. Suddenly every New York fan was in your face. I had one lady scream at me directly "It's like winning a jackpot!". It sucked the life out of me. I truly felt we were cursed until the next season was finally savored.
It may be tied with the 2010 Boston Celtics Finals Game 7 - That got me the absolute most excited about any sporting event ever because we never seemed like a team any one gave a chance. Ever....and then we came into the playoffs and we just kept mowing down the best of the best. I would have never been disappointed if we lost because we played our hearts out. That is, until we got to game 6 of the Championship Series. Then it just got painful. Perk goes down and then game 7, we had it won until 6 minutes to go and then the refs and craziness took us out. That to me was the most painful Celtics loss. If we would have won it would have been the greatest win.
1986 Red Sox World Series Game 6 - I can remember thinking we finally were going to win the World Series. My dad had never seen it happen and he passed the previous year a fan all of his life and I remember thinking we finally was going to win it. And then the Buckner debacle in which I've ended up feeling more sorry for him then the Red Sox themselves over the years. He was really a good player and his name was forever tarnished. Sad.
1978 Red Sox 1 Game Playoff - I was 11 years old and ran home from school to catch this game on tv in my room. I was on pins and needles until Bucky Dent yoked my heart out. That was the 1st time I ever experienced Red Sox pain. Not the last though. I actually remember seeing the 75 Red Sox and I remember my dad aching over it. But I wasn't a Red Sox fan yet. I was actually cheering for the Reds. I was a fan of the Big Red Machine then. (I was 8 yrs old). That all changed when my dad took me to Boston. I've been loyal ever since.