There are some great stories in here. Mine is a little bit different because of when I started watching SU hoops.
I was really a bit too young (9 years old) to fully appreciate the devastation that was Indiana. So for me that doesn't really register (thankfully). The Richmond game I was just starting to become an SU basketball fan, but didn't watch the game, and was too interested in Loyola Marymount, LaSalle, UNLV and Georgia Tech that year. So that loss didn't sting.
I finally came to my senses in 1994, and really started following SU full time. The Missouri loss in the tournament hurt a lot because I had a love affair with Adrian Autry that year. That one really hurt. The Arkansas game was a dagger, but I didn't expect the team to go too far that year, so it wasn't as damaging. The way they lost was awful, but it wasn't as bad (for me) as the Missouri game.
Really the UK loss in 1996 was the worst for me. I was 18, had attended half a dozen games at the dome that year, loved John Wallace and Laz Sims, and couldn't believe it when they made that run. It really FELT like destiny to me. This team was destined to slay Goliath, like NC state had done in 1983.
When Wallace fouled out a part of me died. I was never as "true blue" an Orange fan after that. That lose popped my innocent/naive cherry as it were. I sat in my living room with my girlfriend beside me staring at a blank screen after the game ended. And...just kept sitting there. I must have sat staring at that blank screen for 30 minutes. I didn't go to school the next day, and was gutted for weeks over that loss.
It's weird, because in hindsight, they shouldn't have won that game. As a Syracuse fan today, I wouldn't expect us to win. The though, I thought this was a fated journey and that the good guys would always come out on top. That's when I realized sports, and life didn't always have a happy ending. Melodramatic? Sure. But it's the way I felt.
Another funny side story -- I was at the Landmark Theatre waiting for the Jerry Seinfeld concert to start in 2005. I had the UVM game recorded, when all of a sudden, everyone's phone in the bar area started blowing up. There was this collective groan out of everyone there, and the murmurs began that SU lost in overtime. I was pissed off, and beside myself. I couldn't believe it. I walked into Seinfeld, laughed my ass off, forgot about the game, and never watched it. I don't know what or how it happened, because I've never seen it. So thank God for Jerry Seinfled, because I missed a game I'm sure would have been an all-timer for me. So here's my list of three.
1) UK
2) Mizzou
3) Arkansas