I'm from Boston. Take your pick.
Still have to go with '86 Game 6 World Series as my #1. 2008 Patsies Super Bowl was pretty devestating as well. So was the 2012 Super Bowl. Aaron Boone, 2003. Bucky Dent, 1978. Celts snatching defeat from the jaws of victory from the Lakers in Game 7 a couple years ago. Brutal.
Let's put it this way...as bad as the Bruins loss was, it might not even register in my Top 10.
Agree with all of the above 100 percent
Esoteric verbosity culminates in commutative ennui.
De gustibus non est disputandum