I'm not sure which is worse, being in contention and then losing, or being completely terrible. There was very little redeeming about 2000 for Boston sports (although things did get better the next year, of course.)
Being in contention and then losing, easy.We Boston/NE sports fans have been spoiled this decade. Keep in mind that in 2000, Red Sox fans never thought the Red Sox would ever win a World Series again, everyone knew the Pats were awful, and the Celtics would never regain the glory days of the 80s.
It would have been hard to predict in 2000 that over the next 8 years the Red Sox would win 2 World Series (the first in dramatic fashion, after coming back from being down 0-3 to the hated Yankees), the Patriots would win 3 of 4 Superbowls, and the Celtics would beat the heavily favored Lakers to win banner #17 (again, in dramatic fashion, by blowing out the Lakers in a record final game).
Now a decade has passed, and we expect the same. We have been spoiled. So when we don't get it, it is crushing. Before, we expected to lose, so losses weren't so bad. I gotta go with 2009 being worse than 2000.