It may be like me and fandom of Michael Jordan......
I was young and just getting into basketball in 1993 when Jordan was already a two time champ. As the champ, I was rooting for someone to beat the Bulls. After all, who doesn't like a good underdog story?
Well, he beat the Suns, then the Sonics, oh and the Jazz twice. I was disappointed each time, but at the end of the period I couldn't help but look at the bigger picture and say "wow, that guy sure was damn good." Now after the fact I celebrate his success instead of being disappointed by it. In fact, I've learned to appreciate him more in retirement in which I've since purchased my fair share of Jordan dvds.
The same sort of goes for the Blackhawks. They beat the Bruins so I should be pissed at them, but I can't help but respect their three cup run in recent history.
You can root against someone but at some point with continued success you can't help but tip your cap.