I know it's hard to say as a flyers fan but aren't you forgetting a cpl penguins teams, also? Im thinking they had a good run in the 90's and 10's maybe?
It's all good, though, I'm from the Pittsburgh area and had to deal w/ them raising the Cup against the RedWings a few times in small local bars. The last one, when the Winds couldn't jam it in in the final seconds, I ran n hid in the bar's kitchen while the owner n just about everyone else celebrated n tried to get in to buddy my ball's, for about 10 minutes. Was not too fun of a night.
As for why, the RedWings, Kert, it all started w/the Russian 5, Sergei Fedorov, and him being the hot rookie card when me n my Ol'Man(gone but never forgotten) started collecting hockey cards.