They became powerhouses because they got talent from being shit, but then also made good moves after that. They didn't just get lucky.
All this discourse made me think how the 10 cup final team came together. Most of the best forwards were drafted (Richards, Carter, Giroux, Gagne, JvR) and the others were acquired via FA or trade (Briere for FA, Hartnel technically and Leino were traded for). All of the role players were signed or traded for (Laperrier famously signed and announced to be the 3C but dude was RW).
All of the D was traded for I believe, but they traded for good D. Timonen and Pronger both #1 D. Carle and Coburn both great complimentary partners (Coburn could he fine on his own but Carle really thrived with Pronger). The bottom pair was a mess and not really notable.
The goalies were signed except Leighton who was picked up on waivers. Don't need to discuss that anymore.
Holmgren was great at acquiring talent and then seemed to rest on his laurels after the cup run cause the Flyers stopped trying to acquire top talent. Lots of over the hill signings on D, coupled with the loss of Pronger. Then culture reared it's ugly head when Carter and Richards were traded. The returns were great and could of set up another run, but the D and goalie situation could never be figured out. Then the prospect pool was barren from the years of acquiring top talent, and then mediocre talent (1st for Eminger, 2nd for Meszaros, 2nd and 4th for Kubina). And then some misses with drafting and undrafted FA (Marshall and Klotz in 07, Goulbourne in 13, Brandon Manning undrafted FA). Hextall did great to clean up the cap and load up on picks, but also acquired horrid players. He also had notable picks miss.
So TL'DR the Flyers built a cup team by acquiring top talent, and then began to mire in mediocrity when they stopped acquiring top talent (hello Risto). And now they are stuck in a culture war where they will continue to eschew skilled players for mediocre try hards. Thus continuing their mediocrity.