I see people making this argument a lot but I don’t think it has as much relevance as people think it does.
Most of the disparity between the current state of the Caps and Pens (and their prospect pools) can be explained by their drafts, trades, and FA acquisitions from the 2018 draft onwards. That is, moves that took place AFTER both teams won their Cups.
There is a pretty stark contrast when you put their last 7 drafts side by side:
IMO Washington’s pro scouting has also done a pretty good job in recent years. Signing longer term pieces like Dylan Strome to good value and also picking up guys for shorter term who can later be flipped for picks at the TDL if need be.
There’s no question that Pittsburgh as a whole has been the more successful franchise. But IMO people are excusing their current paucity of prospects and young talent as a necessary byproduct of that success, when really a lot of it has to do with mismanagement by Hextall et al in their more recent, post-contention period.