Discredit the Penguins because of winning the Crosby lottery like it takes one superstar to win a Stanley Cup. It’s so easy that every team has done it.
I think the difference between Pittsburgh is that Pittsburgh lucked out with the lockout for Crosby (they probably wouldn't have been 1OA if a season happened AND tanked for 1OA 2 years with Fleury, Malkin. Then add Staal at 2OA and that puts a salty taste in people's mouths. The team made other moves that put them all the way to the Cup though, so kudos to their management for that (home run on Letang, trades for scoring wingers like Kessel, Hornqvist, Neal). But those last three aren't really rebuild moves, they're the opposite if anything.
In the same fashion, if Edmonton won the cup th elast 2-3 years, it wouldn't have been considered an amazing rebuild by their FO. They weren't smartly picking first overall. They were just bad.
Chicago's rebuild meanwhile, did consist of some really good picks. Kane aside and lucking out on Toews, Keith, Seabrooke, Panarin, Saad, Shaw, Hjarlmarlsson were all either homerun late picks or hidden gems, and the Patrick Sharp trade was an big win also.
I'd say the Chicago rebuild is more impressive and their management had more of a role in actively turning it around, while Edmonton and Pittsburgh were more passive. Comparable to Chicago today, I'd say is NYR's rebuild. Great bunch of trades, selling high on Brassard, Zuccarello, McDonagh) with a couple nice picks and one lottery, and acquiring some big names like Panarin in UFA, trading for Trouba and Zibby.