It worked for LA, Chicago, Pitts, Washington, Colorado, and Tampa.
And failed miserably for Columbus, Florida, Edmonton, Atlanta, Phoenix, New York (Islanders), and you can include Ottawa in that group. Tampa, LA, Chicago, Pittsburgh all experienced significant front office or ownership changes which is the main reason why they became successful again.
Colorado also experienced some significant changes outside of the players they've selected through the draft, but it's way too early to tell whether they've turned things around. Washington just got lucky with Ovechkin, considering they didn't even finish last in the league that year.
Penguins are an exception here. nothing about asset management. The drafting of Crosby and Malking single hadedly made that team a contender. As well as drafting Jordan staal (who they took before toews. imagine Crosby malking toews) This team lucked out hard. The rest of their team are just all role players. Call that good managing, I see it as just luck. Hawks drafted toews and kane. But they also built a 4 amazing lines. and an unbelievably d-corps
Pittsburgh turned things around quickly because of Malkin and Crosby for sure, however they would have turned things around regardless...it just would have taken a lot longer (like the LA Kings or the St-Louis Blues). The reason they sucked to begin with wasn't because they made bad picks or developed players poorly. They had numerous high quality players they were forced to sell off because of financial troubles. If those financial issues never existed, then they would never have been a lottery team in a position to draft Ovechkin, Malkin, Crosby, Toews etc.
Their turnaround coincided with the introduction of the salary cap which made the salary discrepancy between them and the top teams ~$15m as opposed to ~$35m+, stabilization within the ownership group, and a new arena deal which would allow them to generate more revenue. They haven't drafted exceptionally well, but they've managed to repeatedly flip bad draft choices or expendable players for quality players and fill holes in their lineup with good free agent signings. Even when Crosby was out for a prolonged period of time, or when both Malkin and Crosby were out due to injuries, they still managed to be one of the better teams in the league despite having only "role players".