Just even looking at the Stanley Cup winning franchises.
Blackhawks before their 3 cups:
Kyle Beach (11OA). We know how that began and ended
Jack Skille (7 OA). Bust, traded for Hugh Jessiman!
Bonus! Cam Barker (3OA) although they traded him for Nick Leddy (who won a SC).
Bruins before their 2011 SC:
Zach Hamill (8OA), traded for Chris Bourque AKA nothing.
Bonus! Best team in the league now. Can we mention the three successive picks in the 2015 draft?
Jakub Zboril, Jake Debrusk, and Zach Senyshyn (13-15OA) with Matt Barzal and Kyle Connor chosen with the next two picks.
Kings before their 2 cups:
Derek Forbert (15OA), traded for 4th rd pick
Thomas Hickey (4OA), waived, got nothing for him.
Jonathan Berniers (11OA)
Lauri Tukonen (11OA)
Pens before their 2 cups:
Derrick Pouloit (8OA), traded for 4th rd pick
Caps before their Cup:
For the lulz. Made a good draft pick in Filip Forsberg at (11OA) and then traded him for Martin Erat so essentially gave him away. doh.
Lightning before their 2 Cups:
Brett Conolly (6OA), traded for two 2nd rounders that became nothing
Callan Foote (14OA), 3rd pairing D just hanging on.
Slater Koekkoek (10OA) traded for 7th rounder and Jan Rutta
Fact is, picks in that range fail all the time and sometimes bring back nothing to really help even the best run organization (not saying that includes NYR). For the Rangers, we'll see with 2nd round pick Cuylle with Andersson.
Big thing with almost all those teams above is they got multi top five picks that played big roles and/or hit on a couple later picks like the Rangers have with Chytil and Miller. As I've said before, again and again. It comes back to Laf and Kakko. Those guys need to have the effect of "1st line" players or this franchise isn't winning much of anything.