In Trevor Timmins' time with the CH, he has drafted the following on the top 50:
A.Kostitsyn, Urquhart (bust), Chipchura, Price (elite), Latendresse, Fischer (bust), Maxwell (bust), McDonagh (elite), Pacioretty (elite), Subban (elite), Leblanc (bust), Tinordi (bust), Beaulieu (bust), Collberg (bust), McCarron (bust), DeLaRose, Fucale (bust), Scherbak (bust), Juulsen, Sergachev (potential to be elite)
=> That's a 50% success rate and 4 or 5 elite picks
To me, it is the number of picks traded away that Timmins didn't have to hedge his late 1st round gambles:
No 2nd in 2004, No 1st in 2008, No 2nd in 2009, No 2nd in 2010, No 2nd in 2011, No 2nd in 2012, No 2nd in 2014, No 2nd in 2015, No 2nd in 2016
That is nine top 50 picks, or half a dozen core players that he did not get a chance to draft.
I do not think the problem is Drafting or Timmins at all.