He picked Subban, Pacioretty and McDonagh, but they are exiting their primes as we speak. These guys were picked 15 years ago!! Galchenyuk, KK and Sergachev all top 10 picks very mild return on the investment so far. Other then that our only 1st round picks sitll in the show are Beaulieu and Tinordi unless I'm mistaken... not exactly world beaters. All in all a very underwhelming return for the amount of quality picks.
Subban, Pacioretty, and Mcdonagh were all actually picked on the same year which is a massive home run.
His run from 03-07 was generally strong. After that, the well dried up up too much. It was a combination of poor drafting, the team having later picks in the draft, sprinkled in with trading picks (Tanguay for a 1st), and trading prospects who made it (Sergechev for Drouin ughh).
I think they have restocked the cupboard though in the last 2-3 years, so we will see how that goes, but outside of 07, when they drafted arguably 3 elite players, I think the problem has been finding elite guys, instead of just good players. I think while the habs have an interesting crop of youngsters right now, that elite player is still missing.