Dougie is hands down amongst the greatest GMs in Hockey. McPhee in Vegas is definitely raising some eyebrows (man, did he finds some immense hidden talent and with the karlsson extension under 6M per, he is impressive), but Dougie has put together teams that have competed for the cup every year for 15 years, missing the PO's once. The highest pick he's had since 2004 is #9, once. Other than that, 12th in 2005 (traded up to 8 for seto) or 13th in 2007 (traded up to #9 for cooch). He has had the lowest draft position of anyone and the greatest playoff making record of anyone, most wins(or nearly), most PO series wins (I think) since he took the helm.
We forget how much chicago sucked before they were good. We forget that Pitt was terribad for a while and got 100% lucky in the 2005 lottery for crosby which transformed them. LA has had a bunch of terrible years. Edmonton has picked first a bunch and still sucks. Dougie has taken a traditionally unattractive place to play in some out of the way non-hockey spot like SJ (compared to Tor, MTL, NYC, DET, etc) and made it a destination for the leagues top players. He has traded shrewdly forever, signed very few bad deals (and no major bad deals), drafted well late, found off the radar free agent europeans, and just year after year, crafted rosters that have legit chances to win. Under any other GM, the sharks would need an extended rebuild to move past the jumbo-patty-boyle era. But with Wilson, that transition was pretty damn smooth. Now it looks like pavs may move on, and they still have a possible cup roster without him.
Yes, they have never won a cup, but they came within two games, and did so without the advantage of any top picks (unlike pitt that had multiple top 5 picks to create a team with crosby, malkin, fleury, etc)
All you can ask is to ice a competitive team every year that is fun to watch and then hope that they finally win one. They have two norris winners on the blueline forever. They have a super 1-2 at center with cooch-hertl and two 30 goal scoring wingers to boot. They have a deep pipeline of possible NHL forwards coming up this year.
Judging a GM exclusively by a cup is wrong. If the sharks are dead last in the league for 5 straight years, their chance of a cup go way up with 5 top 3 picks, particularly true in a cap era where elite talent on ELC's is extremely helpful. I judge a GM by making shrewd moves, finding gems that other teams don't, and competing every year for a cup. In those areas (trades, draft, Euro FA's, competing annually), dougie is unmatched.