Although I'm not the biggest Gillis fan, I will give him some credit in some of his acqusitions. He did a great job in finding Stanton, Magic Mike and Richardson from the reject pile of other teams recently. He signed some pretty good undrafted players in Chris Tanev, Eddie Lack and Kellan Lain is looking promising. His drafting is OK (good and bad). He has nothing much to show for it right now, his first pick CoHo was starting to look good, but he flipped CoHo for Kassassian, which is looking promising right now. Gaunce and Corrado are looking good, big question marks to Schroeder and Jensens. The most recent draft maybe his most promising with BoHo, Shinkaruk, Cole Cassels and Jordan Subban. It should be of note that the team has done pretty well during MG's tenure and finished higher up in the standings, thus it is harder to draft a good player.
He did make some really bad trades, which really hurt the team (ie - Booth & Baltard). 2 guys who ate up like $8M in cap space, but they didn't do much when they played and the coach generally went with other guys who made a fraction of those 2 in the big games that mattered most. If MG just stayed away from acquiring players with a high price tag (especially with Florida) and just went around acquiring relative unknown players who are still trying to prove themselves, he'd be doing pretty good.
Aside from his trades of the bigger variety, there are 3 things that stick out that I don't like right now.
1) I would say MG failed in finding big, strong grittier guys who are skilled enuff to battle though tuff grueling 7 game playoff wars. He's good at finding some good 2-way players like Tanev, Corrado, Standon, Richardson, Malhotra, Samuellson, Rome, Magic Mike, etc, but most of them are of the softer variety. While the Cali teams got skilled and bigger, Gillis's team got some skill, but generally lacked the grit. He did try to get some bigger, grittier, asshole types in SoB, Hornychuk, Sestito, Weiser, but none of them are exactly impact players. The best player in that department is probbly Kassassian. He's looking like the best of the bunch and is getting better, but he is only 1 guy and even he hasn't earned the full trust of the coaches just yet.
2) Gillis may have tried to live off the treasures of his predecessor a little too long. Signing Burr, the Sedins, and Lou to those long term deals may hamper the team for the next few years as all of them are showing signs of declining. Handing out no trade clauses left and right may also make things worst, as he may get stuck with an underperforming player eating up a lot of cap space and he is unable to move them.
3) Gillis squeezed out some great years out of the core he inherited (ie- Lou, Kes, Sedins, Schneids, etc), but he hasn't really found some star players to add to and help the core. Ehrhoff may have been his best, but failed to keep him. Hammer is good, but I won't say he's a star player. Sundin came for half a season, but he didn't have much left in the tank. Kassassian and BoHo may become core star players for the team, but both still have a lot of work to do and a lot to prove. The sad thing is that by the time Kass and BoHo become impact players, some of the current core may become shadows of their former selves and just not good enuff anymore, then we're constantly stuck in the cycle of not having enuff horses in their primes to win 16 games in the playoffs for a Stanley Cup.
Overall, I would give Gillis C+, maybe B-. I just hope someone will take Lou off our hands and hopefully the Sedins will start producing more. I don't expect them to win scoring titles again, but hopefully they can hover around point/game guys. I wonder about Kes too, he's up in 2 years and with the way things are going, I wonder if he looks for greener pastures and tries to win elsewhere. If MG cannot get him signed in the next year or so, it might be best to move him for youth (1 or 2 good young prospects). As of now, Kes is probably our best asset in the trade market to get something back of significant value.