Good old strawman, always the best argument...
Some people can't seem to understand that you need the resources to make a trade (cap-space, assets) and also a player to target who you can fit in and who the the other team wants to trade for what you can offer. Then you have to take into consideration that other teams can make offers as well, that they might have more resources available than you do, and / or have assets who are a much better fit for what the other team is looking for. On top of that, some players will have clauses which give them some level of control as well, and some teams may not be interested in giving you certain players either. A GM cannot force other teams to trade with him.
The cap has roughly stayed the same since Holland took over, and the team didn't have any cap-space to begin with, while being harmstrung by some contracts you had a hard time moving. Yet Holland vastly improved the quality and depth on offense, brought in quite a bit of help on defense (Keith, Ekholm, Kulak) and tried to find a solution in net (going after Markström, signing what was one of the top options available at that time in Campbell). He tried to bring in veteran experience with Keith (and the NHL robbed the Oilers of the cap-benefit they should have gotten), he brought in Kane below what would have been the regular cost of such a player due to the circumstances. Same thing with Perry. He got Hyman at a very affordable rate. He got creative in trying to squeeze in a nominally more capable player than the remaining league-minimum salary would allow for when signing Brown. That backfired, but you can hardly claim that he didn't try to go with high risk / high reward on that one. Now he brought in Henrique and Carrick, hardly nothing either.
You can certainly state that quite a few of his moves didn't work out, and in some cases that he should have known better from the get go, but that is true for virtually every GM. But one thing one definately cannot claim about Holland, is that he didn't try to improve the roster with what was available to him. What Holland couldn't do, was magically create cap-space out of thin air thanks to timely LTIR-cases.
His performance as GM has been fine. Not great, but far from bad. The team is much better than it was when he took over, all while having no additional cap-space.
Needless to say, only one team can win the Cup every year, and a lot has to come together to be the one who does it. You need to peak at the right time, not run into a team that has your number, you have to stay healthy, and luck plays a role as well. There have been plenty of cases where a GM did a very good job, the team worked as well as it possibly could, yet it still wasn't enough due to circumstances completely out of the hands of the GM, coaches or players.
