Putting together a roster that competes for and wins Stanley Cups, apparently.
I don't really think the team always has "cap issues" though. If your team is on a 6 year stretch of making the playoffs every single year, making 2 Stanley Cup finals, and finishing near the top of the league every year, while managing these supposed "cap issues", then I'd say you're doing a pretty good job.
The problem that many GMs run into is that they try to run a team and be at or close to the cap every year while being competitive. It's usually one or two awful contracts that they hand out though that handcuffs a team so badly that their run of success is short lived. If you really look at the Bruins roster and the contract situations, there really isn't an AWFUL contract. There are certainly a few guys getting paid slightly more than they are worth, but not to the point where they aren't moveable if necessary or completely prevent the team from doing anything. Even with the Iginla bonus, this team still has the necessary cap space to make a move to improve the team come deadline time. The only contract I guess you could say is "awful" is the Kelly contract, and even then, it's only 3 million in the grand scheme of things. It doesn't handcuff them, persay.
While we don't necessarily agree with a lot of the moves he makes, and doesn't always get the guy we want, and sometimes trades away the guy we like, his mismanagement of the cap is horribly overblown on these parts. He does show loyalty to his guys. He overvalues some players that he shouldn't, and doesn't value some of the players he absolutely should.
I'd say his biggest mistake as GM was giving Seguin the extension too early. He almost managed to convince himself that he made a mistake with that deal, and along with the supposed off-ice issues, managed to convince himself and others that trading him was the right thing to do. That contract looks like an unbelievable steal at this point. But if anything, it got him (at the time) a guy who wouldn't produce as much offensively, but was still a gifted offensive talent for a million and a half less, and was able to slide in one or two entry-level contracts with one only getting a small raise on a new deal. Obviously, Eriksson hasn't lived up to his billing, and that's the thing. Those things happen. I know we all had problems with the Seguin deal because we knew what he'd become. But nobody on here, NOBODY knew that Eriksson was going to underperform the way he has. And sure, you can put the onus on Chiarelli for not being able to see that, but its not exactly common for a guy to suddenly produce at nearly half his normal pace out of nowhere. With no real discernable injury (other than the concussions, which we agree he's sorta past at this point), it was really difficult to predict that. I know you and others have pointed to the lockout season as a potential sign, but do you know how many guys have had down seasons before? You can observe a player as much as you want, as long as you want, in every scenario, but until you actually place him in your own system, with your own guys, with your coach, you truly don't know what you will get. And that's the risk with every trade. We have people clamoring left and right for Jordan Eberle, for example. But we truly don't know if he will ever fit here.
And again, your right to criticize why he makes the deal then, if he knew what he had in Seguin and had already seen what he did in this system. But even in trades, you don't deal in absolutes. That this guy absolutely will do this, and this guy absolutely won't do that. You have to take chances. Some will make you look like a genius (Horton, Seidenberg) and some make you look like a bumbling fool (Eriksson). At the end of the day, he managed to put together a successful product on the ice, and nearly has 2 Stanley Cups to his credit. The way you describe him, its as if the team managed to put itself together and succeed in spite of him.
And does that absolve him from any criticism? Absolutely not. If this team continues to trend in the wrong direction, and it gets worse? As in they get knocked out in the first round this year, and then again next year? Or even worse, miss the playoffs? Then the idea of going in another direction becomes a real possibility.