Since we were really feeling the cap when we were still paying Zetterberg around $2.5 million/season?
But all in all, the "you could do better" thing hangs over the last four years like a cloudy sky on the verge of rain.
That is a ridiculous standard, and if you were to apply it to any other GM in the history of any sport you're not going to find even one you think is adequate.
In the span of a few seasons we lost Yzerman, Shanahan, Hull, Robitaille, Fischer, Larionov, Hasek, among others, plus maybe the best coach of all time. Chelios went from a Norris candidate to depth player, Draper and Maltby from invaluable role-players to guys filling out the roster. We'd lost in the first round, second round, and first round. We had a lot of good prospects and could afford to lose some. Plus we made the transition to the cap era.
Holland made some moves, some were decent, some not so much. We signed some cast-offs that no one else wanted, brought up some young guys, signed one big UFA. It worked and we won a Cup. It wasn't luck that we had a bunch of cheap guys. It's what you have to do in the cap era. Then we had to start paying guys and trying to fill the rest of the roster with bargains. Some of those guys were decent, some not so much.
It's just not reasonable to expect that we should have had a replacement for Lidstrom before he left. The only way to get that is to get lucky, either with a prospect or someone else's cast off. If you want someone already proven, you would have had to give up a lot to get them, and we couldn't have fit them under the cap. We would have had to make the team worse in previous years. Maybe in hindsight you can say they should have, because we haven't done much in the playoffs anyway, but really you all would have just been bitching about mismanagement back then.
Some people are completely backward in thinking that the biggest needs, the biggest losses, should be the easiest to fill. Fact is, those holes have the fewest available options and the least margin for error. That's why almost no one, in any sport, in any era in history, has much success filling them without a hitch.
Nothing Holland could have done would have been better than landing Suter and Parise (particularly since we wouldn't have had to give up anything), and he put us in position to make a strong play for both of them. Unfortunately, it didn't work out. But we're still in a good position to add more, and we still have a well stocked prospect pool. Maybe, probably even, things will get worse before they get better. That's the nature of the beast. We need stars and those almost always come through the draft. Once we have our next generation of stars, then will come the time to start making trades and looking for a good UFA or two to put us over the top. Hopefully at that time, some of the young prospects we have now will emerge to fill some roles at bargain prices.
Sure, we could make a move or two now and it might work out. Or not. Look at the Rangers, Philly, San Jose... Maybe Holland could have done better. But who actually has?
Pittsburgh? Cup winner, last three years lost in the 2nd, 1st, and 1st round. Found some nice fits at forwards, including one absolute steal of a trade, wrecked their defense. Looking good this year, maybe they'll go somewhere, maybe not. Their best players can't stay healthy, probably going to have cap troubles again in a couple years.
Chicago? Cup winner, sat watching the TV hoping for Dallas to lose to put them in the playoffs the following year. Two first round losses. Looking good this year... Likely cap trouble again next year.
Boston? Cup winner, lost in the first round last year. Looking good... maybe some cap trouble next year.
LA? Cup winner, had to fight down to the wire to make the playoffs, likely the same this year. About $15M to fill almost half their roster next year...
Anaheim? Doing great this year after plenty of struggles since their Cup win. Big commitments to their stars likely to create some cap issues down the road...
Pretty much all that separates us from any of them is they have young stars while ours are aging. Most of them were irrelevent not long ago, and will likely end up back there before too long. Come back when their stars are aging and see how much better they do than Holland. I bet none of them do half so well.
What Holland has already done proves that he's a great GM. He's had some luck, and a great staff to work with, but he's still been great. No matter how successfully we make it through our current transition or the next.