Getting Evander Kane, Blake Wheeler, or any of these other guys is a bit of a pipe dream, I think. Shero would have to pay a hefty price to pry that kind of young talent away from a rebuilding team. I mean, Wheeler would have been an excellent target a few years back when he was still with Boston. He was stuck on a very deep team and wasn't getting the consistent opportunities under Julien that he needed to thrive. Atlanta / Winnipeg bought low and are now reaping the benefits. Without knowing anything that went on behind the scenes it's tough to criticize Shero for not making a trade. For all we know Boston wasn't going to deal him to a fellow powerhouse no matter the price, especially considering the talent of our centers. That probably doesn't get any easier after the Neal trade. Still, those opportunities are out there from time to time and if we're ever going to get another one of these players outside of the draft it's going to have to come in the form of some shrewd trades. Emptying the farm system and dumping draft picks will net you some pretty good players, but you'll likely be paying market value on their upcoming contract and nobody will accuse you of getting great value.
Honestly though, people need to temper their expectations. Good proven top 6 forwards come at a high price, especially if they are on a cap friendly contract. Shero's goal should instead be to find quality players with decent skillsets who are flying below the radar. Stempniak is a prime example. He's played for awful teams for much of his career and as a result not many people know anything about him. His numbers are ok, not spectacular. Seems like a 2nd line tweener, perhaps best suited as a third liner. His peripheral numbers, however, are quite good. He's been a positive territorial player for the last few years on the dumpster fire that is the Calgary Flames. He takes a good number of shots, which is a valuable skill. If you want to use the eye test, it's evident that he's a good skater who can handle the puck well. He's crafty. He can score. He can play on the PK. He's basically the swiss army knife of hockey players, and he's precisely the kind of player that this team should be targeting more often. No, he's not Evander Kane, but he won't cost the arm and leg that Kane will and on top of that we can easily retain him without making sacrifices at other positions.
Getting good value on underrated players is extremely important when you have two guys with monstrous cap hits. Letang will soon make three. They can come in the form of younger players (Neal, Niskanen) or veterans (Kunitz, Jokinen, Stempniak, Goc). I could even include Ponikarovsky even though he didn't work out because we didn't lose anything worthwhile and he was worth taking a chance on. Not every move has to be a big splash, and no move no matter how calculated is guaranteed to work out the way you want it to.
While Shero's latest moves have been good, and he's made some great trades during his tenure here, he's also made some pretty boneheaded decisions over the past year or so which go against the philosophy I laid out above. He drastically overpaid for players who were essentially done in Morrow and Murray (and fans of their former teams were saying as much at the time). I won't mention the Iginla trade because again, you can't be completely results oriented. It was a fair price and seemed like a good match at the time. Clearly his season with Boston is showing that he's far from finished, and many would argue his failure here had to do with being misused and miscast.
Moving on, Shero made a big mistake in signing Scuderi to one of those retirement contracts. It's the kind of signing that at best works out okay and at worst is really, really bad. There's just not much upside to signing an aging positionally sound shot blocking defenseman in his late 30's unless he comes at some kind of bargain. Scuderi did not come at a bargain. It's an especially puzzling move given the depth we had at the position. It hasn't worked out well so far, and there's not any reason to think that it gets better from here. Moreover, the logic behind signing Scuderi bodes well for the return of another defenseman that makes us a worse team when he's on the ice - Brooks Orpik. Having mediocre players on bad contracts is just as impactful to a team's future prospects as signing good players to cap friendly deals, especially when the entire organization is still under the delusion that they are useful players who need quality ice time.
Re-signing Dupuis sort of falls into the same idea, except that he is actually still a fairly decent player. The problem is the term of the contract. He's a guy who brings one element in spades, and that's speed. Not the kind of player I'd be hitching my wagon to at the tail end of their career.
Everything comes full circle with Fleury. Despite being a train wreck in the playoffs year after year, Shero refuses to cut ties with him, even when the new CBA presents something of a 'get out of jail free' card. The next thing you know Bylsma is endorsing Fleury as the de-facto starter in a press conference and Vokoun, one of Shero's best acquisitions, gets thrown under the bus. It's all rather maddening, really.
There are times when Shero does seem to 'get it'. Others not so much. He's become as much of a jekyll and hyde GM as the goaltender he refuses to divorce. During the offseason I have no clue if he's going to rob Gillis blind in a deal for Kesler or if he'll re-sign Orpik to a contract worth $6m a year. Maybe he'll do both. As long as that's the case, this team will continue to be a tier below the true elite teams despite having as good of a core as anyone.