Raise your hand if you actually think that a roster player or prospect will be traded this off-season. Or that Holland will be fired. Or that Howard will not start the majority of games next year. Or that the government had anything to do with 9/11.
If you said yes to any one of those, you are a crazy person.
This is an impossible subject to speak definitively about because many of the positive and negative outcomes of a GM's decision are dependent on a range of factors largely beyond their control, so a case by case basis either way is either cherry picking or at best indicative of minor trends. The only real test is overall results and overall comparisons to others.
First off, it has to be acknowledged that he inherited a great situation. Stacked roster, no salary cap, devoted fan-base, supportive owner and a ninja European scout. Could do a lot worse.
Equally, it has to be recognised that the job he did in extending that situation and improving the infrastructure around him surpassed all expectations. Anyone remember the wings being 'too old' and in terminal decline even before the salary cap was introduced? The wings dropping out of the playoffs within two years has been an annual prediction since the lockout over a decade ago. Hasn't happened.
Of course much of that has been dependent on coaching and drafting, neither of which he can take much direct credit for, particularly given our best draft picks have been late round specials. But crucially, the primary aspect of management is to find good people you trust and empower them with the trust and conditions to do their job well. This is perhaps, along with his patience, his biggest strength as a GM.
One also has to agree that although the post Lidstrom era has been less fun than hoped due to Suter's 50/50 choice being dictated by his ill advised decision to join his mate in the mountains, the Red Wings have done a remarkable job at circumnavigating the primary objectives of the combination of draft and salary cap, that being parity and a rotation of who makes the playoffs. Of course, a quicker route to the big prizes is to fail badly in good draft years, but the roster has remained too strong for this to be appropriate.
The over-riping development model, for the most part has been crucial to sustaining this. Because the team has remained at least partially competitive, it has been important to only rely on prospects when they are ready. If the team was in worse shape, they'd be up sooner.
And yes, the late round gems have kept on coming , from D & Z to the comparative huge successes (ie statistically massively overachieving compared for the norm for their draft location) of Hudker, Flip, Ericsson (and even Meech to a degree!) in '02, Quincey in '03 (though waiving him was such a poor choice at the time, he has eventually proved his worth), Franzen in '04, Abdelkader to a degree but certainly Helm in '05, (06 had real talent, but none made it here for different reasons), Andersson in '07 (just about..), Nyquist in '08, Tatar in '09 (and Jensen and Ferraro and Callahan may yet get there), Mrazel, Pulks in '10. Subsequent years have a very good chance to be equally successful or better, but its too early to say.
Howard (goalies are different!), kopecky, Smith & Sheahan are about par or just below at this point, and only really Kindl, Mccollum and maybe Emmerton are real disappointments.
Trading & FA is a bit more sketchy, but its important to balance recent years with earlier ones. Every Legwand (which if you prioritise the streak is a wash), Weiss, Tootoo, Modano, and the later Sammy/Cleary versions or even Robert Lang or Cujo if you want to be harsh is more than countered by Cleary/Sammy first time, Rafalski, Chelios, Larianov (second time I think was KH), Hull, Hasek (both!), Lucky Luc, Brad Stuart, Alfie, even drew Miller!
Also worth noting that barring the Robert Lang deal where Washington ended up with Mike Green, the wings have won on every single trade for draft picks or exchanging picks in the last 16 years. The only other exception was a pick that was eventually used for Patrick Sharp, but that changed hands about 4 times before the draft in which it was used!
The more recent trend is not that encouraging, but how many of the poor trades or FA signings have hamstrung us? Weiss is the only albatross, unless you decide that Howard's contract is as well, which is hardly a forgone conclusion given pre-injury performance levels. Of course the Franzen/Hossa thing will always be a frustration, but even despite people bagging him, until their is a cap reclaimation (NHL changing the rules AFTER the event), the Franzen contract has actually been mostly very good value.
Of course, what happens next is more important than what happened previously, and in the last 2 seasons the jury is out due to the unfortunate results of trades and Free Agency (such a shame about Cole, who looked a really nice fit in the top 9). So this summer is not insignificant. If Holland can bring in any quality FAs and get Kindl and Weiss of the cap, that would be success I think. but we can wait and see I guess.....
One thought I will leave with...imagine how much stronger his legacy would be if we hadn't seen the loss of Vladdy's norris levels of play, Fisher's punishing hitting or Grigorenko being seen as almost Kovalchuk good before his crash. We could easily be a cup or two better off.
If I did as bad a job as Ken Holland over the last few years at my workplace I'd have been fired about seven times by now.
Remember, Kenny gets paid a hell of a lot of money to supposedly make this team better. What has he done to make it better since Lidstrom retired? What part of his actual job has he done besides sit on his hands and take the easy options time and time again? This team has SCRAPED into the playoffs for two seasons running and his response is to re-sign two of the worst players and give himself a pat on the back?
I've said it so many times over the years and I'll keep saying it in stronger terms with every ridiculous move he makes. Ken Holland is a fraud. Without Håkan Andersson he would have been found out years ago. This roster is his product, the Franzen contract will be his legacy, and it'll be a miracle if we keep the playoff streak alive with a weaker and somehow OLDER roster than before.
Bottom line: Holland has failed year after year to replace Lidstrom and Holmstrom. His signings in the last few years have been nothing short of laughable. There is loyalty to players but more importantly is loyalty to the fans to do his job and create the best roster in his power to compete for the Stanley Cup.
Unless there is another Lockout around the corner this should handcuff the Hawks pretty badly. If I got my math right thats over 25% (close to a third) of their current capspace tied into these two players.
Cap is gonna keep going up. These contracts won't be bad in 3 years time