The thing is, where most fans and even a lot of GM's look at what will benefit the team this season, Ken Holland is looking at this season, as well as 5+ years from now.
Ken Holland traded a first-round pick for Kyle Quincey.
Ken Holland threw crazy money at Zach Parise and Ryan Suter. Had we signed them, "5+ years from now" wouldn't have been a thing anymore. We would've spent the duration of those enormous contracts living year-to-year, selling off young, homegrown assets when they became too expensive to hold on to. (Not necessarily saying it wouldn't have been worth it. Just saying.)
Ken Holland traded one of our better prospects and a second-round pick for a rental so that we could limp into the playoffs and keep The Streak alive.
Ken Holland courted Stephane Robidas, who was injured at the time and, as he's failed to establish himself as a regular on the Maple Leafs' blue line, is pretty clearly washed up.
Ken Holland has pursued Rick Nash, Alex Edler, Jarome Iginla, and probably every other big name under the sun. Eventually, we're going to land one of those big names. Because, at some point, you have to. We added Rafalski in the summer of '07 and Stuart in February of '08. The Kings added Williams and Richards and Carter, and then Gaborik. The Blackhawks added Sharp and Oduya and Hossa.
That's half the reason why you stockpile assets in the first place - so that you can trade them. You don't wait to see how each and every one of your promising prospects pans out. If you have your seven D slots filled, and you've got as many as five really good D prospects in the pipeline, and you're a Keith Yandle away from being a Cup favorite, and Keith Yandle is - for the first time ever - known to be available, and you have three more years left with Datsyuk...do you really say, "Well, we have to think about 5+ years from now"? I mean, sure, of course the future's a consideration. But, um, I'm personally not willing to wait 3-to-5 years to see if one of our prospects (at least two of whom inevitably won't be Red Wings, if only because we're not going to have enough room) becomes as good and valuable as Yandle is right now. Our blue line doesn't move the puck well enough and doesn't produce enough offense. Smith isn't producing. Ouellet doesn't have Yandle's offensive upside. Marchenko is a shutdown defenseman. Sproul is a couple years away from being a regular, never mind an impact player. You're telling me we can't afford to part with any of these players, even if we're getting a top-pairing defenseman who can score 50 points for the scoring-challenged Coyotes?
We need a Rafalski, and we need him while Datsyuk and Zetterberg are still dominant players. We're going to have to give to get him. If we're going to wait to see if one of our prospects becomes a Rafalski, we're taking a bigger risk than the one we'd be taking if we acquired that player. Because, we don't know where we're going to be 5+ years from now (though, we do know Datsyuk will be gone and Zetterberg will be a shell of the player we have today and Nyquist and Tatar and DeKeyser will be making serious money). I'm not saying we should trade one of our untouchables. I'm assuming we can add a Yandle without having to part with one of our crown jewels. Which is one of the perks of having a ton of assets. You can afford to part with a couple pieces. Pulkkinen isn't a key roster player for us right now, nor is Jurco, nor is Smith, nor is Ouellet, nor is Marchenko, nor is Sproul, nor is the pimple-faced 18-year-old we'd draft with our mid-to-late first-round pick. Remove two or three of these pieces and we're still a contender, and our future is still extremely bright, especially with a top-end defenseman in the prime of his career being added to the fold.
We're contenders. Datsyuk and Zetterberg and Kronwall and Nyquist and Tatar and Sheahan and DeKeyser have all avoided major injury this season. The Eastern Conference crown has never been so up-for-grabs. We should make a push. Why say, "Well, it's great that we're contenders, but what about 5+ years from now?" Well...maybe we're contenders 5+ years from now. But...we're contenders...right now...? I'm not talking about selling the farm. I'm talking about moving a D prospect plus Pulkkinen/Jurco. If that's completely out of the question, then we're never going to make a meaningful trade and this team is never going to reach its full potential. We draft and develop well, but not well enough that we can say, "Y'know what, let's try to win with an entirely homegrown roster." Why would we make that a thing? Even if it's possible, it's certainly not realistic. Every Cup-winning team that has ever been has needed some outside help.