SOW this isn't a shot at you, but there does seem to be a feeling that trading a young prospect only means we are going to get a 34 year old guy with 1 or 2 years left to play. Look at the 3 big F that got moved so far this off season: Kesler, Neal, and Spezza. None of those deals broke the banks of the teams that picked them up. Trueth be told, we could have made all 3 of those deals, been a much better team, and still had some young guys left over. Not to mention we had the cap space for it. While prospects are nice and all, most never pan out. That is true and will always be true. Same was true with the Nash deal, not getting O'reilly, and Ryan. That is 6 big time F that have been moved or available lately that we could have had, failed to get, all but 1 are under 30. Meanwhile we have been 15th or so in scoring the last 2 years, with most of our prospects burried in the minors.
Spezza wasn't a need, Kessler wanted either Anaheim or Chicago, and the Pens shipped Neal out west.
You said he "never" did anything to build for an immediate run and sacrifice the future. He did. Yes, it was a while ago, before the Cap. But that's not "never".
*edit-- 4 of 9 first rounders traded since 2006.
So Holland trading down first rounders because the player he wants is still available is hurting the teams future? I'd hardly call trading a late 1st for 2 second rounders sacrificing the future. Also, precap era trading firsts wasn't a big deal. They brought in players they wanted and had the money to keep them. Not to mention they were able to outspend almost any other team in free agency. Late first round picks were fairly meaningless for this franchise back then. You also can't consider trading a late first rounder for 2 picks hurting the franchise either.
The ONLY first round pick traded you can make any possible case for is the Quincey trade. That is one pick. One pick will not hurt this team in the long run.
Has he made moves for an immediate run? Yes. Has he ever hurt the future of the franchise by doing so? No.