Quoting: tonyhzs
The window can extend with proper moves. Is EK for 4 years better than 7 years of Nurse? I think worst case is a wash for Edmonton. Edmonton doesn't really get punished for a few more years of Nurse cap retention based on cap economics going up, even marginally. Bad contracts drop off. What will motivate McDavid to stay is if any youth starts pushing more. If the current pipeline is really dry, and winning is on Mcdavids mind, he will leave regardless. There is nothing Holland can do to keep his guy at that point, so why not go for it now...
Problem is that when the cap goes up, it just means good players make more. You're investing a lot of money in Ekholm and Karlsson. When their contracts end, you're going to be looking at replacing them with more expensive defensemen, but with $4M less flexibility. What you're getting for $11-12M now, is going to cost you at least $15-16M then, just counting for the retention and not inflation of player salaries.
I agree with going for it now, at all costs. I'm only suggesting this particular cost may shorten the window of opportunity considerably.
Once you retain, that's locked in. You can't recover that cap hit or trade it off, so you have to be extra careful with the long term effects. If McDavid was 32 and signed until 36, it makes more sense. You can afford that retention then because you are either entering a rebuild or maybe he'll be more affordable in his twilight years.
I still like the idea, and it works if Edmonton is all in for 4 years and prepared to start over at that point, but that's a strong determination to make before winning a cup with this group.