Do I think it's time? Yes. Do the people that matter think it's time? No.
What I do find interesting is that Nill and Yzerman haven't followed the Holland mould entirely. Yzerman just cleaned a bunch of fat from his roster, had no problem shipping off Conacher for Bishop right after Cory had a breakout year, and got solid value for MSL. Nill has made 2 big trades in consecutive years.
Now, are they in different positions than Holland with respect to their organizations? In the past, definitely. But now? I'm not so sure. Now is the time for Holland to get creative or move outside his comfort zone and yet here he is pulling the same old moves. Both clubs are getting creative so that they may progress; Holland has watched his club decline and stagnate at best.
All this makes me wonder why it is that Hollands two protégés have been so bold. Obviously there's plenty to learn from Holland, but they've surpassed him at least in ingenuity, which IMO, is one of the most important virtues in the cap world. They don't have the resume that Holland does, but will anyone ever have a resume like that in the cap world again? Probably not. Part of me wonders if Holland is surrounded by a substantial number of yes men or whether he even considers bold, roster-altering moves that might be suggested to him.
Either way, Holland is stale in today's world.
It's just not fair to compare Holland situation against Yzerman/Nill -situations. They got crap teams with high picks without a strong core, and they have been aggressive to acquire one. Lots of cap space to make UFA splashes, and then trade other asset, at least Yzerman is clearly using that GM book. Looks like Nill also. So far, during his 4 seasons, Yzerman has won 2 playoff-series at 2011 he called pure luck because of other teams injuries (Pens had both Malkin and Crosby out against them etc.). Other 2 years have been out of the playoffs and last year 1st round exit sweep. Still long way to go at Tampa. It not reasonable to judge Nill yet, just too early for a GM job. Let's see where they are after 4-5 years.
We have had that strong core already at Datsyuk/Zetterberg/Lidström/Kronwall, so you kind of have to be stale and go with them, because they are the stars and that center duo is still one of the best what you can get in NHL. I'm quite sure Nill and Yzerman would have kept both also.
I'd like to see Yzerman and Nill after few Cups and long-term success how they operate. They operate now like Holland operated on his first years. Aggressive, burning assets. The manager "game" changes totally after success. It's the hardest years you can ever live as a GM. Years after success.
For example, it will be Interesting to see how great GM Stan Bowman will be, when those 10M contracts will hit for Toews and Kane...?
Only GM who really has done just hand down supreme overall job at recent years have been Dean Lombardi. Rebuilded the Kings through high picks, drafted great for every possible position and has made phenomenal great trades and have had superb cap management. No weaknesses on his perfect team and their drafting system is still producing talent.