This is the first time in a VERY LONG time that the Detroit Red Wings likely won't find themselves playing meaningful hockey in April. The 25-year playoff streak seems to be dwindling and it's time for Ken Holland and the rest of the front office to re-structuring this team for the future. It sounds simpler than it is, but I would gut the entire roster if at all possible.
The first step: Holland needs to decide who he plans to protect for the upcoming expansion draft in June. It might be wise to leave Justin Abdelkader or Darren Helm unprotected if they can, considering both players have lots of term left on their deals at a not so favourable salary cap hit.
The next step, focus on ridding themselves of some unwanted veteran contracts (Jonathan Ericsson, Mike Green, Jimmy Howard, etc.). I would use a buyout option on Ericsson -- unless you can find someone willing to take on his contract...maybe Arizona like they did with Pavel Datsyuk? Green has one year left on his contract at a monstrous cap hit and Detroit would all but certainly need to retain some salary to alleviate some of the pressure from any trade partner. The same can be said for Howard and his ugly cap hit of over $5-million -- I would think the Wings might need to absorb nearly 50% of his salary to get anything fruitful out of the deal. Quite honestly, the Vancouver Canucks have an aging Ryan Miller and a big question mark with Jakob Markstrom in the crease, so they could very well be a suitable trade partner for Detroit to move Howard. Of course, the Dallas Stars have been rumoured to be looking for a change in net and if the Winnipeg Jets decide Connor Hellebuyck needs more development, then they too could look at Howard as an option.
Detroit also needs to explore its options with trading either Gustav Nyquist or Tomas Tatar (or both). Why not deal Nyquist before his no-trade clause kicks in and the possibility of a sign-and-trade with Anaheim to get Cam Fowler for Tatar and a pick sounds alluring -- maybe even wishful thinking.
The final step would be to bring back Thomas Vanek on a multi-year deal. Reports out of the Detroit media suggested Vanek liked playing for the Wings and his family enjoyed their time in Michigan. I think he played well on a "show me" contract this season during his time with the Wings and I think playing him in a top six role will allow a rookie like Evgeny Svechnikov to get accustomed to the NHL game before he's ready to take the next step in his progression.