Win a Stanley Cup or Miss The Postseason…Which One Happens First?

After the Pittsburgh Penguins locked up their fourth Stanley Cup championship in franchise history on Sunday night, it was hard not to watch the trophy presentation and players taking turns hoisting the hardware without thinking ‘How long until the Red Wings return to glory?’

Sadly, it could be later rather than sooner and the status of the organization may get worse before it gets better. So I ask the question, which happens first: the Wings miss the postseason or win a Stanley Cup? The 2016 offseason will determine which direction the Wings are heading in.

Still adjusting to the NHL’s salary cap era — established 12 years ago, before the 2004-05 season — general manager Ken Holland has struggled more recently with bad free agent signings like former Red Wing Stephen Weiss and an ineffective Brad Richards last season. Even worse are the long-term, virtually immovable contracts given to goaltender Jimmy Howard and defenseman Jonathan Ericsson.

Factor in the potential dead money cap hit of a still undecided Pavel Datsyuk and the status of this team looks grim in terms of player personnel as well as available funds to work with.

Don’t expect a quick fix to this roster during the NHL offseason. The best-case scenario would be…

  1. Getting out from under Howard’s $5.5 million cap hit
  2. Trading Datsyuk’s $7.5 million in dead money
  3. Blockbuster free agent signings in…
    • Superstar goal scorer Steven Stamkos
    • And/or shut-down defenseman Keith Yandle

…The problem with this? Holland would be fortunate to pull off just one of these offseason moves, let alone all four. Howard’s contract conundrum is the lack of a market for goaltenders around the league. The only potential landing spots for him would be Carolina or Calgary and the Wings would most likely have to add a prospect or two in order for the Hurricanes or Flames to entertain the proposal.

Maybe Datsyuk returns. Maybe. Even if he does, a would-be 38-year-old Magic Man is a shell of his former self after failing to reach 50 points last season. He cannot be counted on to carry the bulk of the offensive responsibilities especially at that asking price, so Datsyuk leaving to Russia — along with his contract to say, Arizona or New Jersey — would free up much-needed money for free agency.

Don’t expect a blockbuster free agent to find his way to Detroit either. Forget about Stamkos, if he doesn’t return to Tampa Bay and Steve Yzerman, he’ll go home to Toronto where the Maple Leafs can offer him promising prospects, the best hockey coach in the world and a fat contract.

While the Wings defensive corps is in dire straits and in need of a big name, it just doesn’t seem feasible. Niklas Kronwall and Mike Green make $5.5 million and $6 million respectively. Add in Ericsson’s $4 million and the impending re-signing of Danny DeKeyser, the Wings simply cannot afford to pay a fifth defenseman like Yandle, who made $5.25 million last season. So with potentially $20 miller per year invested in the top four defensemen Kronwall, Green, Ericsson and DeKeyser, only subtle improvements can be made to the back end like promoting D-men from the Grand Rapids Griffins.

Unless Holland works some serious draft-day magic like we’ve never seen him do before, this offseason could prove to be relatively uneventful. And thus, leaving the Wings much, much closer to missing the postseason in the near future than returning the Stanley Cup back to Hockeytown. What happens in the next few months will certainly determine the fate of Holland’s future as well as dictating the Wings’ immediate and future success.