It is something that can be put into serious question. It can be expanded into many senses, like what direction the team is heading in, what beholds them next season and the season after that, so on and so forth.
From the area I'm looking at, what happens to the top-six, top-2 defensive pairs and goaltending after Pavel Datsyuk, Henrik Zetterberg, Valtteri Filppula, Johan Franzen, Niklas Kronwall, Jonathan Ericsson and Jimmy Howard? The question simply remains unanswered at the moment.
There are currently no players in the organization that have proved they can fill themselves into those roles. There's no doubt that there's potential for certain players to achieve those spots from already proven play, such as Tomas Tatar, Petr Mrazek and in some ways, Gustav Nyquist. Obvious uncertainty surrounding Nyquist as he rarely gets opportunities, but that's debatable. The abilities are there for those players mentioned, but can they translate that in the NHL for a long time?
There is no clear view on what this organization relies on doing long-term for success. Do they just depend on their prospects to evolve the way their current star players have or will they look at free agency? It's pretty evident Ken Holland is not the GM that's just going to throw money at a big name in free agency just for the sake of bringing in a name. He probably had the chance to do that with Alexander Semin in the summer of 2012, but he refused to, even if it might have been worth the gamble at only one year of dealing with a $7 million contract.
If you look at the types of players the Wings have missed out on over the passed few years through free agency where Detroit basically needed a "replacement," whether it might have been acknowledging the departures of Brian Rafalski, Nicklas Lidstrom, Brad Stuart or Tomas Holmstrom, there were definitely players that raised an eyebrow. Even with that being said, there was always the risk factor, usually because of the massive contracts that were being offered on the table, such as the signings of James Wisniewski, Christian Ehrhoff, Ryan Suter and Zach Parise. All of those players who were signed over the past three years provided needs for the Wings due to key players leaving, and yes, I do firmly believe Parise was considered a need because he could have brought an element Detroit hasn't had since Marian Hossa. Not only that, you add a talented player to a lineup that will eventually be without Datsyuk one day.
Indeed, those players, with exception to Suter and Parise, have other negative factors besides their fully-loaded contracts, like Wisniewski's attitude and inappropriate gestures (hah!), and Ehrhoff's inconsistency; however, their talent is undeniable. They would have addressed needs that could have provided stability over time. I don't want to get too off-topic here, but based on passed events, Holland either doesn't seem too fond of the majority of free agents over the years or he's just waiting for the right player to pop along.
That's what it comes down to: the right players to tempt Ken Holland, specific prospects to develop into what they're expected to be or a mixture of both. Your move, Holland.