Ken Holland has put the Detroit Red Wings in a precarious situation. The worst thing that can happen to a team is wallowing in mediocrity for years on end. All he needs to do is ask the Detroit Pistons, who he shares an arena with, about that. However, Holland doesn't believe in full rebuilds, and he never has. With that being said, rebuild or no rebuild, not moving Mike Green before Monday's trade deadline is a monumental failure, and a testament to past mistakes.

The Red Wings were baited into a no-trade clause for Green before the 2015 season. After seasons in which the former Norris and Hart Trophy contender played 49, 32 and 35 games, he bounced back to play 70 and 72 in his final two years with the Capitals. Green has been relatively healthy in Detroit, he just hasn't played well. His +/- with the Red Wings has been -34, and he's never been above 0.

With all of that in mind, it makes sense that Green was on the trading block. Green, however, only agreed to waive his no-trade clause for the Lightning and Capitals. Unfortunately for the Red Wings, Ryan McDonagh and Erik Karlsson were also on the block, two defensemen who are demonstrably better than Green, not to mention captains of their teams. Green has also been battling a neck injury that he suffered a few weeks ago, which stunted interest in him. The only draw Green had over McDonagh and Karlsson was that the Lightning and Caps would only be competing with each other.

Both teams had their eyes on bigger prizes. McDonagh went to the Lightning, while the Capitals were reportedly in talks for Karlsson and stayed put after the deal fell apart. The Golden Knights were also in talks for Karlsson, and when those talks fell through, the Red Wings and Golden Knights both got consolation prizes: The Wings got this year's first, next year's second and 2020's third from the Knights, whereas the Knights got winger Tomas Tatar. It was a decent deal for both teams -- the Knights get an average to good scorer while the Red Wings got a significant pick package -- but it wasn't the golden goose. Gustav Nyquist was also on the block, but he had a no-trade clause of his own.

All of these contracts -- and the difficulty in moving them -- are a part of Holland's loyalty graveyard. Why would Nyquist have an NTC? Why would Tatar be making over $5 million a year? The reason is the Red Wings' penchant for remaining loyal to players raised within the system. Which is great -- to an extent. Now, massive contracts to Henrik Zetterberg, Frans Nielsen, Darren Helm, Justin Abdelkader and Jimmy Howard are taking major tolls on the Wings' cap situation. Daniel Cleary's contract back in 2014 is another infamous example.

Red Wings fans are noticeably disgruntled about the deadline moves -- or lack thereof. Holland's utter refusal to commit to a rebuild has rubbed the fan base the wrong way for years, with some not being fans of the insistence on keeping the Wings' 25-year playoff streak alive when it clearly wouldn't result in a championship. When that was snapped, it was thought the team would lean into the rebuild more -- apparently wrongly. The Red Wings now sit in no-mans-land, five points out of a wild-card spot but nowhere near the worst in the league. Not moving Green, however, feels like a huge loss for a front office that has taken a few of those lately.

Green has expressed interest in re-signing with the Wings when his contract is up after this season. He's having a bit of a resurgence this year, which added value to him as a trade piece. However, he won't be the difference in the Wings winning a Cup.

Detroit needs to find the guy that will be, and it's trying to accumulate the resources to do it. At this moment, it has 11 picks in the 2018 draft. Two first-rounders (one of which will be a late pick because it is coming from Vegas), two second-rounders, two third-rounders, two fourth-rounders, two sixth-rounders and a seventh. One of the fourths could turn into a second or third depending on how the Flyers round out the season. With that in mind, the Wings have a lot of work to do, and a lot of pieces to get it done. But they need to do it right from here on out.

Whether or not Holland likes it, the Wings will have to rebuild. That may be through taking lumps next season in 2018 or a multi-year project, but they simply don't have the assets right now to make a run. The Red Wings finally throwing in the towel on Petr Mrazek by trading him to the Flyers seemed like it might be a step towards acceptance, but they're trying to tiptoe around what it will actually need to be.

And then, there's the elephant in the room: Holland's contract expires after the season. As of now, it seems impossible that he'll get extended. Yes, Holland is a four-time Stanley Cup winner and yes, he should be celebrated. But he isn't getting it done right now, and no one needs to be reminded that this is a "what have you done for me lately" league. If Holland leaves, coach Jeff Blashill is likely to go with him, as GMs generally like to bring in their own guys.

As for who that new GM would be? If the Red Wings want to promote from within, former player and current assistant to the general manager Kris Draper would be the logical decision. Assistant general manager Ryan Martin may be on that list as well. With that being said, Red Wings fans know more than anyone about the dangers of staying too loyal. If the Red Wings are serious about winning, they may want to look outside of their organization. Perhaps an assistant GM from a team where rebuilds worked, e.g. the Maple Leafs or the Jets. Perhaps even the Stars. 

It's a delicate situation, and it's especially difficult with how far back Holland goes in the organization. Even if he did lose his GM role, he'd likely stay on as an adviser. However, not moving Green isn't the problem. At least, not the clear and present one. Not even being able to is. The Red Wings are loaded with brutal contracts, and they need to accept with those in place, they likely won't contend. To be blunt: 2021 looks like the first year that the Wings can really start making runs again without some major shakeups and salary dumping. Zetterberg, Glendening and Helm all come off the books that year, with some of the other major ones coming off in years prior. Until then the Wings just need to keep stockpiling picks and keeping an eye on their years with the Griffins to see who will be ready when their number is called (while shopping those contracts as they get closer to their expiration dates).

For what it's worth, it isn't all doom-and-gloom. The Red Wings have a deep bench of prospects. Tyler Bertuzzi, Evgeny Svechnikov, Filip Hronek and Dominic Turgeon have all generated buzz, alongside goalie Matej Machovsky, who has impressed in his first few games. However, none of that will matter if the Wings don't land on picks. Trading for every pick in the draft won't matter if none of them pan out. The likely next step is finding a GM that will ensure that they do.

Fans appreciate loyalty to players that bring home championships. No one would have had a problem with paying Steve Yzerman forever, and the Zetterberg contract's blow is lessened by his 2008 championship. However, to many fans, Green still being a Red Wing will likely be the last straw. It's a failure to do something that needed to be done -- something that many Detroit fans are too accustomed to seeing.