Last month, Nick Kypreos made a comment on Hockey Night in Canada that sent shivers down my spine by mentioning Ken Holland and Seattle in the same breath. Holland was a fantastic General Manager — in fact, one of the best — but has shown no resemblance to that in his recent years. He has yet to receive a new offer from the Detroit Red Wings ownership as his team spirals down a path of certain destruction. It would behoove Seattle, in my humble opinion, to scratch his name off the list of potential GM’s.

Detroit Red Wings General Manager Ken Holland was once considered to be the best in the business. His teams reached the playoffs for eighteen straight years and advanced to the Stanley Cup Finals four times — emerging as champions in three. The locker room housed legendary players such as Steve Yzerman, Pavel Datsyuk, Sergei Fedorov, and Chris Osgood.

Fans and opposing front-offices loved to hate them.

“I spent my 17-year career in different NHL front offices during this historic Red Wings run,” wrote Frank Provenzano in an article for the Athletic. “We would emulate Detroit. We would hate them. But we didn’t often beat them.”

It seems like yesterday that Sergei Fedorov, with his two-piece stick and white skates, was carving circles around my beloved Bruins. The reality is that his thirteen-year career with the Red Wings ended a decade and a half ago and those dominant years in Detroit are only visible in the rear-view mirror.

Last year, they missed the playoffs for the first time since 1989.

Any fan of the game understands that you can’t stay on top forever and that with regression comes rebuild. It’s an ebb and flow that drives our emotions and encourages a love-hate relationship with front-offices.

Photo by Gregory Shamus/Getty Images

Teams in “rebuild mode” will generally drop the contracts of older players by trading them away for young prospects and draft picks. As their talent drops, so does the teams place in the standings — increasing their chances of gaining higher picks in the Entry Draft lottery.

Ken Holland seems to have missed the memo.

The Red Wings currently have 10 players with no-trade clauses, all of which are assigned to skaters over the age of 27.

Additionally, four players over the age of 30 have contracts which extend to at least the 2020-21 season.

CapFriendly.com

The destruction isn’t all on the hands of Holland — he has after all attempted to right the ship over the last couple of years — but he played a major role in handcuffing the franchise with bad contracts and a limited prospect pool.

“Denial is a powerful thing. It kept the Detroit Red Wings in the playoff picture for an astonishing 25 consecutive seasons,” wrote Matt Larkin of the Hockey News. “Now it threatens to bind their feet in cement for years to come. The Wings’ post-season streak finally ended in 2016-17, but GM Ken Holland remains committed to keeping his team competitive in the present.”

The first few years will be challenging for Seattle and they need to have someone at the helm who can build prospect depth and handle contracts with the future in mind. I would be very hesitant to say that Holland fits that bill.

“Let’s make no mistake about it, Kenny Holland is out there,” Kypreos said on Hockey Night in Canada. “His contract is going to expire at the end of the year. No talks at all scheduled. It appears it might go all the way to the end of the season before it gets addressed. You’ve got to put him at the top of the list.”

While being a GM concerns a lot more than just contracts, it’s the on ice results that matter and Ken Holland is failing his team in that category.