Detroit Red Wings: Breaking down the worst Ken Holland Transactions

With Ken Holland officially out of the picture in Detroit, many fans are excited to see what the future holds under the guidance of Detroit Red Wings legend Steve Yzerman, especially when you look back at some of these deals.

First, let’s talk about the current transition in the Detroit Red Wings front office and then get to the ugly transactions.  Recently the organizations long-time General Manager, Ken Holland was pushed aside in favor of Steve Yzerman.  Holland had tremendous success in Detroit being apart of four Stanley Cup Championships three of which he won serving as the teams GM.

Steve Yzerman abruptly decided to step down on the eve of training camp last September.  It was a very odd decision because the Tampa Bay Lightning were expected to be Cup contenders.  They dominated during the regular season winning 62 regular season games tying the record for all-time wins once set by the Detroit Red Wings.  The fact that the Lightning was able to win that many games in a league stocked full of parody in the cap era is nothing short of incredible.  They would go onto being shocked in the first round of the playoffs being swept by the Columbus Blue Jackets, and it was all for not.

Ken Holland recently mentioned upon signing a new five-million dollar per season deal to become the Edmonton Oilers GM and President of Hockey Operations that he knew he was in hot water in Detroit the moment Steve Yzerman stepped away from the Lightning.

The Detroit Red Wings wanted to keep Ken Holland in the organization to team up with Steve Yzerman, Pat Verbeek, and Ryan Martin to be another set of eyes.  He would have provided an abundance of experience along with a veteran perspective continuing to help the franchise turn the corner and excelling down the straightaway of the rebuild.  It became evident merely three weeks after Yzerman was introduced as the teams’ GM that Ken Holland was pushed aside and it wasn’t exactly a promotion as Chris Ilitch described it.

With Holland swiftly accepting the Oilers job, it was apparent he wanted to continue being an NHL General Manager, and we shouldn’t fault him for that.  I imagine Holland is excited to get to work trying to surround star forward Connor McDavid with talent.  But don’t kid yourself he sat down at his fancy new desk in his fancy new office with a bunch of modified “sign here” stickers beside a stack of “no-trade clause” stickers.  After scrolling through the teams’ contracts seeing Milian Lucic’s long-term (5-years remaining) expensive deal (6 million AAV) with an NTC attached he felt right at home!

In this article, I want to take a look back at some of the worst transactions Ken Holland made with the Detroit Red Wings.