Last week, I looked at Ken Holland’s best moves in Detroit. Holland had a Hall of Fame run in Detroit. He won three Stanley Cups over 22 years as Detroit’s general manager. Holland had a ton of success, but that wasn’t without mistakes along the way. Trying to prolong a legendary playoff streak comes with consequences. Detroit finally accepted their need to rebuild, but it didn’t come before some poor decisions. I’m only including moves in the salary-cap era because Holland won’t have the same luxury as Oilers GM.

Big contracts to veterans

Holland will be familiar with Edmonton’s difficult cap situation because Detroit is in a similar position. Holland gave long-term deals to Justin Abdelkader, Darren Helm, Frans Nielsen, Danny DeKeyser, Jonathan Ericsson, Johan Franzen, and Stephen Weiss.
The Weiss contract was one of Holland’s worst transactions. Detroit bought out Weiss out just two years into his five-year contract. Holland gave Weiss $4.9 million per year. Weiss scored 29 points in 79 career games with the Red Wings.
Abdelkader got seven years at $4.25 million after a couple of 40-point seasons riding shotgun with Pavel Datsyuk and Henrik Zetterberg. Abdelkader hasn’t scored more than 35 points three years into the contract.
Nielsen and Helm were part of the group that received giant contracts given in free agency on July 1st, 2016. Nielsen might be the best of the bunch. Troy Brouwer’s already been bought out. David Backes is routinely healthy scratched. Holland will be tasked with ridding the Oilers of Milan Lucic’s contract.

The Kyle Quincey ordeal

You’re bound to hear a bunch about development and ‘overripening’ prospects with Holland as Oilers general manager. Giving prospects a bunch of time in the minors isn’t a bad thing. The Oilers have rushed too many players, but not playing players when they’re ready means you don’t know what you have. Sometimes you lose those players on waivers trying to sneak them to the minors like Detroit did with defenceman Kyle Quincey in 2008. Quincey played 21 minutes a night and scored 38 points for Los Angeles that season.
Giving away a top-four defenceman on waivers hurts. Trading a first-round draft pick for that same defenceman four years later hurts a little more. Quincey was just 26 and would play 250 games for Detroit in a top-four role before being shipped to New Jersey at the deadline in 2017.
Oh, and the first-round pick the Red Wings sent to the Lightning for Quincey was used on goalie Andrei Vasilevskiy.

Deadline deals

Holland’s moved solid prospects for aging veterans, which is standard good teams at the trade deadline.
Holland traded center Calle Jarnkrok, a 2014 second-round pick, and Patrick Eaves to Nashville for David Legwand. Legwand had 11 points in 22 games down the stretch with Detroit and zero points in five playoff games.
Holland traded Mattias Janmark, Mattias Backman, and a 2015 second-round pick to Dallas for Erik Cole. Cole had 6 points in 11 games before going down with a season-ending spine injury.
Jarnkrok and Janmark aren’t world beaters, but they’re solid middle-six guys on cheap contracts. Replace Abdelkader and Helm with Janrkrok and Janmark and suddenly you have a ton of cap space to use.