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Ken Holland At The Trade Deadline

The Edmonton Oilers, if they do anything, will be buying at the upcoming NHL trade deadline. The club currently sits in first place in the Pacific Division and is in a good spot to make the 2020 Stanley Cup Playoffs. The Oilers haven’t been a buyer at the deadline since 2017, when they traded for David Desharnais.

That was Peter Chiarelli’s second deadline at the helm in Edmonton. In Chiarelli’s first go-around, he dumped Justin Schultz and Teddy Purcell for picks, then went out and bought Pat Maroon. It was a solid day of work that also included the waiver claims of Adam Pardy and Adam Clendening on defense along with Adam Cracknell up front.

This is Ken Holland’s first deadline as GM of the Edmonton Oilers. It will be vastly different than Chiarelli’s. Holland will not be selling off assets, that we know for sure. After all, his most valuable pending UFA (Zack Kassian) and RFA (Darnell Nurse) have already signed extensions with the club.

If anything, Holland will add to the stable.

The best way to predict future events? Take a look back at the past. That is exactly what we will do today. Let’s take a look back at Ken Holland’s recent trade deadlines as GM of the Detroit Red Wings.

This will show us how Holland handles being the GM of a seller, contending buyer and buyer trying to push to make the playoffs.


The rebuild was officially on in Detroit, and Holland made two moves at the deadline. He shipped out pending UFA’s Gustav Nyquist and Nick Jensen, acquiring futures for the Red Wings organization.

To San Jose: Gustav Nyquist
To Detroit: 2019 2nd round pick (Albert Johansson), 2020 conditional 3rd round pick

To Washington: Nick Jensen, 2019 5th round pick (Traded to New Jersey)
To Detroit: 2020 2nd round pick, Madison Bowey

Overall, Holland did well here. Bowey is a decent young NHL defenseman, while he also acquired two picks in a loaded 2020 entry draft.


The Red Wings also sold in 2018, making one deal on deadline day and another a week prior. Again, nothing too earth shattering but the Red Wings did move a player that has turned into a strong option in Tomas Tatar. That said, at the time, Holland got good value here.

To Vegas: Tomas Tatar
To Detroit: 2018 1st round pick (Joe Veleno), 2019 2nd round pick (Robert Mastrosimone), 2021 3rd round pick

To Philadelphia: Petr Mrazek
To Detroit: 2018 conditional 4th round pick, 2019 conditional 3rd round pick


Holland was in a different position than ever before at this deadline. It was the first time he was truly a seller. The Red Wings were an older team and their lengthy playoff streak was clearly coming to an end. The club elected to finally give in and begin the long overdue rebuild.

Holland made four trades during deadline season this year, effectively ending an era in Michigan.

To Montreal: Steve Ott
To Detroit: 2018 6th round pick (traded to Columbus)

To Florida: Thomas Vanek
To Detroit: Dylan McIlrath, 2017 3rd round pick (Kasper Kotkansalo)

To New York (Rangers): Brendan Smith
To Detroit: 2017 3rd round pick (Zachary Gallant), 2018 2nd round pick (Jonatan Berggren)

To Chicago: Tomas Jurco
To Detroit: 2017 3rd round pick (Keith Petruzzelli)


The last time Ken Holland oversaw a playoff team was the 2015-16 season. The Red Wings finished 3rd in the Atlantic Division and took on the Tampa Bay Lightning in the first round. The Bolts easily handled the Wings in five games. An older Detroit team was clearly no longer a Stanley Cup threat, and Holland treated it as such at the deadline.

Instead of pushing his chips in the middle and buying a piece or two, Holland elected to essentially stand pat.

To Florida: Jakub Kindl
To Detroit: 2017 6th round pick (Reilly Webb)


2015 was truly the last time Holland was a buyer at the trade deadline. Although the Red Wings were clearly at the end of their lengthy competitive cycle, Holland was willing to augment a core that included Pavel Datsyuk and Henrik Zetterberg.

He actually fared quite well with the addition of Marek Zidlicky, who collected eleven points (3-8-11) in 21 games after the trade.

Holland also acquired Erik Cole (3-3-6, 11 GP) from Dallas. Cole did not play in the postseason and retired after the campaign due to a spinal contusion.

In the end, Detroit would bow out to the Tampa Bay Lightning in six games.

To Detroit: Marek Zidlicky
To New Jersey: 2016 conditional 3rd round pick (Traded to Pittsburgh)

To Detroit: Erik Cole, 2015 conditional 3rd round pick (Vili Saarijarvi)
To Dallas: Mattias Backman, Mattias Janmark, 2015 2nd round pick (Roope Hintz)


Holland and the Red Wings moved to the Eastern Conference for the 2013-14 season. It would be the first of three consecutive seasons where the club would be eliminated in the first round of the playoffs. This time, it would be at the hands of the defending Eastern Conference Champion Boston Bruins.

Holland was still of the belief that his team could compete. After all, the Red Wings had pushed the Chicago Blackhawks to seven games and nearly won that second round series in 2013. The dynasty Hawks would go on to win their second Cup a month later.

Holland believed, and with good reason, that his club still had it.

He pushed his chips to the middle and acquired veteran David Legwand from the Nashville Predators.

The price was dear, but Legwand was decent for the club. He scored 11 points in 21 games (4-7-11) and appeared in all five playoff games. Legwand signed with the Ottawa Senators as a free agent that summer.

To Detroit: David Legwand
To Nashville: Calle Jarnkrok, Patrick Eaves, 3rd round pick


Holland didn’t do much at the deadline in 2013. The lockout shortened campaign of just 48 games was the last time the Wings won a playoff series. They took out the Anaheim Ducks in round one before falling to the Chicago Blackhawks in seven games in round two.

Holland was confident in his group and left it as is. His only move was subtracting depth defenseman Kent Huskins.

To Philadelphia: Kent Huskins
To Detroit:2014 conditional 7th round pick


2012 was an interesting deadline for the Red Wings. Detroit was still very much an expected contender, but they ended up both selling and buying at the deadline. In all, Holland made two trades. Both involved a veteran defenseman either coming in or heading out.

The Wings finished fifth in the west that spring, falling in five games to the Nashville Predators in the first round of the playoffs.

To Tampa Bay: Mike Commodore
To Detroit: Conditional 2013 7th round pick

To Detroit: Kyle Quincey
To Tampa Bay: Sebastien Piche, 2012 1st round pick (Andrei Vasilevskiy)


Holland only made one trade during the 2011 calendar year. That was a draft day trade in Minnesota when, after the Oilers selected Oscar Klefbom, Holland moved back. Detroit sent pick 24 (Matt Puempel) to Ottawa for picks 35 (Tomas Jurco) and 48 (Xavier Ouellet).

Holland made no trades at the deadline and the Wings finished 3rd in the Western Conference, wining the Central Division. They eliminated the then Phoenix Coyotes in a sweep before falling to the San Jose Sharks in seven games in the second round.


Still very much a Cup contending team, Holland stood pat at the 2010 deadline. He made two minor trades, but allowed a team that had went to the Cup Final two years in a row to make another run.

Detroit finished fifth in the west and won their first round series in seven games over Phoenix and Dave Tippett. They’d lose in five games to San Jose in the second round.

To Calgary: Andy Delmore
To Detroit: Riley Armstrong

To New York (Rangers): Kris Newbury
To Detroit: Jordan Owens

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