On Thursday evening, the Edmonton Oilers face the Detroit Red Wings for the second time this season.

The Red Wings are currently on the up-and-up, going 11-4-1 since they hired former Edmonton Oiler coach Todd McLellan. Funnily enough, McLellan isn’t the only hockey operations member the two teams have shared, as Ken Holland has been the general manager of both teams.
With a 24-21-5 record, the Wings are just two points out of a postseason spot. They are looking to break an eight-season postseason drought, the second-longest in the league, behind only the eternally bad Buffalo Sabres.
It wasn’t always that way though, as the Detroit Red Wings made the postseason from the 1990-91 season until the 2015-16 season. That’s tied for the longest such streak in National Hockey League history, as the St. Louis Blues also had a lengthy streak.
<h2>A brief history of Ken Holland’s tenure with the Red Wings</h2>
Coming off their first Stanley Cup championship since 1954-55, the Red Wings promoted Holland from their assistant general manager to their general manager on Jul. 18, 1997. The Wings went back-to-back in the 1998 postseason and won two more Stanley Cups, one in 2002 and another six years later in 2008.
At a certain point though, Holland refused to rebuild, signed veterans to sizable contracts, whiffed on draft picks (like picking Filip Zadina one pick ahead of Quinn Hughes), and left current general manager Steve Yzerman with a mess to clean up. Funnily enough, Yzerman’s final game in the league was against the Oilers in the 2006 postseason. Although not the main topic of <a href="https://oilersnation.com/news/throwback-thursday-how-a-trade-with-the-wild-in-2005-06-helped-the-oilers-reach-the-stanley-cup-final">this Throwback Thursday</a>, that series was covered in it.
<div class="jetpack-video-wrapper"><iframe loading="lazy" title="ales hemsky winning goal 1st round 2006" width="1333" height="1000" src="https://www.youtube.com/embed/BsohaMrhKw0?start=33&#038;feature=oembed" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe></div>
Anyway, Holland departed the Red Wings in May 2019, signing with the Oilers for five years as their general manager and president of hockey operations.
<h2>The Peter Chiarelli era</h2>
Before Holland was Peter Chiarelli, who was hired shortly before the Oilers drafted Connor McDavid. Aside from one postseason appearance in McDavid’s sophomore season, Chiarelli’s reign was of the variety you can use numerous expletives. Simply put, it was a dark period in the Oilers’ history.
A big reason for this was some pretty devastating trades. On Jun. 29, the Oilers traded away their 2010 first-overall pick for Adam Larsson. Hall went on to win the 2017-18 Hart Memorial Trophy, but at the time, this trade made sense. A hot take of mine is that this wasn’t that bad of a trade considering their only right-shot defenceman was Eric Gryba.
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
Trade is one for one: Adam Larsson for Taylor Hall.
&mdash; Bob McKenzie (@TSNBobMcKenzie) <a href="https://twitter.com/TSNBobMcKenzie/status/748238297273610240?ref_src=twsrc%5Etfw">June 29, 2016</a></blockquote>
<script async src="https://platform.twitter.com/widgets.js" charset="utf-8"></script>
Three days prior was one of Chiarelli’s worst trades of his tenure, as he moved the 16th overall pick and 33rd overall pick to the New York Islanders for defence prospect Griffin Reinhart. The 2015 draft was one of the deepest in recent memory, and the Oilers would’ve been able to pick two really good players.
There were a few other terrible trades, and a few minor wins (Ben Scrivens for Zack Kassian), but a trade that really hurt was trading Jordan Eberle for Ryan Strome. Eberle had been in the organization since 2008 and was a fan-favourite, but he failed to produce in the 2017 draft and the Oilers preemptively wanted to create some cap space.
Strome wasn’t a bad player for the Oilers by any means, scoring 13 goals and 34 points in 82 games in 2017-18, a perfectly acceptable total for a third-line right-shot centre. However, he only scored a goal and two assists in 18 games before Chiarelli shipped him off to the New York Rangers for Ryan Spooner. In the remaining 63 games, Strome scored 18 goals and 33 points, followed by a career-best 18-goal, 59-point season in 2019-20.
The Spooner trade was Chiarelli’s fourth-last trade with the organization, as they thankfully fired him on Jan. 22, 2019. Taking over for the rest of the season before Holland arrived was Keith Gretzky, who traded Spooner to the Vancouver Canucks for another fan-favourite, Sam Gagner.
<h2>The two trades with the Red Wings</h2>
Holland’s first trade was getting <a href="https://oilersnation.com/news/report-milan-lucic-traded-to-the-flames-for-james-neal">Milan Lucic’s contract off the books</a>, trading him to the Calgary Flames for James Neal. Aside from that, there were no other major trades until the 2020 deadline, when the Oilers sent a 2021 fifth-round pick to the Ottawa Senators. The other two moves were with the team he once oversaw, the Red Wings.
First up, he moved veteran Kyle Brodizak and a 2020 conditional fourth for right-shot defenceman <a href="https://oilersnation.com/news/edmonton-oilers-acquire-mike-green-from-detroit-red-wings">Mike Green</a>. The former Washington Capital was at the tail end of his career, having once scored 31 goals and 73 points in 2008-09, an insane total. Anyway, he only played two games with the Oilers before retiring, while Brodziak never played another game after the trade. That second turned out to be netminder Jan Bednář, who plays for the Red Wings ECHL team.
The other trade was far more impactful, though. On the same day, Feb. 24, the Oilers traded Gagner along with a 2020 second-rounder and 2021 second-rounder for <a href="https://oilersnation.com/news/edmonton-oilers-acquire-andreas-athanasiou-from-detroit-red-wings">Andreas Athanasiou</a>. Unfortunately, we had a global pandemic and the 2019-20 season was cut short, with Athanasiou only playing nine regular season games with the Oilers, scoring a goal and two points. In the postseason, he played four games and was held pointless. After the season ended, he wasn’t tendered and he signed with the Los Angeles Kings.
Speaking of the Kings, they traded up for the 2020 second-round pick that turned out to be the 45th overall. The Red Wings received the 51st overall pick (Theodor Niederbach) and the 97th overall pick (Sam Stange). With the 45th overall pick, the Kings selected Brock Faber, who they eventually traded for Kevin Fiala.
The Red Wings also traded the Oilers’ second-round pick in the 2021 draft, moving it and Richard Panik to the New York Islanders for Nick Leddy. Before the trade deadline, they traded Leddy to the St. Louis Blues for Jake Walman, a 2023 second-round pick, and Oskar Sunqvist. Don’t ask a Red Wing fan what they traded Walman for.
In the end, the two trades at the 2020 trade deadline were inconsequential. The Oilers were still a couple of years away from actually contending, the Red Wings didn’t draft well, and Sam Gagner returned for his third stint before the 2023-24 season. Funnily enough, <a href="https://oilersnation.com/news/throwback-thursday-the-mark-messier-trade-tree">this trade was at the tail end of the Mark Messier trade</a>, the penultimate transaction.
<hr />
If you enjoy my content, you can follow me on Bluesky @ryleydelaney.bsky.social.

On Thursday evening, the Edmonton Oilers face the Detroit Red Wings for the second time this season.



The Red Wings are currently on the up-and-up, going 11-4-1 since they hired former Edmonton Oiler coach Todd McLellan. Funnily enough, McLellan isn’t the only hockey operations member the two teams have shared, as Ken Holland has been the general manager of both teams.

With a 24-21-5 record, the Wings are just two points out of a postseason spot. They are looking to break an eight-season postseason drought, the second-longest in the league, behind only the eternally bad Buffalo Sabres.

It wasn’t always that way though, as the Detroit Red Wings made the postseason from the 1990-91 season until the 2015-16 season. That’s tied for the longest such streak in National Hockey League history, as the St. Louis Blues also had a lengthy streak.
<h2>A brief history of Ken Holland’s tenure with the Red Wings</h2>
Coming off their first Stanley Cup championship since 1954-55, the Red Wings promoted Holland from their assistant general manager to their general manager on Jul. 18, 1997. The Wings went back-to-back in the 1998 postseason and won two more Stanley Cups, one in 2002 and another six years later in 2008.

At a certain point though, Holland refused to rebuild, signed veterans to sizable contracts, whiffed on draft picks (like picking Filip Zadina one pick ahead of Quinn Hughes), and left current general manager Steve Yzerman with a mess to clean up. Funnily enough, Yzerman’s final game in the league was against the Oilers in the 2006 postseason. Although not the main topic of <a href="https://oilersnation.com/news/throwback-thursday-how-a-trade-with-the-wild-in-2005-06-helped-the-oilers-reach-the-stanley-cup-final">this Throwback Thursday</a>, that series was covered in it.

https://www.youtube.com/watch?v=BsohaMrhKw0&amp;t=33s&amp;ab_channel=euginate13

Anyway, Holland departed the Red Wings in May 2019, signing with the Oilers for five years as their general manager and president of hockey operations.
<h2>The Peter Chiarelli era</h2>
Before Holland was Peter Chiarelli, who was hired shortly before the Oilers drafted Connor McDavid. Aside from one postseason appearance in McDavid’s sophomore season, Chiarelli’s reign was of the variety you can use numerous expletives. Simply put, it was a dark period in the Oilers’ history.

A big reason for this was some pretty devastating trades. On Jun. 29, the Oilers traded away their 2010 first-overall pick for Adam Larsson. Hall went on to win the 2017-18 Hart Memorial Trophy, but at the time, this trade made sense. A hot take of mine is that this wasn’t that bad of a trade considering their only right-shot defenceman was Eric Gryba.

https://twitter.com/TSNBobMcKenzie/status/748238297273610240

Three days prior was one of Chiarelli’s worst trades of his tenure, as he moved the 16th overall pick and 33rd overall pick to the New York Islanders for defence prospect Griffin Reinhart. The 2015 draft was one of the deepest in recent memory, and the Oilers would’ve been able to pick two really good players.

There were a few other terrible trades, and a few minor wins (Ben Scrivens for Zack Kassian), but a trade that really hurt was trading Jordan Eberle for Ryan Strome. Eberle had been in the organization since 2008 and was a fan-favourite, but he failed to produce in the 2017 draft and the Oilers preemptively wanted to create some cap space.

Strome wasn’t a bad player for the Oilers by any means, scoring 13 goals and 34 points in 82 games in 2017-18, a perfectly acceptable total for a third-line right-shot centre. However, he only scored a goal and two assists in 18 games before Chiarelli shipped him off to the New York Rangers for Ryan Spooner. In the remaining 63 games, Strome scored 18 goals and 33 points, followed by a career-best 18-goal, 59-point season in 2019-20.

The Spooner trade was Chiarelli’s fourth-last trade with the organization, as they thankfully fired him on Jan. 22, 2019. Taking over for the rest of the season before Holland arrived was Keith Gretzky, who traded Spooner to the Vancouver Canucks for another fan-favourite, Sam Gagner.
<h2>The two trades with the Red Wings</h2>
Holland’s first trade was getting <a href="https://oilersnation.com/news/report-milan-lucic-traded-to-the-flames-for-james-neal">Milan Lucic’s contract off the books</a>, trading him to the Calgary Flames for James Neal. Aside from that, there were no other major trades until the 2020 deadline, when the Oilers sent a 2021 fifth-round pick to the Ottawa Senators. The other two moves were with the team he once oversaw, the Red Wings.

First up, he moved veteran Kyle Brodizak and a 2020 conditional fourth for right-shot defenceman <a href="https://oilersnation.com/news/edmonton-oilers-acquire-mike-green-from-detroit-red-wings">Mike Green</a>. The former Washington Capital was at the tail end of his career, having once scored 31 goals and 73 points in 2008-09, an insane total. Anyway, he only played two games with the Oilers before retiring, while Brodziak never played another game after the trade. That second turned out to be netminder Jan Bednář, who plays for the Red Wings ECHL team.

The other trade was far more impactful, though. On the same day, Feb. 24, the Oilers traded Gagner along with a 2020 second-rounder and 2021 second-rounder for <a href="https://oilersnation.com/news/edmonton-oilers-acquire-andreas-athanasiou-from-detroit-red-wings">Andreas Athanasiou</a>. Unfortunately, we had a global pandemic and the 2019-20 season was cut short, with Athanasiou only playing nine regular season games with the Oilers, scoring a goal and two points. In the postseason, he played four games and was held pointless. After the season ended, he wasn’t tendered and he signed with the Los Angeles Kings.

Speaking of the Kings, they traded up for the 2020 second-round pick that turned out to be the 45th overall. The Red Wings received the 51st overall pick (Theodor Niederbach) and the 97th overall pick (Sam Stange). With the 45th overall pick, the Kings selected Brock Faber, who they eventually traded for Kevin Fiala.

The Red Wings also traded the Oilers’ second-round pick in the 2021 draft, moving it and Richard Panik to the New York Islanders for Nick Leddy. Before the trade deadline, they traded Leddy to the St. Louis Blues for Jake Walman, a 2023 second-round pick, and Oskar Sunqvist. Don’t ask a Red Wing fan what they traded Walman for.

In the end, the two trades at the 2020 trade deadline were inconsequential. The Oilers were still a couple of years away from actually contending, the Red Wings didn’t draft well, and Sam Gagner returned for his third stint before the 2023-24 season. Funnily enough, <a href="https://oilersnation.com/news/throwback-thursday-the-mark-messier-trade-tree">this trade was at the tail end of the Mark Messier trade</a>, the penultimate transaction.

<hr />

If you enjoy my content, you can follow me on Bluesky @ryleydelaney.bsky.social.

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