There have been a plethora of general managers (GM) at the helm over the last several years for the Edmonton Oilers on trade deadline day. With a GM who owns a large and experienced resume like Ken Holland, who is entering his second year working the phones, the Oilers are looking like buyers, although any possible deal will have to be a dollar-in, dollar-out transaction. This year has provided the team with a unique opportunity to make a deeper run in the playoffs because of how the playoff format is set up, and should make for a much more active trade deadline this year than the organization has had in the past.
2020 Trade Deadline: Feb. 24, 2020
This deadline was the first one the team has gone through with Holland, and the main acquisitions came in deals from Holland’s former team in the Detroit Red Wings. The team attempted to shore up their blue line by acquiring Mike Green for now-retired center Kyle Brodziak and a conditional third. This deal did not work in the Oilers’ favor as Green would only play two games before going down with a knee injury that would see him sit out the rest of the team’s season.
Another significant deal the team made this year was the Andreas Athanasiou experiment. The Oilers brought the speedy winger in along with Ryan Kuffner (now playing in the German League) in exchange for veteran Sam Gagner and a pair of second-round picks in 2020 and 2021. Athanasiou saw time with Connor McDavid in the hopes that his speed would be able to match that of McDavid to form a high-paced, high-scoring line.
Related: 2021 Trade Deadline Tracker
Unfortunately, Athanasiou only tallied two points in his nine regular-season games played and zero in his four playoff games, before leaving in the offseason to join the Los Angeles Kings. Two second-round picks is a steep price to pay for a restricted free agent forward who was let go in the offseason and leaves the team feeling the repercussions with even less draft capital at their disposal.
The last deal of significance that was made on this day was the acquisition of hometown forward Tyler Ennis from the Ottawa Senators for a 2021 fifth-round pick. Although the Oilers had to give up another future draft pick in this deal, Ennis was re-signed in 2020 Free Agency on a one-year deal worth $1 million. He has provided depth scoring for the Oilers since he was acquired, including nine points through 27 games this season.
2019 Trade Deadline: Feb. 25, 2019
This trade deadline was very uneventful, which could have been because it took place almost a month after the Oilers had fired GM Peter Chiarelli. The Oilers promoted Keith Gretzky as the interim GM, who was responsible for a few transactions on the final day of dealing.
The organization was in somewhat of a selling stage considering they were not really in the mix for a playoff spot this season and were focused on acquiring some assets for pending free agents. The biggest move Gretzky made was sending pending unrestricted free agent goaltender Cam Talbot to the Philadelphia Flyers in exchange for Anthony Stolarz. Talbot, who played four seasons for the Oilers, went 104-95-19 with a 2.47 goals-against average and .914 save percentage in 227 games with the team, while Stolarz went on to play only six games for the team before signing with the Anaheim Ducks in the offseason.
The team also acquired veteran Sam Gagner from the Vancouver Canucks in exchange for Ryan Spooner. This acquisition was one that was likely made to provide leadership in a young locker room. Gagner notched 10 points in the remainder of the 2018-19 season and another 12 points in 36 games a season later before he was moved to Detroit as previously mentioned at the 2020 Deadline. These deals were ones that did not have any significant impact on shaping the future of the team besides some intangible benefits gained from bringing a veteran like him into the fold.
2018 Trade Deadline: Feb. 26, 2018
Heading into the deadline in 2018, GM Chiarelli made a few moves prior, but only one on the trade deadline day. The Oilers moved on from big-bodied winger Pat Maroon, sending him to the New Jersey Devils in exchange for prospect J.D. Dudek and a third-round pick.
Maroon had played a big role on the team’s top-line alongside McDavid after being acquired from the Ducks in the 2015-16 season. Through his career as an Oiler, Maroon played in 167 games putting up 52 goals and 94 points across the regular season and playoffs. Although he did not win the Cup with the Devils after he was moved at the deadline, Maroon would go on to win back-to-back Stanley Cups in 2019 and 2020.
Dudek never ended up playing a game for the Oilers organization and is currently playing in Sweden. Fortunately, the deal wasn’t a complete bust considering the team traded their third-round pick acquired in the deal to the Philadelphia Flyers in exchange for Cooper Marody.
The 24-year-old forward has only played six games at the NHL level for the Oilers in the 2018-19 season without registering a point, but has been solid for the Bakersfield Condors in the AHL for the last three seasons, including posting 25 points in 22 games this season. He is knocking on the door for an NHL role.
2017 Trade Deadline: March 1, 2017
Considering how successful the Oilers were in the regular season, finishing with a 47-26-9 record, they were not active on deadline day. Besides a minor league player transaction that saw them acquire Justin Fontaine for Taylor Beck, there were no moves made to bolster the team for a Cup run.
Related: Oilers Should Add Hall or Hoffman
Center David Desharnais was acquired a few days prior to the deadline, but that is far from a pivotal move to make a serious run. The team was bounced in Round 2 of the playoffs by the Ducks.
2016 Trade Deadline: Feb. 29, 2016
This deadline day was a busier one by the Oilers standards and significant moves were made. This is the year Chiarelli went out and acquired Maroon from the Ducks, which proved to be worth the fourth-round pick and prospect Martin Gernat that the Oilers gave up to acquire his services, considering Maroon remained with the team for three seasons and one playoff run. The team also gave up Justin Schultz a few days prior to deadline day to the Pittsburgh Penguins for a third-round selection in 2016.
The third-round pick was used to select defenseman Filip Berglund in the 2016 NHL Entry Draft. While Schultz has gone on to have success on other teams, Berglund is still only 23 years old and under contract with the Oilers. He is currently on loan in Sweden and, although has yet to play a game in North America, could make his way over soon.
2015 Trade Deadline: March 2, 2015
This was the year Craig MacTavish was at the helm as the GM of the team and would be replaced by Chiarelli at the end of the season. Before he was relieved of his duties, MacTavish pulled off the only deadline day deal for the Oilers that season and it has had significant impacts on the team even today.
The team traded defenseman Jeff Petry to the Montreal Canadiens for a second-round pick and a conditional fifth-round pick both in the 2015 Draft. At first glance, this deal may look like a loss considering the success Petry has gone on to have for the Canadiens, but the draft picks were used efficiently and have helped the team in different ways.
The Oilers used the second-round pick as part of the package to acquire Cam Talbot who did help solidify the team’s crease for several seasons, including a second-round playoff appearance. The pick went on to be used by the Washington Capitals to select defenseman Jonas Siegenthaler 57th overall. The conditions on the fifth-round pick were also met and the team used the pick to select defenseman Caleb Jones 117th overall. Jones is still a member of the organization and has seen a total of 81 games at the NHL level in his third season with the team, and has the ability to be a solid bottom-four defenseman.
Sizing Up the 2021 Deadline
With the Oilers not having to play across different divisions or conferences until after the second round of the playoffs this year, there is a unique opportunity for the team to take advantage of the situation and be buyers come the 2021 Trade Deadline. The organization does have some obstacles to overcome if they want to add assets, such as limited draft capital for this season and extremely limited cap space, meaning Holland will need to get creative in order to make any notable additions to the lineup.
With an experienced manager like Holland who is used to being active at the deadline from his days with the Red Wings, there is optimism that the team will make some moves to add to their roster in an attempt to make a Cup run.
I am a graduate of Seneca Colleges Civil Engineering Technology Program and have turned my obsession for sports into a lifestyle. I cover the Edmonton Oilers here on The Hockey Writers but have been a diehard Maple Leafs fan since birth. Fantasy sports is more than just a hobby for me it’s a passion. I’m always looking for the next best sleeper pick or blockbuster trade. I love collecting sports memorabilia and when I’m not watching the Toronto Raptors, Blue Jays, or Pittsburgh Steelers; you can find me playing for my ball hockey team, playing video games, or listening to classic rock with a cold one or a coffee in my hand.