The 2020 NHL Trade Deadline found the Edmonton Oilers in unfamiliar territory. Despite having the services of superstar Connor McDavid for several seasons, they had only been in contention once, in 2016-17. This time around they were above .500, in and out of first in the Pacific Division, and an Oiler not named McDavid was leading the scoring race. The time had come, it seemed, to mortgage a bit of the future in order to add depth and truculence for a playoff run.

Holland Was Always Going to Be An Improvement Over Chiarelli

Peter Chiarelli, the general manager back in 2017, hadn’t really known what to do when the deadline arrived. He didn’t have the confidence to double down on a somewhat competitive roster and the only additional player he added was undersized, and fading, David Desharnais. And while Desharnais did score an important goal in that run, the team could have benefited from help on the back end, especially after top-four d-man Andrej Sekera went down.

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This time, Ken Holland, the long-time and highly successful general manager of the Detroit Red Wings, was at the helm. While Edmonton fans were understandably gun shy, given the debacle that was the Chiarelli era, there was hope that Holland would do what needed to be done without destroying the future of this competitive window that seemed to be opening up. He’d already exceeded expectations when he managed to move out Milan Lucic during the previous offseason.

Leading up to and during the course of deadline day, Holland had seemed to address a number of issues with the Oiler lineup. Mike Green was acquired in exchange for Kyle Brodziak, who hadn’t played a game during the season, and a conditional fourth-round pick. While Green wasn’t putting up the Paul Coffey-esque numbers he once did, it looked like a significant addition to a defensive core that often struggled to aid the forwards in the other team’s zone.

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Following the Green pick up, Holland made a splash with a second trade with the Red Wings. Andreas Athanasiou, a former 30-goal scorer, came in with Sam Gagner going the other way along with two second-round picks. Along with Athanasiou, the Oilers got prospect Ryan Kuffner, who appeared in 10 games the year prior with the Wings, to little effect. Barely half an hour after the Athanasiou pick up, hometown boy Tyler Ennis was acquired in exchange for a fifth-round pick.

Early Opinions Gave Holland High Marks

At the time, it looked like the Oilers had a great day. Holland had added both depth and offence. While none of the day’s biggest names came to Edmonton, they also had given up relatively little and looked poised to make a run. Though question marks remained on the back end, the team looked like it could continue to outscore any defensive issues and certainly win a round or two. But that wasn’t how things turned out.

Green’s Oiler career was a short one. Falling injured after less than a week as an Oiler, he made no impact on the regular season and, in spite of time to recover due to the pandemic shutdown, Green elected to retire. The good news is, the conditions on the draft pick Holland gave up would never be met. It solidified as a fourth-round selection in this year’s draft.

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Athanasiou showed flashes, both in what remained of the regular season, and in the preliminary play-in round versus the Chicago Blackhawks, but did not shoot the lights out at any point. His speed looks promising and one doesn’t score 30 goals at the pro level without some skill, but as a restricted free agent, it will be interesting to see how Holland handles the negotiation, especially with his team already near the cap. Between buyout dollars remaining and bonus overages, the Oilers have cap space lower than many other teams as it is.

Tyler Ennis, Arguably the Best Acquisition of the Day

Ennis was a pleasant surprise. Able to play up and down the lineup, he seemed like the sort of depth player that top teams always seem to be able to find. With four points in three preliminary games, he was one of the few Oilers not named McDavid or Draisatl to contribute versus the Blackhawks. Fate is cruel though and an awkward collision with Kirby Dach put Ennis out, the Oilers playing only one more game without him before bowing out of the 2019-20 season for good.

So how did Holland do in the end? Four draft picks given away, one for each post-season game the Oilers took part in. Of the players who left in February, only Sam Gagner might have added something. Though suggesting it would have been more than Ennis is a stretch. So the roster was slightly improved, at the cost of numerous future draft picks. We won’t know for years what the actual cost of these trades is, but NHL-calibre players come out of the second round on a regular basis.

Hopefully, Ennis fully recovers, Holland re-signs Athanasiou, and both become regular contributors on a competent Oiler team next season. That would move the needle further in the Oilers favour when we next look back on these trades. For now, there’s plenty of good hockey being played in Edmonton, just not by the orange and blue.

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