With the 2024 NHL trade deadline just a week away, fans are busy making their wishlists for their teams and effigies for their GM when they don’t fulfill those wishes.
Trades on the deadline also are ones that are judged immediately as good or bad, but are also some of the only moves in the NHL calendar that can rightfully be judged only a few months later, at least when it comes to the buyer’s side. They also have a decent chance of being a win-win, given that the teams that trade with each other are not competing with each other and have different needs.
So in light of that, we thought we would revisit some of the best and worst trade deadline deals the Oilers have made.
Best: Mattias Ekholm, 2023
This is the most recent trade deadline deal done by the Oilers, and it was an absolute homerun.
The Oilers traded away Tyson Barrie to make the cap work, along with recent first-round pick Reid Schaefer, a 2023 first-round pick (who Nashville used to pick Tanner Molendyk), and 2024 fourth-round pick, in exchange for Mattias Ekholm (with $250,000 retained on his salary) and a 2024 sixth-round pick.
Ekholm had an immediate impact and is credited with settling down and boosting Evan Bouchard at even strength. The Oilers went 18–2–1 to close out the regular season after the trade and got to the second round of the playoffs, where they were ousted by the eventual Cup champion Vegas Golden Knights.
If Ekholm had been just a rental, this trade may have been looked at differently. Maybe not as bad trade, but the earlier exit than anticipated would have dulled the shine of the regular season success.
But Ekholm still had three full seasons left on his contract, which makes this deal an absolute slam dunk for the Oilers. That is two more seasons than what Barrie had on his contract, while Schaefer has struggled in the AHL this season. It’s a bit too early to make any kind of read on Molendyk on this time.
In any event, even if those two do go on to have extremely successful careers, the fact that the Oilers have Ekholm for so long during their contending window means that it is a great trade regardless.
Worst: Andreas Athanasiou, 2020
This was a trade that was either going to be considered one of the best or one of the worst, nowhere in between.
Andreas Athanasiou looked like he could be a legitimate top-six option with speed to burn, and would be a perfect fit on Connor McDavid’s wing. The season prior to the trade, Athanasiou broke out with 30 goals and 54 points in 76 games. Prior to the trade he only had 10 goals and 24 points in 46 games, on pace for 18 goals and 43 points, much more in line with his previous seasons.
Athanasiou was 26-years-old and an RFA after the season, and so it also looked like he could be a long term fit as well.
Athanasiou ended up not working out at all, finishing with just one goal and one assist in nine games prior to the COVID-19 pandemic, and followed it up with no points in the four play-in games against Chicago. The Oilers did not qualify him and he went on to be a free agent.
So it was already a bust, and then you look at what the Oilers traded for him.
In return, Detroit got Sam Gagner (for cap purposes) and two second-round picks. In a vacuum, that is a high price to pay for what ended up being essentially a warm body. Trading away a fan favourite in Gagner for what ended up being a fan the-extreme-opposite-from-favourite already makes it a terrible move.
Then you look at who ended up being picked with those second round picks: Brock Faber in 2020 and Aatu Raty in 2021. The former hurts the most, given how much everyone is clamouring for a top-four right handed defenceman to replace Cody Ceci.
Granted, its always difficult to judge picks made after the fact, as there is no guarantee the Oilers would have picked those players.
This was the trade that appeared to show Ken Holland’s true weakness of overvaluing his former Red Wings, and started the joke that if a player was a former Red Wing then the Oilers would be the ones to trade for him (it didn’t help that literally earlier that day he had made another trade with the Red Wings for Mike Green, which for some reason could not be included in the same deal).
If it is any consolation, the Red Wings didn’t end up with either player either. They traded the Faber pick to the Los Angeles Kings at the draft for a second and a fourth rounder (and L.A. subsequently traded him to Minnesota for Kevin Fiala). They also traded the Raty pick to the New York Islanders for one season of Nick Leddy (who subsequently traded him Vancouver for Bo Horvat).
So in the end, both teams lost?
Best: Dwayne Roloson and Sergei Samsonov, 2006
Unfortunately for Kevin Lowe, the Jim Gregory GM of the Year award wasn’t created until 2009–10, otherwise he would have been an absolute shoo-in for it in 2005–06.
It started with the blockbuster offseason acquisitions of Chris Pronger and Michael Peca, but also continued during the season, where Lowe completed a total of four trades of substance during the year, two of which were at the deadline.
The two prior to the deadline were saw the Oilers acquire not one but two top four defencemen in Jaroslav Spacek and Dick Tarnstrom on January 26, 2006 (it is unclear if Lowe thought that was the deadline day).
The day before the deadline, with everyone in Oil Country clamoring for a goalie to support an otherwise strong team that was being held back by suspect goaltending (sounds familiar…) Lowe acquired Dwayne Roloson from the Minnesota Wild for a first- and third-round pick.
There was some mumbling about whether Roloson was the guy, and if giving up a firs-round pick, to a division rival no less, for a 36-year-old who was the clear backup was a good idea. It wouldn’t help that the Oilers would drop the next three games with Roloson in net, all with save percentages below 0.900.
The day of the deadline saw the Oilers make another big trade. The Oilers traded Marty “a slower Joe Sakic” Reasoner (who actually was fairly productive with 26 points in 58 games), Yan , and a second-round pick for pending UFA Sergei Samsonov. Samsonov would lead the team in scoring with 16 points in his 19 regular season games.
After those initial three losses, the Oilers would go 9–4–4 for the rest of the season, securing a playoff spot in Game 81, with Roloson turning things around in his final 16 games, with a save percentage of 0.916, seventh among all goalies who played at least 10 games during that span, and a GAA of 2.08, good for 4th.
As you may remember, the Oilers would go on to win a few playoff that year, with Roli going supernova and but-for an unfortunate injury in Game 1 of the Stanely Cup Finals was a leading candidate for the Conn Smythe. Samsonov also was a big part of that run, finishing 6th in team scoring with 15 points in 24 games.
So yeah, pretty pretty good.
Worst: Ryan Smyth, 2007
“What goes up must come down.”
That is a perfect description of the difference between the 2005–06 and 2006–07 Oilers seasons, and applies to the trade deadline as well.
After making it to the finals in 2006, the Oilers had a max exodus of crucial players, and were on the outside of the playoffs looking in at the 2007 trade deadline. They were in ninth place in the conference mind you, but they were nine points behind the eighth place Calgary Flames, and so a playoff spot was looking unlikely.
As a result, the Oilers were not going to be buyers at the deadline, and would need to look to the future.
That started 11 days before the deadline, when the Oilers traded defenceman Marc-Andre Bergeron to the New York Islanders, along with a third-round pick, in exchange for 22-year-old former first-round pick Denis Grebeshkov. This wasn’t your typical free agent for a prospect trade mind you, as Bergeron was only 25-years-old and had another two years left on his contract at only $889k per year. But the New York Islanders were gearing up for a playoff run and perhaps Lowe saw that a player with a higher potential than Bergeron was the way to go.
The Oilers did have one very notable upcoming UFA though: Ryan Smyth. Of course, Smyth was the heart and soul of the team, and he and the Oilers were in the midst of negotiating a long term contract for Smyth to continue to stay in the Copper and Blue.
The negotiations stalled, apparently due to a gap of $100,000.00 in annual salary. But the trade deadline time of 3 pm had come and gone, and no trade had been announced, so the Oilers faithful breathed a sigh of relief.
And then we all learned about how there can be a backlog in trade calls.
As it turns out, the Oilers did in fact complete a trade prior to the deadline, sending him to the Islanders (I guess when it’s that last minute you just hit redial on the last GM you made a trade with?).
The Oilers received 21-year-old Robert Nilsson, a first-round pick in 2003, 19-year-old Ryan O’Marra, a first-round pick in 2005, and a first-round pick in 2007. When you look at it in comparison to the Chris Pronger trade the previous summer, where the Oilers received a similar package plus a further first-round pick and second-round pick, it didn’t appear to be the worst value for an upcoming free agent.
But this one probably hurt Oilers fans more, given the attachment to Smyth. Plus, we had all been assured that with the salary cap, losing players over monetary disputes was a thing of the past. Given that Smyth had previously taken some discounts to stay with the Oilers during the budget days, it seemed like even more of a slap in the face.
What makes this trade even worse is that the pieces the Oilers got back ended up being a bust.
The Oilers got one good season out of Nilsson, when he scored 41 points in 71 games as part of the “Kid line” the Oilers had in 200–-08 with Sam Gagner and Andrew Cogliano, but then he never improved on that, playing only a further two seasons before heading to Europe to finish out his career.
Ryan O’Marra only managed to play in 33 NHL games in his career, and the first-round pick was spent on Alex Plante, who got in 10 NHL games.
So yeah, trading the heart of the franchise for essentially nothing in return makes this one of the worst deadline deals for sure.
Best: The 1999 Trade Deadline
The 1999 trade deadline was a wild one for the Oilers that would shape the team for many years, especially if you include the days leading up to it.
On March 20, 1999, three days before the deadline, the Oilers made a massive trade with the Chicago Blackhawks, trading away Boris Mironov and Dean McAmmond (along with Jonas Elofsson) for Daniel Cleary, Chad Kilger, Ethan Moreau, and Christian Laflamme. As was the usual case with the Oilers in the ‘90s, this was a move made due to salary constraints with Mironov in line for a big raise.
Moreau would end up playing 10 more seasons with the Oilers, notching 212 points in 653 games (and a further eight points in 40 games) and eventually end up being named team captain in 2007. Cleary was the next on the list, scoring 86 points in 220 games over the next four seasons.
While Laflamme didn’t do much in his short Oilers tenure, he was a piece the Oilers traded a year later to get Igor Ulanov, so not bad asset management there. Likewise, Kilger wouldn’t do much of anything in three seasons (eight goals and 14 points in 77 games) but would end up being traded for Sergei Zholtok in 2001, who had a hell of run for the Oilers that year.
If this had been the only trade the Oilers made this deadline, then it wouldn’t be on the list, even with Moreau’s longetivity.
But when you combine it with the next two trades, it shows just how much this deadline did for the team’s future.
The next trade was the same day, when the Oilers traded Mats Lindgren and an eighth-round pick for Tommy Salo, who for whatever reason was in Islander’s GM Mike Milbury’s doghouse.
Salo would end up being the Oilers starter for six seasons (including the year of the trade), where the team made the playoffs in four of those years (the last season he was traded at the deadline).
Salo was one of the best goalies in Oilers history. He would end up playing the third most games as a goalie in an Oilers uniform (334), with the third most wins a season with 36 (which was second to Grant Fuhr’s 40 prior to Cam Talbot’s 42), and the third most wins as an Oiler with 147.
He also owns the Oilers career shutouts record with 23, seven more than second place Curtis Joseph, and is tied with Joseph for most in one season with eight. He also has the longest time without a goal against in Oilers history, not letting a goal in for 192:53 in 2000–01, a whopping 25 minutes more than Joseph in 1997–98. He has the lowest GAA of any Oilers goalie at 2.44, 0.28 less than second place Stuart Skinner, and the lowest GAA in a season at 2.22.
So thank you very much Milbury for thinking Felix Potvin was your answer in net.
The final (big) trade of the 1999 deadline was for another future Oilers captain. On the actual deadline of March 23, the Oilers sent a second- and fourth-round pick to the Toronto Maple Leafs for a defenceman named Jason Smith.
“Gator”, as he would later be referred to in the era where hockey nicknames were more than just adding -y or -er to the end of names (same as “Chopper” for the aforementioned Moreau), would end up playing a further seven seasons with the Oilers, five of them as team captain, tying him with Wayne Gretzky for longest tenured in team history (at least until some guy named David O’Connor or something came along).
Smith had a positive plus-minute in all but his last season with the Oilers, and also scored an absolute beauty of a goal in Game 4 against San Jose in 2006 which ended up being the game winner:
So two captains and one of the best goalies in franchise history? Pretty tidy work by Sather.
Also, fun fact: Alexandre Daigle was actually an Oilers for a brief time on January 29, 1999 when he was first traded to the Oilers for Andrei Kovalenko, and then traded later that day to Tampa Bay for Alexander Selivanov.
Worst: Miroslav Satan, 1997
By the trade deadline on March 18, 1997, the Oilers were in fifth place in the Western Conference, well on their way to their first playoff appearance in five years.
A part of that team was a 21-year-old Miroslav Satan, who was sixth on the team in goals with 17 in 64 games, and eighth in points with 28. The previous season, Satan had a similar stat line with 18 goals and 35 points in 62 games. It certainly looked like the Oilers had gotten good value for their fifth-round pick in 1993.
Unfortunately, Satan was up for a new contract, and there was a worry that if the Oilers couldn’t offer what he wanted he would head back to Europe.
So as was the norm for the Oilers in the ‘90s, Satan was traded to the Buffalo Sabres before he got too expensive.
In return, the Oilers received Barrie Moore and Craig Millar. Moore would play a grand total of four games with the Oilers, and then just one more in his NHL career. Millar would play nine times that amount, posting six points in 36 games (although he did score four goals in only 11 games his second season with the team).
Satan, meanwhile, would go on to play another 924 NHL games and score 328 more goals and 672 more points, an average pace of 30 goals and 73 points a season.
Granted, had he stayed, it is likely he would have been gone by the end of his next contract in any event due to finances, and at least Millar was eventually traded for the pick that became Mike Comrie?
Also the Oilers did go on to make the playoffs not only that season but for the next four and five of the next six, so at least it didn’t derail the team.
Best: Doug Weight, 1993
This was another trade done leading up to the deadline, but was within a week so I will count it.
There are actually a lot of trades that could be included as the last “best” one that actually did occur on the deadline: Acquiring Bill Ranford in 1988, Reijo Ruotsalainen in 1990, both playing parts in the 1990 cup run, or players who became mainstays during the ‘90s Copper and Blue era in Todd Marchant in 1994 (and Boris Mironov a week prior) and Janne Niinimaa in 1998.
But I think the acquisition of the last true “Superstar” the Oilers had before Pronger takes the cake.
As the pattern has shown itself here, the Oilers were again faced with trading a key piece of the ‘80s cup teams, this time Esa Tikkanen. As was also the pattern and norm at the time, the Oilers traded him to the New York Rangers, making it the third trade between the two teams that year, and the fourth of five trades that would occur in three season.
In exchange, the Oilers received 21-year-old Doug Weight, who actually had more points than Tikkanen at the time of the trade (40 to 33). The Oilers were actually in New York playing the Rangers on the night of the trade, and both players were actually able to suit up for the new teams right away.
Weight would go on to play eight more seasons for the Oilers, leading the team to those five straight playoff appearances mentioned above. He would pace the Oilers in scoring for seven of those eight seasons (with his 1998–89 season limited to 43 games due to injury), and lead the team in playoff scoring in three of the five post seasons (finishing second in the other two). He further served as the team’s captain for his last two seasons with the club.
While Weight would become a salary casualty himself, he would leave the team sixth in franchise history for points and assists. He was also traded for Reasoner, who was traded at the deadline for Samsonov as discussed above, as well as for Jochen Hecht, who was later traded for the pick that became Jarret Stoll—both of whom helped the team get to the finals in 2006, where they eventually lost to the Carolina Hurricanes who had made a deadline acquisition for…Doug Weight. I don’t know if that really is anything, but like it has to mean something right?
Worst: Jerred Smithson, 2013
This trade is on here, not because it was a bad trade necessarily, but because of the circumstances surrounding it.
Smithson had been a solid fourth line centreman for the past nine years, and a fourth-round pick (who ended up being a player who never played an NHL game) is not a bad price to pay for that kind of depth.
The problem was that it was the only trade the Oilers made on the deadline day (or at least, of substance, to use the term loosely).
This was the first year since 2008 that the Oilers were sniffing a potential playoff spot, and at the time of the deal the Oilers were in 10th place but only a point out of the playoffs. They were also riding a four-game winning streak into the deadline, and it looked like the hope from H.O.P.E. (Taylor Hall, Linus Omark, Magnus Paajarvi, and Jordan Eberle) was finally going to come to fruition. Although Omark wasn’t on the team anymore, and Nail Yakupov was the new guy on the block, so perhaps we should say it was the H.Y.P.E. that was building (please don’t throw things at me).
Suffice it to say, Oilers fans were giddy about the potential return to the playoffs after six seasons, and expectations and excitement was at all an time high for a deadline where the Oilers would finally be a buyer not a seller.
Instead, the only player added was Smithson. Although, to be fair, why mess with a good thing?
The Oilers won their fifth straight game, and second straight against the Flames that night, although Smithson was not in the lineup. That win boosted the team into the eighth and final playoff spot.
The Oilers would then go on to lose their next seven games, and go 3–10 to finish out the season, resulting in a 12th place finish in the conference, a full 10 points out from the playoffs.
Given that finish, one could argue that that it was for the best that the Oilers didn’t go big-fish hunting at the deadline, as otherwise they would have given up a high first-round pick (that the Oilers used to draft Darnell Nurse), and so it would have been even more disastrous. There is also the argument that if things didn’t go as they did during the Decade of Darkness, then the Oilers would not have Leon Draisaitl and Connor McDavid today.
But at the end of the day, when you are battling for a playoff spot, the playoffs are the goal and one would hope the team would take at least a bit of a swing for it, rather than just a bunt. So hopefully Holland doesn’t look at this trade for inspiration this year.
Photo by Curtis Comeau/Icon Sportswire
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