Trades, and the NHL Deadline in particular, provide each and every NHL team with the opportunity to immediately address glaring needs within their respective rosters. Completing a major trade can influence great change within a select organization, molding a team into an instant contender rather than an annual pretender.
However, major trades in the NHL, especially in the Salary Cap era, come with their fair share of risk. If a trade fails to pan out for a given team involved, the repercussions can detriment a club for considerable years into their future, leading them to regret agreeing to said trade in the first place.
For the Edmonton Oilers, this could not ring more true.
Since their entrance into the NHL in 1979, the Oilers have made their fair share of trades, some have worked out for the better, while others have not. And while the Oilers’ success throughout their history is highly dependent on the outcome of the trades which they have made, those which have gone wrong, and there have been plenty, always seem to outweigh the positive.
With that being said, here are a number of the worst trades in Oilers history. The following list is in no particular order, however, I have a feeling that we can all anticipate which hurt the Oilers the most.
Draft Day Blunder
Oilers Acquire: Griffin Reinhart
Islanders Acquire: Edmonton’s 2015 16th and 33rd Overall Draft Picks
On the first day of the 2015 NHL Entry Draft, Peter Chiarelli made his first big splash as the new General Manager of the Edmonton Oilers, trading two draft picks in exchange for prospect defenseman Griffin Reinhart.
Reinhart, who himself was selected fourth overall in the 2012 Draft, had, and has yet to develop into a quality NHL defender, as Chiarelli had thought he would. In his first season with the Oilers, Reinhart struggled to stay in the lineup and was eventually demoted to the American Hockey League, where his play has been under-whelming.
For the Islanders, they used the 16th overall selection to acquire a highly talented forward in Mathew Barzal, who played with Team Canada at the 2016 World Junior Championship. The Islanders then went on to package the 33rd overall selection to Tampa Bay in return for an additional first round pick. Barzal, a center, has played his junior hockey with the Seattle Thunderbirds, and has produced offensively at nearly a 2.00 points per game pace in 2015-16.
Oilers Trade Future Hall of Famer
Oilers Acquire: Craig Simpson, Dave Hannan, Chris Joseph and Moe Mantha
Islanders Acquire: Paul Coffey, Dave Hunter and Wayne Van Dorp
In November of 1987, the Oilers found themselves within a financial dispute with star defenseman Paul Coffey, who had recently helped lead the Oilers to their third Stanley Cup Championship. As a result, Coffey was traded to the Pittsburgh Penguins, where he not only helped lead them to a Stanley Cup in 1991, but also produced two seasons of greater than 100 points scored.
On the other hand, the Oilers’ major addition was Craig Simpson, who notched three seasons of 30 goals, including a 43 goal campaign in his first year with the team. However, the presence of Hannan and Mantha lasted a mere season, while Joseph’s time within the organization was spent evenly between the NHL and AHL. Simply put, the Oilers’ return was not a substantial enough return for a future Hall of Fame defenseman.
Patience is Key
Oilers Acquire: Joni Pitkanen, Geoff Sanderson and a third round pick
Flyers Acquire: Joffrey Lupul and Jason Smith
Acquired by the Oilers in the trade which sent Chris Pronger to the Anaheim Mighty Ducks, Joffrey Lupul was projected to be a major offensive contributor with the Oilers in coming years, yet after failing to live up to a 28 goal sophomore season in first year with Edmonton, the Oilers determined he had no future within their organization. He went on to record back to back 20 goal season with the Flyers. Heading to Philadelphia with Lupul was the Oilers’ Team Captain, Jason Smith.
In return, the Oilers received Joni Pitkanen and Geoff Sanderson. Pitkanen, who had scored 43 points the previous season with the Flyers, managed just 26 in his only season with the Oilers, and exactly one-year after he arrived, the Oilers traded him to the Carolina Hurricanes. Just 26 years of age at the time, Pitkanen had yet to truly reach his potential, as was witnessed by his return to the 46 point season total a mere two seasons later. Sanderson too also played a single season with the Oilers, as he retired following the 2007-08 campaign.
A Tearful Goodbye
Oilers Acquire: Ryan O’Marra, Robert Nilsson and a first round pick (Alex Plante)
Islanders Acquire: Ryan Smyth
As the 2007 NHL Trade Deadline approached, the Oilers and Ryan Smyth had failed to come to an agreement on a contract which would extend Smyth’s time in Edmonton. Having spent the first 12 years of his career with the Oilers, Smyth was understandably upset when he was traded by his much beloved team to the New York Islanders, who were preparing for a playoff push.
In return for the highly sought after commodity, the Oilers received Ryan O’Marra, Robert Nilsson and Alex Plante. While Nilsson played three roughly successful seasons for the Oilers, O’Marra managed just 31 total games, in which he scored one goal and seven points, not a great return from two former first round picks. Lastly, Alex Plante, the defenseman selected by the Oilers 15th overall in 2007, managed to play just 10 games with Edmonton, scoring two points.
Although Smyth would only play 18 games for the Islanders before moving on to Colorado, the return which the Oilers received was nowhere near substantial providing they had moved one of their most skilled and respected players.
A Nightmarish Trade
Oilers Acquire: Craig Millar and Barrie Moore
Sabres Acquire: Miroslav Satan
In 1993, the Oilers drafted Miroslav Satan in the fifth round, 111th overall. Less than four years later, he, like so many others who have donned an Edmonton jersey over the years, was traded before he was able to develop into a quality NHL player. Sent to the Sabres, Satan, who was only 22 years old at the time, would go on to become one of the greatest players in Buffalo history, leading his team in scoring in six of eight seasons while recording two 30 goal and one 40 goal campaign in the process.
For the Oilers, they had once again traded away a future talent for a poor return. Barrie Moore would play just four games with the Oilers, while Craig Millar played in a mere 36, recording six points in the process.
The trade paid huge dividends for the Sabres, who, led by Satan (no pun intended), would reach the Stanley Cup Finals in 1999.
Everyone Must Go!
Oilers Acquire: Shayne Corson, Brent Gilchrist and Vladamir Vutjek
Canadiens Acquire: Vincent Damphousse and a fourth round pick (Adam Wiesel)
In the Summer of 1992, the Oilers once again felt the need to trade one of their top offensive players.
An incredibly consistent performer, Vincent Damphousse had been acquired from the Toronto Maple Leafs before the 1991-92 season in a trade which involved Oiler greats Glenn Anderson and Grant Fuhr. However, Damphousse would only play one season in an Oilers uniform, despite scoring 38 goals and leading the team in points with 89 points.
The following Summer, the Oilers would trade Damphousse to Montreal in exchange for Shayne Corson, Brent Gilchrist and Vladamir Vutjek. While Damphousse would go on to score 498 points over 519 games with the Canadiens, as well as win a Stanley Cup in his first year with the team, Edmonton was far less fortunate with their return. Although Corson would play three successful seasons with the Oilers, where he was named, and then stripped of the Captaincy, he too would be traded come 1996.
On the other hand, neither Gilchrist or Vutjek would find considerable success with the Oilers. Gilchrist played one season, recording 10 goals and 20 points, while Vutjek played parts of two seasons in Edmonton, totaling 30 points in 70 games played.
Moose in the Big City
Oilers Acquire: Bernie Nicholls, Louie DeBrusk, Steven Rice, David Shaw
Rangers Acquire: Mark Messier, Jeff Beukeboom
After helping lead the Oilers to five Stanley Cup Championships alongside 1034 points in 851 games played, Mark Messier requested a trade out of Edmonton, upset that the team had let an up and coming Adam Graves test Free Agency and sign with the New York Rangers.
So, the Oilers re-united the pair, sending Messier to the Rangers in return for a handful of players, most notably Bernie Nicholls, who would go on to play in just 95 games with the Oilers before he too was traded. In DeBrusk, the Oilers received a grinder who played five seasons with the club, yet was best known for his ability to protect his teammates. Further, Rice, who spent two seasons with the Oilers, compiled 39 points over 91 games, while Shaw played in just 12 games with the club. Both were traded by Edmonton within two years time.
Meanwhile, Messier went on score 691 points in 698 games with the Rangers, while also leading them to a Stanley Cup Championship in 1994. He was inducted to the Hockey Hall of Fame in 2007.
The Expendable One
Oilers Acquire: Jimmy Carson, Martin Gelinas, three first round picks (Corey Foster, Martin Rucinsky, Nick Stajduhar) and $15 Million.
Kings Acquire: Wayne Gretzky, Mike Krushelnyski and Marty McSorley
August 9, 1988.
This day has never been forgotten by Oilers faithful, as it way the day in which they watched the best player in NHL history leave town in a trade with the Los Angeles Kings. Peter Pocklington, the Oilers’ owner at the time, had been experiencing well documented financial problems, an issue which generated the initial idea of trading Gretzky.
In the deal, the Kings not only received the best player in the game, but also his intimidating line-mate in Marty McSorely, one of the game’s premier enforcers who could also do damage offensively. Further, they landed Mike Krushelnyski, an offensive forward who had scored 43 goals with the Oilers four years prior. Gretzky and McSorely helped lead the Kings to the Stanley Cup Final in 1993, while Gretzky quite obviously went on to set a number of insurmountable NHL records.
The Oilers, quite clearly known for their inability to land a solid return in major trades, landed a skilled player in Jimmy Carson, yet after one season and 100 points later, the Oilers decided to trade him too. He wound up in Detroit while Adam Graves returned to the team, having essentially cost them both Messier and Carson. In Martin Gelinas, the Oilers received four seasons of mediocre production before they decided to trade the then 22 year-old to the Quebec Nordiques. Yet to truly develop, Gelinas carved out a highly successful career in the NHL outside of Edmonton.
Lastly, let’s not forget the three first round picks received by the Oilers in the deal. The first of which, the Kings’ 1989 first round pick, was traded by the Oilers to New Jersey for Corey Foster, who never played a game for the Oilers. In 1991, the Oilers used their second pick from the Kings to draft Martin Rucinsky 20th overall, yet after he failed to become a superstar two games into his career with Edmonton, he was traded (surprisingly) to the Nordiques. He went on to play nearly 1000 NHL games and record over 600 career points. Finally, the Oilers used their final pick from the Kings to select Nick Stajduhar 16th overall in 1993. He played two games with the Oilers scoring no points.
The $15 Million was an important feature, yet in no way would it ever replace the potential Stanley Cup Championships which could have been had the Oilers held onto Gretzky.
What Oilers trade do you feel is the worst of all-time? Feel free to comment below!