Worst Trades in Oilers History

Trades provide each and every NHL team with the opportunity to immediately address glaring needs within their respective rosters. Good trades can set your franchise up for incredible success. Bad trades can leave you without a GM and needing to hire a new manager and coach in the offseason.

The Edmonton Oilers are not the only team to make poor trades. That said, they’ve had their fair share of whoppers.

Since their entrance into the NHL in 1979, the Oilers’ success throughout their history has been highly dependent on the outcome of the trades. Some were good (Wayne Gretzky was rumored to have been won in a board game) and others have gone horribly wrong (fans are finally starting to get over the Taylor Hall deal).

Substack The Hockey Writers Edmonton Oilers Banner

When the Oilers replaced GM Peter Chiarelli with veteran Ken Holland, they removed a conductor who was known for orchestrating bad trades. As Chiarelli’s reputation followed him out the door, Holland was tasked with reshaping a squad that included players from some of the worst trades in Oilers’ history. Essentially keeping only a handful of key pieces from the Chiarelli era, Holland started with Connor McDavid, Leon Draisaitl, Ryan Nugent-Hopkins, and went to work. Not every trade has been a steal. That said, his deals to land Mattias Ekholm, and last season’s trade to pluck Klim Kostin from the St. Louis Blues were both considered huge wins.

Today, the Oilers are in much better shape but trade blunders are still very much a part of why some fans suggest the Oilers have failed players like McDavid and Draisaitl. Here are a number of the worst trades in Oilers’ history.

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, 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 not yet developed into a quality NHL defender. Years later, he’s now officially no longer seen as a viable prospect and not in the NHL.

In his first season with the Oilers, Reinhart struggled to stay in the lineup and was eventually demoted to the American Hockey League. He couldn’t think the game quickly enough, his speed was a factor and despite great numbers for the Edmonton Oil Kings before going to the New York Islanders, he was never able to make it work in the NHL.

He became a prospect of the Vegas Golden Knights but fizzled out there as well.

The kicker was what Edmonton wound up giving away in the deal. While insiders and those near the Oilers franchise have publicly stated they weren’t going to take him, Mathew Barzal was available at one of the spots the Oilers gave away to acquire Reinhart. Barzal has become a dynamic center in the NHL. The Winnipeg Jets also drafted Kyle Connor at No. 17. He’s arguably the best scorer on their team and would have been an incredible fit with McDavid and Draisaitl on the Oilers team this season.

Brock Boeser was taken by the Canucks at N2. 23 and he’s burning their Oilers in their 2023-24 playoff series.

Oilers Trade Future Hall-of-Famer

Oilers Acquire: Craig Simpson, Dave Hannan, Chris Joseph and Moe Mantha

Penguins 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.

Defenseman Paul Coffey of the Edmonton Oilers
Paul Coffey, Edmonton Oilers (Photo by Bruce Bennett Studios/Getty Images)

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.

Paul Coffey came back to the organization as a skating and skills coach and is now an assistant coach working with Kris Knoblauch.

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 that 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 his first year with Edmonton, the Oilers determined he had no future within their organization. He went on to record back-to-back 20-goal seasons 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.

This was a trade that looked good for about a year and as time has gone by isn’t as painful as some others. Pitkanen did play well for the Oilers in one season and Lupul is out of the NHL. That said, Lupul was the best player in the deal.

Culture Change My A–

Oilers Acquire: Adam Larsson

Devils Acquire: Taylor Hall

One of the biggest blunders Chiarelli made while running the Oilers was in convincing himself that Taylor Hall was a problem in the dressing room and that this problem was reason enough to move a future league MVP for a second-pairing, (on a good night first-pairing) defender.

Hall did have a bit of an attitude but he was one of the Oilers’ best forwards. He made a fair salary and he was still young. The deal was one-for-one for Adam Larsson with the New Jersey Devils and Oil Country was bonkers almost immediately.

Related: Taylor Hall for Adam Larsson Trade Revisited

Almost as troubling, the Oilers went and spent the $6 million per season they were giving Hall on Milan Lucic. Lucic had one good season before his game completely fell off the rails. The Oilers got lucky they were able to ship Lucic to the Calgary Flames for James Neal who scored 19 goals in a shortened season. Even James Neal failed to work out and was bought out by Edmonton.

In retrospect, Larsson turned out to be a good player for the Oilers, but he left for Seattle in free agency and the Oilers got nothing in return. They signed Cody Ceci to fill his spot and he’s been up and down as a polarizing player for many fans.

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 agree on a contract that 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.

Ryan Smyth
Ryan Smyth, Edmonton Oilers, Mar. 2, 2004 (Photo by Elsa/Getty Images)

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 that the Oilers received was nowhere near substantial providing they had moved one of their most skilled and respected players. Smyth did eventually return to Edmonton, but he was on the backside of his career.

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 campaigns 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 Final 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 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 that 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.

Salary Cap Relief

Oilers Acquire: Ryan Strome

New York Islanders Acquire: Jordan Eberle

Another whopper of a trade from Chiarelli, the Oilers felt like they needed to drop some salary so after one bad playoff series, they moved Jordan Eberle to the New York Islanders.

Eberle was a consistent 20-goal scorer and Strome hadn’t done much beyond one decent season. This was a top-six forward for a depth player and it didn’t go well. Strome came to Edmonton and did next to nothing. He was eventually moved to the New York Rangers where his replacement, Ryan Spooner did even less. Of course, Strome flourished in a different environment. He posted multiple 50-plus point seasons for the Rangers.

There have been so many trades since that tracing back the trade becomes like playing a game of Six Degrees of Kevin Bacon. What’s important to remember is that Eberle scored close to or more than 20 goals each season after he left Edmonton and stayed exactly the type of scorer the Oilers would have loved to have had since his departure. There was even talk at this past deadline that Edmonton inquired with Seattle about a deadline deal to bring Eberle back.

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 was 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 McSorley, 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 McSorley 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.

Wayne Gretzky, Los Angeles Kings
Wayne Gretzky, Los Angeles Kings, Dec. 4, 1994 (Photo By Andrew D. Bernstein/Getty Images)

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.

You may also like:

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!