Edmonton Oilers

Six of the best trades in Edmonton Oilers’ history

This past decade, the Edmonton Oilers have had an interesting track record with trades, often finding themselves on the losing side, if not the laughing stock side, of the results. Some of which have found their way onto the worst trades in team history list from earlier this month.

But there is always a flipside. And throughout the team’s lengthy history, there are countless trades that have gone the Oilers’ way and benefitted the team in many ways.

Here are six of the best trades in Oilers history to help us reminisce about some of the most memorable players in Oilers history (and remember times when the team won trades.)

Setting the franchise up early with Semenko and Messier

To Edmonton:

Dave Semenko

1979 third-round pick (Mark Messier)

To Minnesota:

1979 second-round pick (Neal Broten)

1979 third-round pick (Kevin Maxwell)

One of the first trades in Oilers history became one of, if not the greatest, in team history. In August of 1979, the Oilers sent 1979 second- and third-round draft picks to the Minnesota North Stars in exchange for Dave Semenko’s NHL rights (he was already with the Oilers in the WHA, but was drafted by the North Stars of the NHL previously) and a 1979 third. Edmonton’s third-round pick was used to select Mark Messier, one of the best draft picks in team history.

Although the second-round pick that went to Minnesota was used to select Neal Broten, who went on to have an incredible NHL career of his own, this does not even come close to what Messier and Semenko became for the Oilers.

Messier won five Stanley Cups with the Oilers, captaining them to the win once, while recording 1034 points in 851 regular season games and 215 points in 166 playoff games. During his time with the Oilers, he also won a Conn Smythe, Hart Trophy, and Lester B. Pearson Award (now the Ted Lindsay Award.)

Semenko became a beloved member of the team’s dynasty era, taking on the all-too-important enforcer role with the team. He became one of the toughest players to ever step onto the ice. His primary role was more or less as Wayne Gretzky’s bodyguard during his time with the team, helping them along the way to their first two Stanley Cups in 1984 and 1985.

Introducing Weight to the Oilers

To Edmonton:

Doug Weight

To New York Rangers:

Esa Tikkanen

Although it is always challenging to part with a fan favourite, this particular trade was well worth it for the Oilers. Shortly before the trade deadline in the 1992–93 season, Edmonton sent the adored Esa Tikkanen to the New York Rangers in exchange for up-and-coming forward Doug Weight.

At this point in his career, Tikkanen, 28, was passing the peak of his career. The dynamic of the team had changed significantly as nearly the entire identity and core that won all those Stanley Cups had left the organization. The timing ultimately makes sense and the return was fantastic.

Weight was a 22-year-old forward with a ton of offensive upside who was in the middle of his first full NHL season, in which he had 40 points in 63 games at that point. From there, he exploded and lit up the league, even during the Dead Puck Era.

He was nearly a point-per-game player in his nine seasons with the Oilers, scoring 577 points in 588 games. Weight even managed to hit 100 points once, finishing with 104 in the 1995–96 season. Making this even more impressive is that only three players on the team that season even hit 40 points, showing just how much of a force he was with Edmonton.

Weight also spent his final two and a half seasons with the Oilers as team captain. He was one of the most talented players to come through Edmonton in the post-dynasty years.

The legend of Niinimaa was born

To Edmonton:

Janne Niinimaa

To Philadelphia:

Dan McGillis

1998 second-round (Jason Beckett)

It is always difficult to find top-pairing defenders who can literally do it all. This trade between the Oilers and Philadelphia Flyers near the 1998 trade deadline brought in one of the most recognizable and important defenders Edmonton has had in the past 25 years.

In exchange for Dan McGillis and a second-round draft pick at the 1998 draft, Edmonton acquired Janne Niinimaa.

The Finnish defender was off to a hot start with the Flyers, where he already had 78 points in 143 games.

Although his next couple of seasons did not quite live up to the offensive potential seen in his past seasons, scoring 28 and 33 points respectively, Niinimaa became a stalwart on the Oilers’ top pairing. He was a workhorse, averaging over 25 minutes of ice time per game with Edmonton, hitting a peak of 26:48 per game in 63 games during his last season with the Oilers.

Niinimaa took on all of the toughest matchups and quarterbacked the top powerplay unit (despite a wild and unpredictable shot that kept everyone on their toes.) He became the most important defender on the roster and found his way to the All-Star Game in 2001. Although he was only in Edmonton for parts of six seasons, he made a huge impact on the team and the city.

Trading for yet another future captain

To Edmonton:

Jason Smith

To Toronto:

1999 fourth-round pick (Jonathan Zion)

2000 second-round pick (Kris Vernarsky)

At the time of this trade, Jason Smith was a former first-round pick who was just establishing himself as a solid, reliable, and physical defensive defender in the league. One would think it would take more than a second and fourth round draft pick to acquire him, right?

But nevertheless, the Oilers pulled this one off and got Smith, who turned out to be an absolute warrior for the franchise.

Right from the get-go, Smith took on a huge role as the main shut-down member of the defence. He averaged just over 21 minutes of ice time per game during his time in Edmonton, indicating his role on the team. He also possessed plenty of leadership qualities, and became team captain after two seasons with the team.

He spent five seasons in that role, at the time tying Wayne Gretzky for longest tenured captain of the franchise, and led the team to the unexpected Cup run in the 2005–06 season.

Smith was a steal for the Oilers, especially considering the picks they gave up never really panned out into anything.

Introducing the Pronger saga

To Edmonton:

Chris Pronger

To St. Louis:

Eric Brewer

Doug Lynch

Jeff Woywitka

This is one of, if not the, biggest trade in franchise history, in terms what was being acquired. Chris Pronger, at the time, was one of the top defenders in the entire league. He was four seasons removed from winning the Hart and Norris Trophies, could regularly hit 50 points in a season, and had averaged over 29 minutes of ice time per game in the past nine seasons leading up to this trade.

Pronger was an absolute gamechanger for the Oilers franchise and he was one of the biggest reasons why they were able to go on a miraculous run to the Stanley Cup Finals during his one season in Edmonton, 2005–06.

And they acquired him for a fairly cheap price as well, as Eric Brewer was the only regular NHLer that was included in the return package.

In his one season as an Oiler, Pronger scored 56 points in 80 games averaging 27:59 in ice time per game during the regular season. He stepped it up even more in the playoffs with 21 points in 24 games while playing over 30 minutes per game. Fun piece of trivia as well, he became the first player to score on a penalty shot in Stanley Cup Finals history during that run.

Pronger’s absolutely dominant style of play gave the Oilers the type of player they had sorely missed for years. It is a shame the tenure with the team ended as bitterly and quickly as it did, as it would have been incredible to get to watch Pronger in his prime for a couple more seasons in Edmonton.

Klefbom: What could have been

To Edmonton:

Colten Teubert

2011 first-round pick (Oscar Klefbom)

2012 third-round pick (Daniil Zharkov)

To Los Angeles:

Dustin Penner

The entire debacle of Dustin Penner’s acquisition and tenure with the Edmonton Oilers is a story in and of itself, but at the very least the Oilers were able to pull this trade off on his way out.

After four seasons with the team, one of which included a career high 32 goals and 63 points, Penner had worn out his welcome with the Oilers front office staff. They shipped him off to the Los Angeles Kings in exchange for defender Colten Teubert, a 2011 first-round pick, and a 2012 third-round pick.

Teubert and the player selected with the third, Daniil Zharkov, did not pan out. But the player they got with the first rounder, Oscar Klefbom, was well worth this trade.

Klefbom took a few seasons to develop but when he joined the Oilers on a more permanent basis for the 2014–15 season, he quickly became a fan favourite and frequently relied on by the coaching staff. He was a calm and collected defender who was proficient at both ends of the rink and could handle nearly any situation with ease.

He was well on his way to becoming a top defender in the league, averaging over 22 minutes per game during his time with the Oilers. Unfortunately, just as he was beginning to truly shine alongside fellow Swede, Adam Larsson, on the Oilers’ top pairing, lingering shoulder issues flared up after a couple of devastating hits.

After a few attempted comebacks, he was never quite able to stay regularly in the lineup long-term as his shoulder was still an issue for him. Although Klefbom has never officially retired, it is generally accepted that his playing career is over as he has not played since 2019–20 and he is now focusing on quality of life while managing and rehabbing his shoulder.

For Oilers fans, Klefbom is a major case of “what could have been?” And there isn’t a fan in Oil Country anywhere that does not miss him.

Those are six of the best trades in Oilers history. The ones included on this list feature many players who became big name members of the Oilers organization, plenty of team captains and integral contributors to team success. Which ones would you add to this list? Drop a comment down below!

Photo by Brett Holmes/Icon Sportswire

Sean Laycock

Sean is a stubborn, lifelong Oilers fan who lives by the motto "There is always next year".


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