- The Edmonton Oilers were part of the biggest trade in the history of the NHL.
- Edmonton’s trade for Chris Pronger inspired an unlikely run to the Stanley Cup Final.
- Doug Weight and Ryan Smyth were also part of important trades.
A big trade can change a team’s identity, impact their Stanley Cup odds, and reinvigorate (or piss off) a fanbase.
And perhaps no team in the NHL knows this better than the Edmonton Oilers, the team that traded Wayne Gretzky when he was at the height of his powers.
That infamous trade tops my list of the seven biggest trades in Oilers’ history.
1. Wayne Gretzky, Marty McSorley, Mike Krushelynski for Jimmy Carson, Martin Gelinas, Three First-Round picks, and $15 Million
When you mention “The Trade” in hockey circles, everyone knows what you’re talking about.
No deal has had a bigger impact on the league – and the sport – than the trade that saw Gretzky move from Edmonton to the Los Angeles Kings in 1988.
Gretzky won four Stanley Cups and established himself as an all-time great in Edmonton, but financial stresses caused ownership to deal “The Great One” rather than run the risk of him leaving for nothing in free agency.
Gretzky’s move to Los Angeles not only ended the Oilers’ dynasty but it also played a monumental role in growing the sport in California and the rest of the United States.
2. Mark Messier for Louie DeBrusk, Bernie Nicholls, and Steven Rice
As if trading Gretzky wasn’t tough enough for the Oilers, a few years later, they dealt away his dynasty running mate Mark Messier to the New York Rangers.
Messier, named captain after Gretzky’s departure, led the Oilers to five Stanley Cups and recorded 1,034 points in 851 games in Edmonton.
He would lead the Blueshirts to the 1994 Stanley Cup, ending a 54-year drought.
3. Eric Brewer, Doug Lynch, and Jeff Woywitka for Chris Pronger
Chris Pronger’s tenure in Edmonton lasted just one season, but the hulking defenceman left a lasting impact.
Pronger was a beast on the blue line during the regular season, but he took things to a new level in the playoffs for the Oilers, who weren’t expected to be contenders according to their hockey odds to win the Stanley Cup.
Pronger notched 21 points in 24 games and led the eighth-seeded Oilers on a memorable run to Game 7 of the Stanley Cup Final.
4. Esa Tikkanen for Doug Weight
This deal with the Rangers worked out for both teams.
Esa Tikkanen would play for the Rangers in their championship run, while Weight put together a terrific career with the Oilers.
Weight spent nine seasons in Edmonton and served as the team’s captain from 1999-2001. Weight’s 577 points are 10th in franchise history.
5. Ryan Smyth for Robert Nilsson, Ryan O’Marra, and a First-Round Pick
The on-ice impact of this deal is not profound.
Ryan Smyth spent a couple of months on Long Island with the Islanders, while none of Robert Nilsson, Ryan O’Marra, or Alex Plante (who they selected with the first-round pick) amounted to much for the Oilers.
Off the ice, however, this was a massive deal.
Smyth was the heart and soul of the Oilers and seeing him get moved was a reminder that anybody can be traded in this business. It was such an emotional situation that Smyth broke down in tears during a press conference before departing for Long Island.
6. Tyson Barrie, Reid Schaefer, a First-Round Pick, and Fourth-Round Pick for Mattias Ekholm
For a long time the Oilers were searching for a No. 1 defenceman to provide some defensive support for Connor McDavid and Leon Draisaitl.
That hunt came to an end at the 2023 trade deadline when the Oilers acquired Mattias Ekholm from the Predators for a package that included Tyson Barrie.
Ekholm has been a rock on the blue line since the deal and he played a massive role in the Oilers reaching the 2024 Stanley Cup Final.
7. Chris Pronger for Joffrey Lupul, Ladislav Smid, Two First-Round Picks, and a Third-Round Pick
Pronger’s time in Edmonton was electric, but it came to an ugly end when he asked for a trade for family reasons.
The deal worked out wonderfully for Pronger and the Anaheim Ducks, winners of the 2007 Stanley Cup, but the Edmonton side of the trade was a mixed bag.
One of the draft picks was used to select Jordan Eberle and Ladislav Smid was a contributing player for a number of years, but that pales in comparison to what Pronger brought to Anaheim.