6 massive rumoured Edmonton Oilers trades that almost happened
There have been more than a few “What if?” moments in Edmonton Oilers history.
Lately, it seems like the entire fanbase has been captivated by the simple two-word questions, particularly when it comes to the team’s two failed Stanley Cup Final runs in 2024 and 2025.
What if the Oilers managed to win the Stanley Cup in one of those years? Would it have led to Connor McDavid signing a long-term extension? What would the celebration have been like?
Those are painful questions for an NHL fanbase yearning to taste glory once again, but it’s far from the only instance of “What if?” in Oilers history. In fact, the team has a long and storied history of those types of moments, particularly when it comes to uncompleted trades.
On more than one occasion, the Oilers have been rumoured to be part of a trade that would have shaken the entire league, but for whatever reason, never materialized.
What did those major, uncompleted trades look like? Here are the six biggest ones that leave fans thinking, “What if?”
1. Superstar swap with Tampa Bay
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Rumoured trade:
Edmonton Oilers acquire: Nikita Kucherov and Anthony CirelliĀ
Tampa Bay Lightning acquire: Leon Draisaitl
Following the 2018-19 season, there was a lot of angst in both Edmonton and Tampa Bay.
The Oilers missed the playoffs for the second-straight season, and the Lightning were coming off an embarrassing four-game sweep at the hands of the Columbus Blue Jackets. The desire for change was strong in both markets, and it nearly led to an earth-shattering trade between the teams.
According to NHL insider Jeff Marek on a 2024 episode of The Sheet, the Oilers and Lightning were deep in talks around a Leon Draisaitl/Nikita Kucherov swap. The snag that killed the deal was Edmonton wanting Tampa Bay to include Anthony Cirelli.
2. The other “one-for-one” Taylor Hall trade
Rumoured trade:
Edmonton Oilers acquire: Cody Ceci
Ottawa Senators acquire: Taylor Hall
Many Oilers fans still know where they were when Taylor Hall was traded to the New Jersey Devils, one-for-one, for Adam Larsson back in the summer of 2016.
Edmonton was desperate to improve their defence, and then-GM Peter Chiarelli seemed eager to use Hall in order to achieve that. That deal is looked back on as being an infamous moment in franchise history, but it was almost so much worse.
According to TSN’s Darren Dreger, speaking on the now-defunct TSN 1260 in Edmonton back in 2018, the Oilers almost shipped Hall to the Ottawa Senators for a young Cody Ceci. The issue that prevented the trade is that Ottawa couldn’t clear the move with ownership before Hall was sent to New Jersey instead.
3. Dany Heatley vetoes Oilers
Rumoured trade:
Edmonton Oilers acquire: Dany Heatley
Ottawa Senators acquire: Andrew Cogliano, Dustin Penner, and Ladislav Smid
Back in the summer of 2009, Edmonton was desperately trying to make a big splash and return to playoff contention. To do so, then-GM Steve Tambilini was hot on the heels of Ottawa superstar Dany Heatley, who was fresh off a 39-goal campaign and was being shopped by the Senators.
The Oilers actually got the Senators to agree to a trade package that included Andrew Cogliano, Dustin Penner, and Ladislav Smid, but the entire thing was vetoed by Dany Heatley, who refused to waive his trade protection to go to Edmonton.
4. A king’s ransom for PK Subban
Rumoured trade:
Edmonton Oilers acquire: PK Subban
Montreal Canadiens acquire:Ā Leon Draisaitl, Oscar Klefbom/Darnell Nurse, 2016 4th-overall pick, and another unknown asset
The Oilers’ pursuit to improve their defence in the summer of 2026 led them in a lot of wild directions.
It was Taylor Hall who would eventually be traded to New Jersey, but Chiarelli was also chasing down Montreal Canadiens star PK Subban at the draft. The Canadiens were interested in making a deal with the Oilers for Subban, but they maintained a sky-high asking price to make it happen.
NHL insider Elliotte Friedman reported that the trade on the table involved Leon Draisaitl, one of Oscar Klefbom or Darnell Nurse, the Oilers’ 2016 4th-overall pick, and an additional unknown asset. That was an astounding price for the Oilers to pay at the time, and Chiarelli wisely refused.
5. Pronger jumps to Toronto
Rumoured trade:
Edmonton Oilers acquire: Tomas Kaberle, Matt Stajan, 2007 first-round pick, and 2008 first-round pickĀ
Toronto Maple Leafs acquire: Chris Pronger
When Chris Pronger demanded out of Edmonton after the 2006 Stanley Cup run, the Oilers had options.
The Anaheim Ducks eventually swung the deal to land Pronger, but another team deep in talks with the Oilers were the Toronto Maple Leafs. In a 2020 Spittin’ Chiclets episode, Pronger revealed that the Leafs were willing to give up Tomas Kaberle, Matt Stajan, and two first-round picks to acquire him.
Then-Oilers GM Kevin Lowe demanded that the Leafs include Alex Steen, which led to trade talks breaking down.
6. Gretzky to the Red Wings?
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Rumoured trade:
Edmonton Oilers acquire: unknown
Detroit Red Wings acquire: Wayne Gretzky
We all know the story behind the Oilers trading Wayne Gretzky to the LA Kings, but did you know that it was supposed to be the Detroit Red Wings?
According to the Great One himself on a Spittin’ Chiclets podcast in 2022, when it became apparent that a trade was imminent, the Oilers allowed Gretzky to choose his preferred destinations among the interested teams. The Kings and Red Wings emerged as the favourites, and Gretzky initially chose the Red Wings.
He grew up a Red Wings fan and idolized Gordie Howe, so it made sense. Yet, it was his dad, Walter Gretzky, who convinced him to forge his own path and go to L.A. instead.