There are “what if?” moments, and then there are the kinds that can alter the entire shape of a franchise.
The Edmonton Oilers have plenty of both, but some of the biggest ones never even made it to the finish line. Over the years, the team has been tied to a handful of blockbuster trades that were discussed, negotiated, and in some cases nearly done - only to collapse before the league ever got to react.
The most jaw-dropping one may be the Leon Draisaitl idea that surfaced after the 2018-19 season. According to NHL insider Jeff Marek on a 2024 episode of The Sheet, Edmonton and Tampa Bay were deep in talks on a Draisaitl-for-Nikita Kucherov swap.
The sticking point was Anthony Cirelli, with the Oilers wanting him included in the deal. Tampa Bay had just been swept by the Columbus Blue Jackets, Edmonton had missed the playoffs for a second straight year, and both sides were clearly looking for a shakeup.
Another near-miss came in the summer of 2016, when Taylor Hall was eventually dealt to New Jersey for Adam Larsson. That trade already sits in Oilers lore, but it could have gone in a different and arguably worse direction.
TSN’s Darren Dreger said on the now-defunct TSN 1260 in Edmonton in 2018 that Edmonton nearly sent Hall to the Ottawa Senators for Cody Ceci. Ottawa never got ownership approval in time, and Hall ended up headed to the Devils instead.
The Oilers were also in the middle of the Dany Heatley sweepstakes in 2009. Edmonton was trying to push back into playoff contention, and then-GM Steve Tambellini was chasing the Ottawa winger after his 39-goal season. Ottawa had reportedly agreed to a package built around Andrew Cogliano, Dustin Penner, and Ladislav Smid, but Heatley shut it down by refusing to waive his trade protection to come to Edmonton.
Defence was the obsession in those years, and PK Subban was another name that came up in a huge way. At the 2016 draft, Peter Chiarelli was pursuing the Montreal Canadiens star, but the price was enormous.
Elliotte Friedman reported that Montreal’s ask involved Leon Draisaitl, one of Oscar Klefbom or Darnell Nurse, the Oilers’ 2016 fourth-overall pick, and another unknown asset. Edmonton passed, and given the haul, it was hardly a surprise.
Chris Pronger’s exit from Edmonton after the 2006 Stanley Cup run opened the door to another almost-trade, this time with Toronto. Pronger said on a 2020 Spittin’ Chiclets episode that the Maple Leafs were prepared to send Tomas Kaberle, Matt Stajan, and two first-round picks.
Kevin Lowe wanted Alex Steen added to the package, and once that demand went unmet, the talks fell apart. Pronger eventually landed with the Anaheim Ducks.
And then there’s the biggest “what if” of all: Wayne Gretzky. Most fans know the Oilers sent him to the Kings, but Gretzky said on a 2022 Spittin’ Chiclets podcast that Detroit was originally one of the leading options.
When the trade became unavoidable, Edmonton let him pick from the interested teams. Gretzky initially chose the Red Wings, where he had grown up a fan and idolized Gordie Howe.
In the end, Walter Gretzky talked him into going to Los Angeles instead.
In Other News...
Oilers Win Now Wishlist Is Starting To Come Into Focus
The Oilers long-term shopping list is already starting to take shape, and it is built around the same kind of win-now logic that has defined so much of the conversation in Edmonton. With a 2027 free-agency window in mind, the idea is less about fantasy names and more about identifying players who could actually be available, fit the roster and push the team closer to another playoff run. That makes the exercise feel practical even if it is still firmly in the speculative stage.
Jason Robertson, Alex Debrincat, Vince Dunn and Jordan Binnington all surface as the sort of targets that could move the needle if the right circumstances line up. Robertson would require a lot of cap maneuvering, Debrincat carries the appeal of a long-standing fit, Dunn would answer a need on the back end and Binnington would only enter the picture if Edmonton keeps searching for stability in goal. None of it is imminent, but the list says plenty about where the Oilers are already trying to position themselves. [Read more 🡒]
Ducks Landed On The Wrong End Of An Oilers Night Fans Wont Forget
The Oilers 2025-26 season had its share of uneven stretches, but January gave them a run of nights that stood out even in a year that ended with a first-round playoff exit. Connor Clattenburgs NHL debut added a fresh prospect storyline to the mix, while an eight-game homestand turned into one of the most memorable offensive bursts of the season, highlighted by back-to-back hat tricks from defensemen Evan Bouchard and Mattias Ekholm.
Bouchards big night came in a wild overtime win, and Ekholm followed two days later with a three-goal performance against Anaheim that capped the kind of blue-line scoring binge few teams ever see. Edmonton also finally strung together its first three-game winning streak late in the year, a small but notable sign of momentum during a season that kept swinging between frustration and flashes of something more promising. [Read more 🡒]
Patrick Kane's Return Says Everything About Where Blackhawks Believe They're Headed
The Oilers are being linked to another aggressive swing as they weigh a possible move for Steven Stamkos, a rumor that fits the same win-now posture that has defined so much of their thinking around Connor McDavid and Leon Draisaitl. Edmonton has already shown a willingness to chase proven help when the window feels open, and any conversation about adding a player of Stamkos stature only reinforces how little patience this front office appears to have for a slow build.
What makes the chatter worth watching is the price tag and the timing, because this is the kind of deal that would force Edmonton to part with real assets while also depending on Nashvilles willingness to reshape its own direction. The Predators have been linked to a broader reset, and if they decide to lean into that next chapter, the Oilers could find themselves in the middle of one of the summers most consequential trade discussions. [Read more 🡒]