Six proposed Edmonton Oilers trades that did not go through

Over the years, there are bound to be a collection of moves, signings, and trades that didn’t quite make it to the finish line. For whatever reason, sometimes internal politics other times for obvious reasons, like the proposal being the type that would cause the GM to lose all of their phones were it an old NHL Be a GM mode offer.

Some of these absolutely wild trade proposals are widely known. Some trades are clearly initial proposals that never had a chance to be accepted, but still were put out into the world. But regardless, all of them are crazy offers that would have had a drastic impact on this team’s trajectory, even to this day.

For a bit of fun this quiet offseason, let’s revisit some of the more prominent almost roster moves from Edmonton Oilers history.

Leon Draisaitl to the Tampa Bay Lightning?

Back in 2019, the Tampa Bay Lightning were fresh off of getting swept in the first round by the Columbus Blue Jackets and clearly looking to make changes. The core of the team needed to be shaken up in some way to find the right combination to finally stop disappointing in the playoffs.

During the offseason that year, Jeff Marek recently revealed that the Lighting and Oilers were in active talks about swapping Leon Draisaitl for Nikita Kucherov, the Lightning superstar that had won the Hart Memorial Trophy, Ted Lindsay Award, and Art Ross Trophy the previous season.

This would have been an absolutely groundbreaking shake-up for both teams.

Draisaitl was just coming into his own as an NHL star, with his first 50-goal and 100-point season that saw him finish as the runner-up for the Rocket Richard Trophy. Kucherov was just ahead of Draisaitl in the development curve, having established himself a season prior with a 100-point campaign.

Reportedly, the Oilers also wanted Anthony Cirelli, though it is unclear if that was a sticking point that caused the deal to fall through or was a separate plan for Edmonton.

Regardless, this would have gone down as one of the biggest trades in NHL history. Shortly after this trade proposals fell through, both Draisaitl and Kucherov fully established themselves as top-five players in the league. It is crazy to think about how things would have been different had this happened.

Draisaitl and Connor McDavid have become one of the most iconic dynamic duos the league has seen with a one-two punch down the middle that eclipses any other team’s centre depth. While the Lightning figured it out right after this and won two consecutive Stanley Cups with Kucherov.

Mike Comrie for Corey Perry

Nearly 20 years before Corey Perry actually joined the Oilers, he was almost traded to Edmonton. In a trade that would have swapped two, at the time, promising young prospects.

Back in 2003, Comrie had begun to wear out his welcome in Edmonton. The young forward had already been taking advantage of loopholes to become a free agent early and sign bigger contracts than what he would have been allowed to otherwise. He was then locked in another contract dispute before the 2003–04 season, leaving him holding out through the preseason and well into tthe regular season. He then requested a trade.

Then-GM Kevin Lowe, after many rounds of negotiations with the Anaheim Ducks, finally had an agreeable offer on the table, and Comrie had agreed to a contract with the Ducks. That trade package would have brought Perry and a first-round pick to Edmonton.

Only problem, the trade didn’t happen. Reportedly because Kevin Lowe wanted Comrie to repay the Oilers a $2.5M bonus that was paid to the player that past offseason. Yes, Lowe wanted the player to pay the team back. What isn’t known is if this was a move of petty vindictiveness or because the Oilers in that era were having financial difficulties and needed the money for other players.

This trade did not happen and Comrie was shortly after traded to the Philadelphia Flyers. The trajectory of the team could have changed significantly if a player of Perry’s calibre joined the Oilers for a lengthy career.

All-Star Dany Heatley blocks the Oilers

In 2009, the Oilers were in shambles. The team was stuck, struggling, and declining with no amount of bold moves or contracts leading to barn fight offers creating enough change to turn things around. There was one final, last ditch attempt to acquire a big name player after the signings of Tomas Vanek and Michael Nylander had fallen through in the previous seasons. And that was to trade for the all-star himself, Dany Heatley.

Heatley had worn out his welcome in Ottawa and the team was looking to move on from the former 50-goal, 100-point forward after his worst season with the Senators the year prior. He had 39 goals and 72 points. Rumblings suggested that he would be willing to waive his no trade clause to go to Edmonton, and the city was ecstatic. A legitimate star player to play with Ales Hemsky? Fantastic.

A deal was made and agreed to by both teams. Heatley would come to Edmonton while the Oilers would send Dustin Penner, Andrew Cogliano, and Ladislav Smid in return.

At the last minute, Heatley vetoed the deal and refused to waive his NTC, canceling the deal. He would end up being sent to San Jose instead.

That may have been the better outcome. An expensive winger who had one more high level season, recording 82 points in his first year with San Jose, before regressing, getting traded to Minnesota after his second year with the San Jose Sharks, and never re-finding his game.

Ultimately, Penner was traded to the Kings after a career year in a deal that brought the pick used to select Oscar Klefbom. Cogliano was also traded shortly after elsewhere. And Smid was a beloved, reliable, defensive defender for a few more years and has become a prominent member of the Oilers alumni in the community.

Draisaitl (again) but to the Montreal Canadiens this time

Luckily there are no indications that this trade offer was seriously considered or went anywhere because it would have absolutely ruined any plans the Oilers had at building a competitive team.

After the 2015–16 season, both the Oilers and Montreal Canadiens had been looking to make some tweaks that would put them over the top. The Oilers were in desperate need for defence at the time, with a defensive group led the previous season by Andrej Sekera, Darnell Nurse and Oscar Klefbom still in their early 20s and developing, and a bunch of depth role players filling the rest out.

That is where the appeal in a possible trade for superstar defender P.K. Subban comes into play. He was one of the most recognizable and dynamic players in the league, two seasons removed from a Norris Trophy. And would immediately reshape the identity of the Oilers’ defence.

As we know, the Habs were interested in moving him at the time where he (thankfully) later ended up with the Nashville Predators. But before that, there was a reported trade offer to send him to Edmonton. And it was an absolute haul for Montreal.

The trade would have seen Draisaitl, one of Klefbom or Nurse, a first-round pick (likely the fourth overall that was used to select Jesse Puljujarvi), or one other unnamed prospect. All for penalty kill Subban.

At the time, Draisaitl was not the calibre of player he is now, nor was he expected to turn into that. He had already been a productive player, with a 52-point season in his second year in the league, however. Klefbom was shaping up to be a top-pairing defender until injuries forced him into early retirement, while Nurse has been a big part of the team’s core for the past decade.

Giving up that much for what really amounted to two or three more good seasons of Subban would have set the Oilers on the wrong trajectory at the beginning of the McDavid era. And we are extremely grateful that this offer was shot down pretty quickly and did not go anywhere.

A different one-for-one Taylor Hall trade

Everyone knows about the “the trade is one-for-one” joke that was created from a tweet by the legendary Bob McKenzie following the Taylor Hall for Adam Larsson trade (which I still maintain wasn’t as bad as it gets panned for). What ended up as one of the most made-fun-of trades in Oilers history could have been even worse if the initial target had panned out.

There have been a few different versions of this trade proposed. One sent him to the New York Islanders in exchange for Travis Hamonic, but luckily the Islanders were unwilling to part with him at the time.

The one that will get featured here will bring another (now former) Oiler to the organization years before their tenure even started. And that player is none other than Cody Ceci.

Ceci, at the time, had just finished his second full season in the league and had a career high 26 points. Former GM Peter Chiarelli, in his desperation to find a defender, was pursuing him to help add a promising young defender.

The rumoured hang-up on this trade was it requiring approval from Ottawa’s ownership. By the time that process could end, Hall was traded to the New Jersey Devils.

That was certainly a best case scenario as in the following years, Ceci did not develop much further and would not have been the player the Oilers thought they were acquiring.

Trade the entire team?

Perhaps the wildest hypothetical trade that didn’t actually happen (thankfully) is the time in the 1980s that the Oilers and Toronto Maple Leafs nearly traded cities. Like, everything.

The Oilers would have moved to Toronto, while the Maple Leafs would have come to Edmonton in this crazy near-deal proposed back in 1980, according to a recounting from Peter Pocklington himself in his book about his time as the owner of the Oilers.

Talks had progressed and had reached a point where it may have happened. Maple Leafs owner Harold Ballard also wanted $50M in cash to go along with the move to help alleviate financial troubles that he was having.

Luckily for us in Oil Country, Ballard backed out of the deal and it did not happen. Within five years, the Oilers had developed into one of the greatest dynasties in NHL history to help make Edmonton one of the most storied and successful franchises around. The Maple Leafs, on the other hand, were in the middle of having their roster gutted for a miserable decade in the 80s that resulted in their best season being in 1989–90 with a .500 points percentage (38–38–4 record).