Should the Edmonton Oilers Trade Draisaitl if Extension Talks Fall Flat?

Leon Draisaitl Bob Frid-USA TODAY Sports

Leon Draisaitl answered questions from the Edmonton media last Wednesday that were focused on his current contract and plans for the future.

As the NHL superstar becomes eligible to sign an extension with the Edmonton Oilers on July 1, the franchise faces a critical decision: should they wait for Draisaitl to commit to the team or consider trading him if no agreement is reached by the end of summer?

"It's going to take time to figure out what I want and what the Oilers want,” Draisaitl told reporters.

Not prepared to let anyone in on what he’s contemplating, he said he hasn’t really thought about his contract all that much. The most he would give the fans and media was, "I love being an Oiler more than anything."

A follow-up question asked if that meant it was Edmonton first and everyone else second. He responded that, technically, the Oilers are the only team that can talk to him right now, so yes, it is Edmonton first.

Mark Spector of Sportsnet even laid out reasons to stay with the Oilers and said the media couldn’t find reasons worth leaving. Noting he would get paid, was on a contender, and his best friend was on the team, Spector asked if Draisaitl could think of a reason to leave.

The forward quipped, that when phrased that way, it is true, there isn’t much of a reason to go anywhere.

Meanwhile, with Ken Holland mutually parting ways with the team, the Oilers need a new GM. Sportsnet's Elliotte Friedman wrote on Saturday night the Oilers seem prepared to slow-play any contract extension talks with Draisaitl and not get too concerned if there aren't many answers to begin the month.

What Does Edmonton Do If Draisaitl Won’t Commit Soon?

Draisaitl, currently on an $8.5-million annual salary, is expected to command a substantial increase, potentially in the range of $13.5 million to $14.5 million per year. The money probably isn’t the issue since both sides know roughly what the player is worth. The real question becomes what Draisaitl thinks the chances are for Edmonton to get back to the Stanley Cup final and win. Is the team good enough? Is another team as likely to win and can potentially offer other features Edmonton fans and media aren’t considering?

Then, there’s the Connor McDavid issue.

With McDavid having an extra year on his contract, the duo's desire to stay together in Edmonton will be a significant factor in Draisaitl's decision. Maybe Leon wants to wait and see what the market has to offer in a year. Perhaps he’ll know better what McDavid intends to do as he fields offers from multiple teams. It would be hard to blame him for having all the facts and entertaining all ideas.

Draisaitl has emphasized that the process will take time, but it’s not clear yet if the Oilers are willing to give him all the time he might want.

The Oilers must consider their options carefully. On one hand, waiting for Draisaitl to decide gives them arguably the best chance to win again next season. Keeping this roster as close to whole as possible likely means Edmonton being a Stanley Cup favorite. It may also send a message to McDavid that the organization is willing to make next season a priority and give him the best chance to win a Cup.

On the other hand, waiting carries risks, particularly if Draisaitl ultimately chooses not to sign an extension. He could walk away with no assets coming back. If that happens, how likely is McDavid to stay knowing all the Oilers got in exchange was considerable cap space?

Any Real Thoughts to Trade Draisaitl Will Be Messy

Should the Oilers feel like they can’t risk the asset losing all value, trading Draisaitl is a scenario fraught with complications. Draisaitl has a 10-team trade list, effectively giving him significant control over his destination. From there, even if they can find a partner, the Oilers likely lose the trade, clearly giving up the best player. Edmonton can’t just acquire futures if they want to contend, but they can’t make a mistake and trade for the wrong players.

This situation mirrors that of Matthew Tkachuk from two years ago. The Calgary Flames thought they were doing well by trading Tkachuk for MacKenize Weegar and Jonathan Huberdeau. They immediately signed both to long-term extensions. The trade and the signings proved to be a huge mistake. Two years later, the Flames are rebuilding and the Panthers are the Stanley Cup champions.

Any potential trade involving Draisaitl would need to bring in promising or established players who are guaranteed to be contributors for seasons to come, and while the Oilers are in win-now mode. The odds of that happening are low. Maybe holding onto the player regardless of the outcome is the right play.

At the same time, it will be tough for Edmonton to convince itself to take the risk that Draisaitl could simply leave at the end of next season. A strategic trade could bring in assets that align with the team’s current needs. Getting nothing would be a tough pill to swallow, even if keeping Draisaitl ups the odds of a Stanley Cup in 2025.

The Oilers face a delicate balancing act. Waiting for Draisaitl to make a decision won’t be easy, even if it’s required.