Leon Draisaitl’s contract already looks like a bargain for the Oilers

Draisaitl’s first contract had Oilers fans nervous. It was a big commitment, a lot of money for a player who hadn’t even posted a point-per-game season in the NHL yet. People criticized then-GM Peter Chiarelli for not getting Draisaitl signed at a number closer to what guys like Nathan MacKinnon or David Pastrnak were making at the time, both under $7 million annually.

But that contract aged well, quickly. Draisaitl would go on to produce at a 100-point pace in seven of the eight years and was consistently viewed as one of the best-value contracts in the NHL.

I’m not sure if an eight-year deal for Connor McDavid is going to be possible. At the end of the day, there might not be much of a negotiation.

If McDavid wants to sign for three, four, or five years, then that’s what the Oilers are going to have to offer. They can lay out all sorts of plans, but if he wants $18 million per season, they’ll have to give it to him.

He holds the cards, and in some ways, he has a blank cheque.

Still, it’s no secret the Oilers would love to sign him to a max-term deal. This is the last offseason in which McDavid (or any NHL player) can sign an eight-year contract, with term limits set to change under the new CBA.

Even if McDavid came to them and said he’d only sign eight years at $19 million AAV, the Oilers should absolutely take that deal. Cutting the term down to three or five years just to save $2-3 million per season is not worth it.

The goal should be simple. Get the full term, no matter the cost. McDavid will always provide surplus value, and locking him in through 2034 could turn this next deal into a steal by the back half, especially as the salary cap continues to rise.

That kind of forward-thinking approach is something the Oilers have lacked at times, and it’s cost them.

Look no further than the Darnell Nurse situation. Most fans don’t dislike the player, they hate the cap hit. But that number only got that high because the team kept bridging him instead of committing long-term.

When they finally signed him to the current eight-year deal, he was a year away from UFA status and held all the leverage. Letting him walk wasn’t an option, especially with all the Toronto rumours and his Kyle Dubas connection, so the Oilers had no choice but to pay top dollar.

But imagine if they’d signed him long-term back in 2020 instead of giving him a two-year, $5.6 million bridge deal. They were tight to the cap at the time, sure. But what if they had locked him in around $7.5 million?

That number would look much more manageable today, and the deal would be aging just fine.

It’s the same story with Evan Bouchard.

In 2023, the Oilers bridged him with a two-year, $3.9 million AAV deal. But what if they’d offered him a full eight-year, $8 million extension right then?

Would Bouchard’s camp have said no to $64 million in guaranteed money? Doubtful. And with how he’s playing now, he’d already be exceeding that value, with six years still left on the deal.

Instead, the Oilers are paying him $10.5 million per year on a four-year deal, and they’ll likely have to pay even more to keep him when he hits UFA status.

Sure, I’m making some assumptions here, and hindsight is always 20/20. But the Oilers’ reluctance to commit to Nurse and Bouchard early has already cost them, and will continue to do so.

Some will argue that cap space was too tight to go the long-term route, and that’s fair. But that brings us back to the bigger issue, which is organizational philosophy.

The Oilers’ real mistake wasn’t committing to Nurse or Bouchard, it was committing to depth pieces like Kris Russell and Zack Kassian at inflated prices. They locked in their role players before locking in their core. That’s where the cap missteps happened.

Compare that to the Florida Panthers. They lock in their key guys and rely on strong pro scouting to round out the bottom six and third pairing with value deals.

They don’t overpay players who aren’t true difference-makers. The Oilers have been guilty of that.

And look, let’s not forget that the Oilers have made it to back-to-back Stanley Cup Finals, so you won’t hear me complain much about how the team’s been run the last two seasons.

But if they want to keep this window wide open for the next eight years, some things need to change. Commit to good players early, give them term, and let the value take care of itself.