Leon Draisaitl Signs Record-Breaking 8-Year Extension What Does This Mean for the Oilers?

A much-anticipated keep was made official in Edmonton this past Tuesday.

Superstar Leon Draisaitl, who was set to be a restricted free agent next summer, signed an eight-year, $112 million extension to keep him with the Oilers through the 2033 season, making him the NHL’s highest-paid player with an average annual value of $14 million, as initially reported by Sportsnet’s Elliotte Friedman.

The contract is the second-largest in terms of total value in NHL history, behind only Alex Ovechkin’s 13-year, $124 million contract with the Washington Capitals signed under the previous Collective Bargaining Agreement in 2008. Draisaitl’s contract contains a full no-movement clause for the entire contract, per TSN’s Pierre LeBrun. The deal also includes a front-loaded structure, though the salary breakdown has yet to be reported.

It was widely anticipated that Draisaitl signs a max-term extension to stay with the Oilers, but few were thinking of him to be the first player to land a $14 million cap hit, let alone surpass Auston Matthews’ $13.25 million cap hit to become the league’s newest highest-paid player.

Table of Contents

1 Leon Draisaitl Gets His Money’s Worth for His Production

Leon Draisaitl Gets His Money’s Worth for His Production

Draisaitl is one of the key faces of the NHL, though he wasn’t an instant impact piece when he first arrived to the NHL. After nine points in 37 games in his post-Draft year, he developed into a high-end top six piece, routinely hitting over 20 goals and 70 points. But the 2019 season was his first true breakout campaign, where he led the team in goals (50) and finished second in points behind Connor McDavid, with 105. Since that season, the Oilers have made the playoffs every year, and he’s recorded or on pace for over 100 points in a full 82-game season.

He is also one of the most prolific playoff performers in NHL history, ranking 4th all-time in points per game among players with at least 50 games of playoff experience, at 1.46 points per game, only behind McDavid (1.58), Mario Lemieux (1.61), and Wayne Gretzky (1.84). Even more impressive to this is that Draisaitl has played through multiple injuries through several portions of the last three playoffs.

Of course, it’s not just about the money. The Oilers also have a measure of pride that they compelled Draisaitl to forego unrestricted free agency. It speaks volumes, from ownership to the front offices, to the people working on and off the ice. More than all of that, though, it speaks to Draisaitl’s belief that he can win a Stanley Cup for several seasons in Edmonton.

And as such, the Oilers are intent on giving it their all for winning a Cup in 2025. They fell one game short of their first Stanley Cup in over 30 years just over two months ago, and they want to do everything they can to finish the job this time around. It also, in turn, sets up the Oilers for McDavid’s next deal and a blockbuster contract for top offensive defenseman Evan Bouchard before next summer. Keeping two superstar centers and a high-end no. 1 defenseman is paramount for the Oilers.

Connor McDavid and Leon Draisaitl are Intent on Winning Together

“Leo and I have been here our whole careers. We’ve been through some bad years. Some disappointments,” said McDavid last year when asked of trying to win a Stanley Cup with Leon Draisaitl. “But at the same time, I look at the culture that we built here. Where the organization sits today, and I take a lot of pride in that. Our core here has built something, really from the ground up. We take a lot of pride in that. To see it through with the people that have been here the whole time, that’s what it’s about.”

Both McDavid and Draisaitl believe that their chances at winning the Stanley Cup are at their greatest if they remain teammates, and why it’s different than just winning the Stanley Cup in general.

The chances of McDavid remaining with the Oilers if Leon Draisaitl left for free agency were slim. McDavid could convince someone to play with him in Edmonton before Draisaitl left, but to replicate the same production that Draisaitl provides is extremely difficult, if not impossible. The Oilers have built this current team from the ground up, and came one win short of the ultimate prize. And both McDavid and Draisaitl want to realize that dream come true for themselves together.

Ken Holland Laid the Groundwork of the Foundation

It was a badly kept secret that Holland’s time in Edmonton was going to end after 2024. A month later, they officially hired Stan Bowman, who is seeking to repair his reputation after the fallout of the Chicago Blackhawks’ sexual assault scandal, as their general manager.

The work on Draisaitl’s contract dated well before Bowman’s arrival, despite that it was signed under his tenure. However, it was Holland who built the groundwork to set up the Oilers for these critical contracts.

The thing is, Holland has been a mixed bag of sorts since the lockout of 2005 dating back to his Detroit Red Wings years. His salary cap management is going to leave the Oilers cap-strapped annually. And while the Darnell Nurse overpayment is going to be talked about on a yearly basis, the Oilers wouldn’t be contending for a Stanley Cup if it weren’t for Holland giving out extremely reasonable contracts to Zach Hyman and Ryan Nugent-Hopkins, along with trading for players like Mattias Ekholm, Adam Henrique and Brett Kulak.

It’s fair to question if another general manager would have already delivered Stanley Cups to McDavid and Draisaitl, and Bowman is going to be testing that question. However, it wasn’t that long ago when the Oilers were a complete mess. Holland did all he could to set them up for success.

The Oilers are in a Tight Cap Situation Next Summer

Even after declining to match the offer sheets for Dylan Holloway and Philip Broberg, the Oilers are in a very serious cap situation for next summer. They already have a projected cap hit of $77.4 million, leaving them with $14.6 million to re-sign pending RFA Bouchard and fill at least three other roster spots, assuming the upper limit is $92 million. 38.9% of the cap is already accounted for McDavid, Draisaitl, and Darnell Nurse.

The intentions are clear: Cup or bust. This season will likely be the last great shot the Oilers have, and they’ll need to get their steps back on their way to the Stanley Cup Final. They are more than capable of scoring their way there after reloading offensively with key names like Jeff Skinner and Viktor Arvidsson added via free agency.

Question marks remain on the defense outside of the pairing of Bouchard and Ekholm. While the defensive structure has improved under Knoblauch and Coffey, there’s not a lot of stability behind them, and while Ty Emberson is a cost effective replacement for Cody Ceci, declining play from Nurse is a significant concern.

This season will be the last year of Draisaitl’s current contract, earning $8 million in actual salary of the eight-year, $68 million deal he signed coming off his entry-level contract.

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