The Edmonton Oilers made a big splash on Tuesday, signing Leon Draisaitl to a monster extension. The $14 million average annual value (AAV) is the highest in league history and creates a salary cap crunch for new general manager Stan Bowman. Superstar and captain Connor McDavid is eligible for an extension next summer, something Draisaitl addressed with TSN's Chris Johnston.

“Leon Draisaitl hopes his #oilers extension will be followed by one for Connor McDavid next summer,” Johnston posted on social media, “but adds: ‘Connor's going to do what's best for him, right? That's just the way this works and it's supposed to work that way. I did what I thought was best for me personally.'”

That is the question that is answered by teams and players in every salary cap league. Draisaitl decided he wanted the most amount of money possible. The Oilers decided they wanted to try and keep the band together. Everyone will cite Tom Brady's team-friendly deals as the mark of a great teammate, but that does not work for everybody.

It would be stunning if McDavid gets to unrestricted free agency. A player of his caliber has never reached free agency in the history of the NHL. While Wayne Gretzky changed teams and Artemi Panarin is the best modern example, McDavid is on another level. Do not expect your favorite team to be placing a bid on number 97 come 2026.

Expectations for Leon Draisaitl, Connor McDavid, and the 2024 Oilers

Edmonton Oilers forward Connor McDavid (97) and forward Leon Draisaitl (29) and defenseman Evan Bouchard (2) during a stop in play against the Vancouver Canucks during the first period in game five of the second round of the 2024 Stanley Cup Playoffs at Rogers Arena.
Bob Frid-USA TODAY Sports

The Oilers came painfully close to a historic comeback in the 2024 Stanley Cup Final. After going down 3-0, they won three straight games to force game seven. They lost that game and are looking to get back in 2024-25. Having Draisaitl locked up long-term will help but they need great performances from depth forwards again.

Jeff Skinner was signed to a one-year deal and Matthew Savoie was traded from the Sabres to make those contributions. While there were pieces lost, they replaced them with good value deals to keep their championship hopes alive. While McDavid and Draisaitl are two of the best players in the world, they need to score when they are off the ice too.

McDavid will likely break Draisaitl's AAV record when he signs his new deal. Whether that is next summer or when the deal is up in 2026, the best player on Earth will be compensated as such. He held the record for multiple years at $12.5 million, but that was broken by Nathan MacKinnon in 2022 at $12.6. Auston Matthews topped the list at $13.25 until Tuesday.

If and when McDavid signs his extension with Edmonton, the cap will become quite the balancing act for the Oilers. They struggled to have solid goaltending and depth play in the early years of their current deals and that could continue when the new deals kick in. Bowman's job will be to ensure they have a balanced roster for years to come.

Bowman was able to make it work with two large contracts on the books with the Chicago Blackhawks. Jonathan Toews and Patrick Kane were two of the highest-paid players in the league and they were still able to win three Stanley Cups.