What Connor McDavid's discount extension means for Oilers

What does this mean for the Oilers? 

After getting perhaps the biggest player discount in league history, they are now under immense pressure to win a Stanley Cup. The two-year length, which keeps McDavid in Edmonton until 2028, gives general manager Stan Bowman three seasons to get McDavid his championship. 

Bowman will need to upgrade the team in several areas: goaltending, depth scoring and defense. Let's take a look at the Oilers' cap situation for the next three seasons.

2025-26

Currently, the Oilers have just $834 in cap space and a roster size of 22, meaning, as of now, their lineup is set. They'll likely have to look to the trade deadline to make upgrades. One interesting note: both of their goaltenders, Stuart Skinner and Calvin Pickard, arguably the team's biggest weakness, are 2026 UFAs. Bowman may look to move one in a trade that lands them a better option in net.

2026-27

The good news for Oilers fans is that McDavid re-signed despite the team not making the needed upgrades for 2025-26. While it's not out of the question for Edmonton to make a third straight final, the Oilers are playing with fire heading into another season with Stuart Skinner in net. Additionally, with Western conference juggernauts like Dallas, Colorado and Vegas fine-tuning their lineups, another deep run could be a tough ask for the Oilers.

The 2026-27 season may be their best bet. Edmonton will have just over $22M in cap space and 14 players signed. The Oilers don't have any significant restricted free agents in line for big contracts and with Skinner and Pickard's contracts up, they'll have an opportunity to upgrade their goaltending.

The 2026 free agent class is loaded with talent, and the Oilers may be able to entice a player or two with the chance to play with McDavid and Leon Draisaitl. They'll also probably be able to sign arguably their best defender, Mattias Ekholm, to a cheap contract. He'll be 36 as a pending UFA in 2026 and is a good bet to see a smaller annual average value on his new contract than his current $6M per year.

2027-28

Lastly, we get to 2027-28. Once again, the Oilers are in good position cap and contract wise, with their core group of players (McDavid, Draisaitl, Zach Hyman, Ryan Nugent-Hopkins and Evan Bouchard) all signed. The salary cap will continue to rise, and Edmonton will have plenty of space to sign impact players.

However, if the Oilers don't win the Stanley Cup in either 2026 or 2027, there will be immense pressure on the group as McDavid heads into his last year of his new deal.

With this timeline, McDavid has sent the Oilers management a message: you have three seasons to address the needs of the roster or risk the best player in the world walking in free agency. 

By taking around a $6M-$7M dollar discount, McDavid gives Edmonton the cap flexibility to add to their roster. At just a two-year length, it's clear he sees these next three seasons as his best opportunity to win the Stanley Cup. 

As the salary cap continues to rise, hitting a potential $113.5M when McDavid will be a free agent in 2028, plenty of teams will be chomping at the bit to sign him to a record-setting deal. If the Oilers don't get the superstar his Cup by then, the rest of the league might get an opportunity to lure McDavid out of Edmonton.