The Edmonton Oilers face a crucial offseason in 2025, coming off another heartbreaking Stanley Cup Final loss. General Manager Stan Bowman has a busy agenda to keep the team competitive while navigating the complexities of the salary cap. Here's a breakdown of the key tasks:

1. Connor McDavid's Extension: The undisputed top priority is securing Connor McDavid to a long-term contract extension. McDavid is eligible to sign a new deal on July 1st and is entering the final year of his current contract. The organization hopes he will follow Leon Draisaitl's path and commit to Edmonton for another eight seasons. While McDavid has stated he's in "no rush" to make a decision, the Oilers are eager to begin negotiations. Securing McDavid long-term would provide stability and reassure fans that the team's cornerstone player is committed to bringing a Stanley Cup to Edmonton.

2. Evan Bouchard's New Contract: Another critical task is re-signing Evan Bouchard. As a restricted free agent, Bouchard is due for a significant raise after becoming one of the league's most productive defensemen. His offensive contributions from the blue line have been invaluable, especially during the Oilers' playoff runs. Some analysts predict his next contract could carry an annual value of $10 million or higher. Locking up Bouchard long-term is essential to maintaining a strong defensive core.

3. Navigating Free Agency: Several Oilers players are set to become unrestricted free agents, including Corey Perry, Connor Brown, Jeff Skinner and John Klingberg. Bowman has expressed interest in re-signing Trent Frederic and is in talks with Perry and Brown. Deciding which of these players to bring back will depend on their performance, fit within the team's system, and, crucially, their contract demands.

4. Salary Cap Management: The Oilers have approximately $11.96 million in cap space. However, with McDavid and Bouchard needing new contracts, strategic decisions must be made to maximize the team's financial flexibility. The Oilers also carry $2.55 million in dead money against the cap, including $2.3 million from the Jack Campbell buyout and $250,000 from Corey Perry's performance bonus overage.

To create additional cap space, the Oilers are reportedly looking to trade Evander Kane and Viktor Arvidsson, both of whom have one year remaining on their contracts. Buying out players like Kane, Arvidsson or Mattias Janmark could also free up cap space, albeit with long-term financial implications.

5. Addressing Goaltending: The Oilers' goaltending situation remains a question mark. While Stuart Skinner has shown flashes of brilliance, his performance has been inconsistent. Bowman might explore the trade market to acquire a more established starting goalie or a reliable tandem partner for Skinner. Potential trade targets could include John Gibson.

6. NHL Draft 2025: The Oilers have limited draft capital in the upcoming 2025 NHL Draft. They are without their first-round pick, which belongs to the Philadelphia Flyers. Their first selection is in the middle of the third round as compensation from the St. Louis Blues for signing restricted free agent Dylan Holloway last summer, and they also have their own sixth- and seventh-round picks. The team has already traded away their first-round pick in 2026. Given these limitations, it seems unlikely that Edmonton will trade to move up in the draft.

7. Potential Buyouts With limited cap space, the Oilers may look to the buyout market. Evander Kane and Viktor Arvidsson are potential buyout candidates, with the team saving $2.67M in 2025–26 and having a $1.33M penalty in 2026–27 if either is bought out. Mattias Janmark is a cheaper buyout option, but he would only save the team slightly more than $1M next season and $717k the season after.

In conclusion, the Oilers' 2025 offseason presents a complex set of challenges and opportunities. Securing McDavid and Bouchard long-term while strategically managing the salary cap will be critical to ensuring the team remains a Stanley Cup contender for years to come.