The Edmonton Oilers, still reeling from their second consecutive Stanley Cup Final defeat, face a crucial offseason. General Manager Stan Bowman has publicly identified his top two priorities as the team sets its sights on a return to contention in the 2025-26 season. These priorities revolve around securing the long-term future of two key players: Connor McDavid and Evan Bouchard.

The first and arguably most significant task is negotiating a contract extension with Connor McDavid. The Oilers' captain and arguably the best player in the world is entering the final year of his current contract, which carries an average annual value of $12.5 million. McDavid becomes eligible to sign an extension on July 1st, and Bowman has made it clear that locking up the superstar is paramount. While McDavid has not explicitly stated a desire to leave Edmonton, the urgency stems from the risk of losing him to free agency next summer. The possibility, however remote, of McDavid testing the open market looms large, and Bowman aims to quell any uncertainty by securing a long-term commitment.

Negotiating with McDavid will be complex. He is due for a significant raise, potentially exceeding $15 million per year, which would place considerable strain on the Oilers' salary cap. Bowman must balance McDavid's value with the need to maintain a competitive roster around him. The length of the contract will also be a key factor. A long-term deal would provide stability but could limit the team's flexibility in the future. A shorter-term agreement might offer more financial breathing room but would require the Oilers to revisit negotiations sooner.

The second priority is re-signing Evan Bouchard, a restricted free agent (RFA) with arbitration rights. Bouchard has emerged as the Oilers' top defenseman and a crucial offensive contributor from the blue line. He is coming off a contract with a $3.9 million average annual value and is in line for a substantial raise. Like McDavid, Bouchard's new contract will significantly impact the Oilers' salary cap situation.

The Oilers currently have limited cap space, estimated at around $12 million. With McDavid and Bouchard both requiring significant raises, Bowman will need to find ways to create additional cap space. Potential strategies include trading players with unfavorable contracts, such as Evander Kane or Mattias Ekholm, or buying out contracts. These moves, however, come with risks. Trading away established players could weaken the roster, while buyouts result in dead cap space in future seasons.

Beyond these top priorities, Bowman faces other important decisions. Several depth players are set to become unrestricted free agents, and the Oilers will need to decide which ones to re-sign. The team may also look to bolster its forward depth through trades or free agency. Furthermore, the Oilers may consider changes in goal.

Ultimately, Bowman's success this offseason will depend on his ability to navigate these challenges while keeping the team competitive.