Connor McDavid's next contract with the Edmonton Oilers is set to be one of the most closely watched negotiations in recent NHL history. As the league's premier player, McDavid's decision will not only impact the Oilers' future but also send ripples throughout the entire NHL landscape. Several key factors will weigh heavily on McDavid's ultimate decision.

1. The Oilers' Competitive Window:

Perhaps the most crucial element influencing McDavid's contract is his assessment of the Oilers' chances of winning the Stanley Cup in the coming years. McDavid has repeatedly stated that winning is his top priority. After two consecutive seasons ending in Stanley Cup Final losses to the Florida Panthers, McDavid needs to be convinced that the Oilers can maintain or even improve their competitiveness. He will want assurances that the team is committed to making the necessary roster adjustments and strategic improvements to become a perennial contender. This includes evaluating the performance of the team's management and coaching staff, as well as the development of young players and the acquisition of complementary talent. McDavid's agent, Judd Moldaver, is expected to engage in "broader discussions about the organization and direction" with Oilers' management, including General Manager Stan Bowman and CEO of Hockey Operations Jeff Jackson. McDavid himself has stated, "If I feel that there's a good window to win here over and over again, then signing is no problem."

2. Contract Structure and Length:

The structure and length of the contract will also be a significant consideration. While McDavid is expected to command the highest average annual value (AAV) in the NHL, the term of the contract could be a point of negotiation. A longer-term deal, typically eight years (the maximum allowed under the current CBA), would provide the Oilers with cost certainty and ensure McDavid remains in Edmonton for the prime of his career. However, McDavid might prefer a shorter-term contract, perhaps similar to the four-year extension Auston Matthews signed with the Toronto Maple Leafs. A shorter term would give McDavid more flexibility and allow him to re-evaluate his situation and potentially test free agency sooner if the Oilers' performance does not meet his expectations. The AAV will likely fall in the $15 million to $18 million range, depending on the term. The rising salary cap could also influence the final numbers.

3. The Supporting Cast and Team's Financial Flexibility:

McDavid's decision will also hinge on the Oilers' ability to build a strong supporting cast around him. The presence of Leon Draisaitl, who recently signed an eight-year, $112 million contract, is a major draw. However, the Oilers need to ensure they have enough cap space to retain other key players and add depth to the roster. This may involve making difficult decisions about other players' contracts, potentially trading away valuable assets to create financial flexibility. The Oilers are reportedly exploring options to shed salary by potentially trading players like Evander Kane and Viktor Arvidsson. The contracts of Evan Bouchard, Corey Perry and Trent Frederic will also need to be addressed. McDavid will want to be confident that the Oilers can maintain a competitive roster while also compensating him fairly.

In conclusion, McDavid's next contract will be a complex decision influenced by the Oilers' competitive outlook, the structure and length of the contract, and the team's ability to build a strong supporting cast. While Oilers fans are eager for McDavid to commit his future to Edmonton, McDavid is taking a measured approach, emphasizing that he is "in no rush" to make a decision. The coming weeks and months will be crucial as both sides navigate these critical factors to determine the future of one of hockey's greatest talents.