The Edmonton Oilers and Connor McDavid appear to be moving closer to a contract extension, but according to Oilers CEO Jeff Jackson, the negotiation process feels different than Leon Draisaitl's extension last year. McDavid, who has one year remaining on his current deal worth $100 million signed in 2017, has been eligible to sign an extension for nearly two months.

Jackson addressed the situation, stating that the negotiation "won't be a long negotiation". He conveyed confidence that a deal will be reached when McDavid is ready to discuss it, emphasizing McDavid's comfort in Edmonton, his love for the team, and the team's consistent competitiveness. "There's a sort of comfort with Connor [McDavid]. He's been in Edmonton for 10 years, he loves playing for this team," Jackson said. He also noted that the conversation surrounding the contract would be different if the team were struggling.

Jackson drew a comparison to Leon Draisaitl's contract extension from the previous year, recalling the heightened media pressure and talk surrounding that negotiation. Draisaitl signed his extension in early September 2024 without drawn-out discussions, and Jackson anticipates a similar, smooth process with McDavid. "[W]e got a deal done early September with Leon, and super happy about that. I feel it's the same with McDavid,” Jackson stated.

Several reports suggest that an agreement could be reached soon, potentially before the start of training camp in September. McDavid is scheduled to participate in Canada's Olympic Camp from August 26th to 28th, and the Oilers' training camp commences on September 8th in Sherwood Park, Alberta. This timeline presents a window of opportunity for both sides to finalize the extension.

Insider Elliotte Friedman speculated that discussions will intensify between the Olympic camp and training camp. "I would expect after Connor McDavid is done there and he goes back to Edmonton, they will work on getting this done,” Friedman said. The organization reportedly intends to make a formal announcement with a press conference at Rogers Place.

While the exact terms of the contract remain undisclosed, speculation suggests McDavid's new deal could be in the range of $16 million to $17.5 million per year for a term of three to four years. Frank Seravalli predicted the deal would land "somewhere between $16 million and $17.5 million a year for four years". With approximately $45 million in projected cap space for the upcoming summer, the Oilers are financially positioned to accommodate McDavid's significant raise.

McDavid himself has emphasized the importance of winning, stating that his decision to sign an extension hinges on his belief in the team's ability to contend for the Stanley Cup. "If I feel that there's a good window to win here over and over again, then signing is no problem," McDavid said. Despite recent playoff disappointments, including a loss to the Florida Panthers, the Oilers have reached the Stanley Cup Final two years in a row. The team's management and ownership have expressed their full support for McDavid, and they are committed to building a championship-caliber team around him.