Tick… tick… tick… That sound you are hearing is the clock counting down on Connor McDavid’s time with the Edmonton Oilers [https://thehockeynews.com/nhl/edmonton-oilers]. Yes, McDavid put off becoming a UFA by signing a very team-friendly extension on Monday [https://thehockeynews.com/news/latest-news/oilers-connor-mcdavid-announces-monumental-contract-extension]. But he didn’t put it off for very long. The two-year, $25-million contract kicks in next season, which means the Oilers now have three more years [https://thehockeynews.com/news/latest-news/the-oilers-are-clearly-on-the-clock-with-connor-mcdavid-s-contract-extension] to prove to their captain that they can finally get over the hump and win a championship. Or, at the very least, they have to prove that this team is built for long-term success. If not, McDavid could be a UFA as early as July 1, 2028. As everyone in Toronto knows, 2028 is pretty significant because it’s also when Auston Matthews’ current four-year deal expires. Coincidence? Well, consider that McDavid and Matthews both share the same agent. In other words, if McDavid [https://thehockeynews.com/nhl/edmonton-oilers/latest-news/stan-bowman-details-behind-the-scenes-of-mcdavid-extension-that-s-what-connor-wanted] ends up choosing to leave Edmonton in three years, we know that there could be at least one other team that will have the cap space to sign him — and vice versa for Matthews [https://thehockeynews.com/news/latest-news/a-healthy-auston-matthews-is-prepared-to-guide-the-maple-leafs-and-prove-last-year-was-an-outlier] and the Oilers. That is, unless Toronto [http://thn.com/toronto] is in an even worse spot than Edmonton by then. Either way, the Oilers have three years and some extra cap space to win it all and set themselves up for future success. “He wants to win, and that’s what it comes down to,” former Oilers goalie Devan Dubnyk said on The Hockey News’ Big Show on Monday. “Pressure on the Oilers now. The Hockey News Big Show: Breaking Down McDavid’s Extension And Previewing The Pacific [https://deweb-519a7.b-cdn.net/post-images/8fecf71b-095d-442b-94d8-1d81263c1a3d.jpeg] The Hockey News Big Show: Breaking Down McDavid’s Extension And Previewing The Pacific <b>The Hockey News Big Show is here with former longtime NHL goalie Devan Dubnyk to preview the 2025-26 NHL season for each team in the Pacific Division. But first, they have big news to discuss on the contract front.</b> [https://thehockeynews.com/news/podcast/the-hockey-news-big-show-breaking-down-mcdavid-s-extension-and-previewing-the-pacific#google_vignette] “He’s given them the most team-friendly contract ever for a player that could be demanding $20 million a year for eight years. What he’s saying is that he believes in the team in the short term for now that they can win a Stanley Cup. And he’s giving the Oilers [http://thn.com/edmonton] the flexibility to go out and get pieces to fill in and do that. It’s just showing that his priority is winning now. “Obviously, three years down the road, he can cash in and get whatever he wants.” Indeed, three years from now could be a watershed moment for the NHL. If you thought this summer was monumental with Kirill Kaprizov [https://thehockeynews.com/nhl/minnesota-wild/community/latest-news/does-mcdavid-taking-less-make-kaprizov-s-17-million-look-like-an-overpay]setting a new bar by signing an eight-year extension with a cap hit of $17 million, just wait until 2028. That summer, McDavid and Matthews could be hitting the open market together. If it happens, they probably won’t be looking for team-friendly deals. Not with the salary cap expected to rise from $95.5 million this season to $104 million in 2026-27 and then $113.5 million in 2027-28. By 2028-29, when McDavid and Matthews could be free agents, the cap could be well over $120 million. The Oilers Are Clearly On The Clock With Connor McDavid's Contract Extension [https://deweb-519a7.b-cdn.net/post-images/a63dcfcd-0943-44de-8aaa-9b9bcb57f8f2.jpeg] The Oilers Are Clearly On The Clock With Connor McDavid's Contract Extension So Connor McDavid, the best hockey player on the planet, willingly <a href="https://thehockeynews.com/news/latest-news/oilers-connor-mcdavid-announces-monumental-contract-extension">chose to give himself a zero percent raise</a> and give himself the third-highest cap hit in the NHL when he could have blown everybody out of the water. [https://thehockeynews.com/news/latest-news/the-oilers-are-clearly-on-the-clock-with-connor-mcdavid-s-contract-extension] Whatever money McDavid left on the table by signing for the same average annual value as his current deal will likely be recouped three years from now. If so, we could be looking at a scenario where McDavid’s and Matthews’ cap hits are more than $25 million each. Who knows, maybe McDavid will be signing for that amount in Edmonton. And maybe Matthews will be signing a similar deal in Toronto. It all depends on where the Oilers [http://thn.com/edmonton] and Leafs [http://thn.com/toronto] are at that time — and what they have accomplished up until that point. If the Oilers are forever the bridesmaids and still losing in the final with a watered-down roster and the Leafs are still stubbing their toes in the second round, then maybe McDavid and Matthews will take their talents elsewhere. And because both could be free agents at the same time, don't rule out the possibility of them joining forces and trying to win a championship together. The countdown begins now. For action-packed issues, access to the entire magazine archive and a free issue, subscribe to The Hockey News at THN.com/free [https://thehockeynews.store/products/print-subscription]. 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