Remember when Connor McDavid signed his contract?

<a href="https://oilersnation.com/news/connor-mcdavid-officially-signs-eight-year-100-million-contract">It was early July in 2017</a>. The Oilers had just ended a decade-long playoff drought, thanks largely to a Hart and Art Ross Trophy-winning campaign from their 20-year-old captain.
After just two seasons and 127 games in the NHL, Edmonton&#8217;s front office had no qualms making an eight-year, $100 million commitment to the first-overall pick from the 2015 draft. Already arguably the best player in the league, McDavid would surely lead the Oilers to glory very soon.
In the subsequent years, despite 224 points over 160 games from the young phenom, Edmonton missed the playoffs in both 2017-18 and 2018-19. The team slowly built into a serious contender through the course of <a href="https://oilersnation.com/news/connor-mcdavid-leon-draisaitl-locked-up-for-the-next-eight-years">McDavid&#8217;s eight-year deal</a>, but, entering the contract&#8217;s final season in 2025-26, the Oilers still don&#8217;t have a Stanley Cup.
With the benefit of hindsight, maybe he would have handled his second contract differently. Those lost seasons are likely being considered in the negotiation for contract three.
<a href="https://www.tsn.ca/nhl/connor-mcdavid-says-confidence-in-edmonton-oilers-has-never-been-higher-1.2355239">When McDavid spoke with TSN&#8217;s Ryan Rishaug on Thursday</a>, he stressed his confidence that the Oilers can win the Stanley Cup this season. Beyond that? Let&#8217;s just focus on this year.
<blockquote>“My confidence in this team this year has never been higher. That&#8217;s what I can say about that.
Listen, does anyone have a crystal ball and know what two years, three years, four years, five or whatever (will look like)? Nobody has a crystal ball. Nobody knows what that&#8217;s going to look like. The belief is not the issue, not that there is an issue. It&#8217;s just that we&#8217;re working through it and we&#8217;re working through it together. I think Jax (Jeff Jackson) said we&#8217;re trying to find a razor’s edge and part of that’s true. We’re trying to find a scenario that works for everybody in terms of my family, my family’s security, a deal that makes sense for the team to continue to have success.
My belief in this season and the players this year has never been higher.”</blockquote>
After consecutive trips to the Cup Final that resulted in losses to the Panthers, the Oilers again appear poised to come out of the Western Conference. They plowed through the L.A. Kings, Vegas Golden Knights, and Dallas Stars with an impressive 12-4 record before falling in six to Florida.
But that&#8217;s this year. What about beyond that? How do the Oilers look through the rest of the decade? It&#8217;s difficult to say how veteran forwards like Zach Hyman and Ryan Nugent-Hopkins will perform in their mid-30s. It&#8217;s already difficult to say if the team can still lean on 35-year-old Mattias Ekholm to be a top-pairing defenceman. And, of course, there&#8217;s the <a href="https://oilersnation.com/news/edmonton-oilers-stuart-skinner-new-goalie-coach-goal-play-team-canada-stanley-cup">goaltending situation</a>.
Oilers CEO and McDavid&#8217;s former agent, Jeff Jackson, went on the radio earlier this week to <a href="https://oilersnation.com/news/edmonton-oilers-ceo-jeff-jackson-discusses-connor-mcdavid-contract">pour water on any smoke</a> that the team&#8217;s star player is headed for an exit. Jackson added that he and McDavid’s new agent, Judd Moldaver of Wasserman Hockey, had talked for over an hour earlier about potential contract options, reinforcing that his former client is taking his time to weigh multiple options.
All signs seem to point to McDavid signing another contract with Edmonton, but it also seems inevitable that this isn&#8217;t another eight-year pact. The goal isn&#8217;t to constantly re-sign for more money alongside a rising salary cap; the goal is not to be stuck on a team that isn&#8217;t competing for the Stanley Cup.
<blockquote>&#8220;I think guys within the Edmonton market understand what my desires are because they know me. The players understand where I&#8217;m at,&#8221; <a href="https://www.tsn.ca/nhl/connor-mcdavid-says-confidence-in-edmonton-oilers-has-never-been-higher-1.2355239">McDavid told Rishaug</a>. &#8220;It&#8217;s not about trying to make the most amount of money. I think my former agent knows that, given how has the last negotiations went.
It&#8217;s about winning. It&#8217;s about winning over and over again and that&#8217;s my priority. All with the understanding that I put a lot into this. It&#8217;s been 25 years of putting a lot of everything I have into this, and my family deserves that security, they deserve the lifestyle that being a pro hockey player and being very good at it and all the work that goes into it deserves. So, it is trying to find a balance.&#8221;</blockquote>
None of this reads like McDavid is ready to rush out the door to join his childhood Toronto Maple Leafs on a quest to get beyond the second round of the Stanley Cup Playoffs for the first time since the early years of the George W. Bush administration. It&#8217;s that he wants the flexibility to <a href="https://www.youtube.com/shorts/ngrJM2NUNz4">Take his Talents to South Beach</a> if things get ugly here.
So, as long as the Oilers are contenders, there&#8217;s no reason to worry.

Remember when Connor McDavid signed his contract?



<a href="https://oilersnation.com/news/connor-mcdavid-officially-signs-eight-year-100-million-contract">It was early July in 2017</a>. The Oilers had just ended a decade-long playoff drought, thanks largely to a Hart and Art Ross Trophy-winning campaign from their 20-year-old captain.

After just two seasons and 127 games in the NHL, Edmonton's front office had no qualms making an eight-year, $100 million commitment to the first-overall pick from the 2015 draft. Already arguably the best player in the league, McDavid would surely lead the Oilers to glory very soon.

In the subsequent years, despite 224 points over 160 games from the young phenom, Edmonton missed the playoffs in both 2017-18 and 2018-19. The team slowly built into a serious contender through the course of <a href="https://oilersnation.com/news/connor-mcdavid-leon-draisaitl-locked-up-for-the-next-eight-years">McDavid's eight-year deal</a>, but, entering the contract's final season in 2025-26, the Oilers still don't have a Stanley Cup.

With the benefit of hindsight, maybe he would have handled his second contract differently. Those lost seasons are likely being considered in the negotiation for contract three.

<a href="https://www.tsn.ca/nhl/connor-mcdavid-says-confidence-in-edmonton-oilers-has-never-been-higher-1.2355239">When McDavid spoke with TSN's Ryan Rishaug on Thursday</a>, he stressed his confidence that the Oilers can win the Stanley Cup this season. Beyond that? Let's just focus on this year.
<blockquote>“My confidence in this team this year has never been higher. That's what I can say about that.

Listen, does anyone have a crystal ball and know what two years, three years, four years, five or whatever (will look like)? Nobody has a crystal ball. Nobody knows what that's going to look like. The belief is not the issue, not that there is an issue. It's just that we're working through it and we're working through it together. I think Jax (Jeff Jackson) said we're trying to find a razor’s edge and part of that’s true. We’re trying to find a scenario that works for everybody in terms of my family, my family’s security, a deal that makes sense for the team to continue to have success.

My belief in this season and the players this year has never been higher.”</blockquote>
After consecutive trips to the Cup Final that resulted in losses to the Panthers, the Oilers again appear poised to come out of the Western Conference. They plowed through the L.A. Kings, Vegas Golden Knights, and Dallas Stars with an impressive 12-4 record before falling in six to Florida.

But that's this year. What about beyond that? How do the Oilers look through the rest of the decade? It's difficult to say how veteran forwards like Zach Hyman and Ryan Nugent-Hopkins will perform in their mid-30s. It's already difficult to say if the team can still lean on 35-year-old Mattias Ekholm to be a top-pairing defenceman. And, of course, there's the <a href="https://oilersnation.com/news/edmonton-oilers-stuart-skinner-new-goalie-coach-goal-play-team-canada-stanley-cup">goaltending situation</a>.

Oilers CEO and McDavid's former agent, Jeff Jackson, went on the radio earlier this week to <a href="https://oilersnation.com/news/edmonton-oilers-ceo-jeff-jackson-discusses-connor-mcdavid-contract">pour water on any smoke</a> that the team's star player is headed for an exit. Jackson added that he and McDavid’s new agent, Judd Moldaver of Wasserman Hockey, had talked for over an hour earlier about potential contract options, reinforcing that his former client is taking his time to weigh multiple options.

All signs seem to point to McDavid signing another contract with Edmonton, but it also seems inevitable that this isn't another eight-year pact. The goal isn't to constantly re-sign for more money alongside a rising salary cap; the goal is not to be stuck on a team that isn't competing for the Stanley Cup.
<blockquote>"I think guys within the Edmonton market understand what my desires are because they know me. The players understand where I'm at," <a href="https://www.tsn.ca/nhl/connor-mcdavid-says-confidence-in-edmonton-oilers-has-never-been-higher-1.2355239">McDavid told Rishaug</a>. "It's not about trying to make the most amount of money. I think my former agent knows that, given how has the last negotiations went.

It's about winning. It's about winning over and over again and that's my priority. All with the understanding that I put a lot into this. It's been 25 years of putting a lot of everything I have into this, and my family deserves that security, they deserve the lifestyle that being a pro hockey player and being very good at it and all the work that goes into it deserves. So, it is trying to find a balance."</blockquote>
None of this reads like McDavid is ready to rush out the door to join his childhood Toronto Maple Leafs on a quest to get beyond the second round of the Stanley Cup Playoffs for the first time since the early years of the George W. Bush administration. It's that he wants the flexibility to <a href="https://www.youtube.com/shorts/ngrJM2NUNz4">Take his Talents to South Beach</a> if things get ugly here.

So, as long as the Oilers are contenders, there's no reason to worry.

Connor McDavid is confident in the Oilers right now; the question is Edmonton’s long-term outlook

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