The past few seasons have been some of the best for the <a href="https://www.dailyfaceoff.com/teams/edmonton-oilers/line-combinations">Edmonton Oilers</a> in recent history, but they&#8217;ve still fallen short of the ultimate goal of lifting the Stanley Cup.

This week, <a href="https://www.dailyfaceoff.com/news/former-nhl-montreal-canadiens-st-louis-blues-new-york-rangers-jaroslav-halak-retires-boston-bruins">Daily Faceoff&#8217;s Matt Larkin</a> has been evaluating the Stanley Cup windows of teams across the league by division, and on Friday, he arrived at the Pacific. At the top of the list in his &#8220;win-now window&#8221; are the Edmonton Oilers. Coming off back-to-back Stanley Cup Final finishes where they failed to get the job done, it&#8217;s not hard to see why.
Here&#8217;s some of what Larkin had to say about the team:
<blockquote>Stakes don’t get any higher than, “We’ve lost in the Stanley Cup Final two consecutive seasons and this generation’s greatest player is in the final year of his contract.”
The Oilers are about as all-in as a team can be. The Oil have $37 million tied up in Connor McDavid, Leon Draisaitl and Evan Bouchard for this season, a number that will climb once McDavid re-signs (sorry to burst the bubble of 31 fan bases, but I still expect him to).
They had to say goodbye to a number of support pieces from the team that made the 2024-25 Final: Viktor Arvidsson, Evander Kane, Corey Perry, Connor Brown, John Klingberg, Jeff Skinner. It becomes harder to compete each year when a few players (justifiably) consume so much of your cap space. That’s why it stings that Edmonton couldn’t finish the job the past two Finals.
Next summer, we could see $16 million or more of McDavid’s next deal added to the books, while defensemen Mattias Ekholm, Jake Walman and Brett Kulak and goaltenders <a href="https://oilersnation.com/news/ask-dubey-changing-goalie-coaches-extension-stuart-skinner-edmonton-oilers">Stuart Skinner and Calvin Pickard</a> are set to become UFAs, so the team could look very different. It’s safe to say 2026-27 carries an air of urgency.</blockquote>
Joining Edmonton in Larkin&#8217;s &#8220;win-now window&#8221; from the Pacific Division are the Los Angeles Kings and the Vegas Golden Knights. The Kings are beginning to get bogged down by bigger contracts, while the Golden Knights roster is beginning to show its age, leaving both teams with a desire to go all in before it&#8217;s too late.
Meanwhile, the <a href="https://oilersnation.com/news/lukas-dostal-new-contract-edmonton-oilers-stuart-skinner-next-contract-comparison">Anaheim Ducks</a> and Calgary Flames were placed in the category of &#8220;window opening,&#8221; the San Jose Sharks were labelled &#8220;window under construction,&#8221; while the Seattle Kraken and Vancouver Canucks received the unfortunate designation of &#8220;window smashed.&#8221;
All things considered, Edmonton&#8217;s in a good place right now, especially when you consider the state of the team just one decade ago. But it&#8217;s clear that with McDavid set to hit free agency and a relatively shallow prospect pool, the time is now for the Oilers to get the job done.
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Edmonton Oilers Vancouver Canucks Leon Draisaitl Conor Garland

The past few seasons have been some of the best for the <a href="https://www.dailyfaceoff.com/teams/edmonton-oilers/line-combinations">Edmonton Oilers</a> in recent history, but they've still fallen short of the ultimate goal of lifting the Stanley Cup.



This week, <a href="https://www.dailyfaceoff.com/news/former-nhl-montreal-canadiens-st-louis-blues-new-york-rangers-jaroslav-halak-retires-boston-bruins">Daily Faceoff's Matt Larkin</a> has been evaluating the Stanley Cup windows of teams across the league by division, and on Friday, he arrived at the Pacific. At the top of the list in his "win-now window" are the Edmonton Oilers. Coming off back-to-back Stanley Cup Final finishes where they failed to get the job done, it's not hard to see why.

Here's some of what Larkin had to say about the team:
<blockquote>Stakes don’t get any higher than, “We’ve lost in the Stanley Cup Final two consecutive seasons and this generation’s greatest player is in the final year of his contract.”

The Oilers are about as all-in as a team can be. The Oil have $37 million tied up in Connor McDavid, Leon Draisaitl and Evan Bouchard for this season, a number that will climb once McDavid re-signs (sorry to burst the bubble of 31 fan bases, but I still expect him to).

They had to say goodbye to a number of support pieces from the team that made the 2024-25 Final: Viktor Arvidsson, Evander Kane, Corey Perry, Connor Brown, John Klingberg, Jeff Skinner. It becomes harder to compete each year when a few players (justifiably) consume so much of your cap space. That’s why it stings that Edmonton couldn’t finish the job the past two Finals.

Next summer, we could see $16 million or more of McDavid’s next deal added to the books, while defensemen Mattias Ekholm, Jake Walman and Brett Kulak and goaltenders <a href="https://oilersnation.com/news/ask-dubey-changing-goalie-coaches-extension-stuart-skinner-edmonton-oilers">Stuart Skinner and Calvin Pickard</a> are set to become UFAs, so the team could look very different. It’s safe to say 2026-27 carries an air of urgency.</blockquote>
Joining Edmonton in Larkin's "win-now window" from the Pacific Division are the Los Angeles Kings and the Vegas Golden Knights. The Kings are beginning to get bogged down by bigger contracts, while the Golden Knights roster is beginning to show its age, leaving both teams with a desire to go all in before it's too late.

Meanwhile, the <a href="https://oilersnation.com/news/lukas-dostal-new-contract-edmonton-oilers-stuart-skinner-next-contract-comparison">Anaheim Ducks</a> and Calgary Flames were placed in the category of "window opening," the San Jose Sharks were labelled "window under construction," while the Seattle Kraken and Vancouver Canucks received the unfortunate designation of "window smashed."

All things considered, Edmonton's in a good place right now, especially when you consider the state of the team just one decade ago. But it's clear that with McDavid set to hit free agency and a relatively shallow prospect pool, the time is now for the Oilers to get the job done.

<hr />

<h2>PRESENTED BY 6IX INNING STRETCH PODCAST</h2>
<a href="https://www.youtube.com/@bluejaysnationdotcom"><img class="alignnone size-full wp-image-125977" src="https://publish.theleafsnation.com/wp-content/uploads/sites/4/2099/08/6IS-107-GRA_ShowPromo_727x404-V3-1.png" alt="" width="727" height="404" /></a>

Love baseball? Don’t miss The 6ix Inning Stretch — the brand new podcast from The Nation Network, presented by Betway. Hosted by Toronto sports reporter Lindsay Dunn and 3-time MLB All-Star Whit Merrifield, this weekly show delivers insider stories, unfiltered Jays talk, player interviews, and expert analysis from around the majors. New episodes drop every Wednesday — listen on your favourite podcast platform or watch on the <a href="https://www.youtube.com/@bluejaysnationdotcom" target="_blank" rel="noopener" data-saferedirecturl="https://www.google.com/url?q=https://www.youtube.com/@bluejaysnationdotcom&amp;source=gmail&amp;ust=1752172443559000&amp;usg=AOvVaw1sOwPMZnJZrh2vAplXU6lf">Bluejaysnation YouTube channel.</a>

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