Is the clock ticking on the Edmonton Oilers Stanley Cup window?

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Is the clock ticking?

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As much reason as there is to be optimistic about where the Edmonton Oilers are trending, and there is plenty given the strides they’ve made over the last two seasons, Stanley Cup windows don’t stay open forever.

There is always an expiration date and for an Oilers team that has finally positioned itself to be a contender every year, that date could be a good eight years away.

Or it could be two.

Maybe even one.

With Leon Draisaitl’s contact set to expire at the end of the 2024-25 season, and a decision on his future needing to be made before the trade deadline in the second year, the Oilers might only have one more opportunity to show that Edmonton is indeed the place to spend the rest of his prime.

They’re on track. Putting together back-to-back 100-plus point seasons and winning three playoff series in two years is exactly what Draisaitl and Connor McDavid need to see. Listening to their end-of-season exit interviews tells you they like what’s happening and believe in the Oilers’ direction.

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That’s why next year is so crucial. Edmonton can’t afford to let the momentum they’ve worked so hard for slip away.

It’s vital that they shore up their remaining holes, make another run and ensure that the two guys holding that window open are around for another eight years.

“It’s very important,” said general manager Ken Holland, who has emptied the tank in the last two trade deadlines to get the Oilers to this point.

“I traded two first-round picks at the deadline for Mattias Ekholm, I traded a second last year for Brett Kulak. I’ve traded lots and lots of picks. I signed Evander Kane to a four-year deal. These are players who have impacted.

“I’m trying. We’re trying. We’re banging away, we’re pushing. But other teams are also trying. It’s why it’s the Stanley Cup. It’s hard.”

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That’s why this playoff exit stings so much. And why nobody even wants to think about what kind of ripple effect a similar exit next spring might have.

“Our guys came out here, they’re devastated, they’re devastated,” said Holland. “I’m devastated, the fan base is devastated. Why are we devastated? Because we went 14-0-1 heading into the playoffs. The second-best record in the NHL behind Boston since the first of January.

“But Boston is devastated. Teams that are out are devastated. We’re devastated. I’ve got guys in there telling me they’re going to the gym next week. They’re not going on vacation. They’re going to work.”

The Oilers’ core speaks glowingly of the team and the city and wanting to finish what they started here. And to a man the whole group believes it is knocking on the door. There aren’t a lot of greener pastures out there right now. That bodes well for Edmonton.

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But there are no certainties in life and in hockey. Nobody knows that more than a GM who’s been around the game his whole life.

“There are no guarantees and givens and entitlements because of this and because of that,” said Holland. “It’s earned. It’s sacrificed. It’s sticking to what you believe. That’s how you become the last team standing.

“We have some great players, those great players we have are digging in. I want you to know that I’m digging in. I want you to know our coaching staff is digging in. Every one of my players is digging in.

“But there are 31 organizations digging in. That’s why, when you win the Stanley Cup, boy do you party. Because it’s not a one-year quest, it’s a lifetime quest. You can’t party enough when you win that thing. It’s a party machine. It’s so hard to get your hands on.”

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And, as the Oilers are learning now, the ironic part of it all is the road to glory involves more failure than success. All Stanley Cup championship teams have lost out in the playoffs far more often than they’ve won it all.

“That’s the league, you have to stick with it,” said Holland. “Detroit couldn’t win the cup in ’94, ’95 and ’96 and the same group of players won the Cup in ’97 and ’98. In 2006, we lost to Edmonton in the first round and won the Cup in ’08.

“I didn’t build a new team. I didn’t get 20 different players. It’s the same players just doing some things differently. I believe in this team we have in there.

“Most of the players in that locker room are in the prime of their career, it’s not like we’re going away. I believe the time is now.”

At long last, “wait until next year” isn’t just a weak and empty slogan after another failed season in Edmonton. This time there is some real substance and promise to what the future holds.

“I want our fans to know that we’re trying,” said Holland. “We’re going to get up off the mat, we’re going to get back at it in September and try to put ourselves back in the same position we were in the playoffs, feeling good and believing. We’re going to try again.”

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