November 6, 2023 by Eric Friesen

When Edmonton Oilers CEO Jeff Jackson was hired in August, he took over a team with Stanley Cup aspirations. However, through one-quarter of the season, the Oilers find themselves in 30th place in the NHL standings with a dismal 9-12-1 record.

While the Oilers haven’t been off to the start they expected, they have won four straight and are 7-3-0 in their last 10 games. Jackson spoke with TSN’s Gino Reda at the NHL Board of Governors meetings in Seattle on Monday about the team’s early struggles and their outlook for the future.

“I was sort of calm through the whole start of the season,” Jackson told Reda on Monday. “It was a rough start for the team for a few reasons. But the team’s playing much better of late, and we’re getting a lot of production from our best players, and getting some timely goaltending, and I think the big thing is we’re playing really good team defence, which is contributing to the streak we’re on right.”

The pressures of being widely regarded as Stanley Cup favourites coming into the 2023-24 season could have contributed to the Oilers sluggish start. And while the players might be anxious to just get back to the playoffs and make up for how last season ended, they still have to play well enough through 82 games to earn a spot in the tournament.

“Going into the season, I think the expectations for the team were very high, externally and internally,” said Jackson. “[The media picks a team to win the Cup] and sometimes that gets into people’s heads a little bit. I think we’ve come back down to Earth now, and realized that the league is very good, there’s a lot of parity, and every night is a struggle. So, if we can keep this going, I think we’ll dig ourselves out of the hole we put ourselves in.”

Related: Oilers name Jeff Jackson CEO of Hockey Operations

The Oilers have locked up core players like Ryan Nugent-Hopkins, Zach Hyman and Darnell Nurse into the back-half of this decade or later, but re-signing superstars Connor McDavid and Leon Draisaitl long-term is the top priority for the organization. Draisaitl is eligible to sign an eight-year contract extension on July 1, 2024, while McDavid can sign an extension the following summer. Though this is McDavid and Draisaitl’s ninth and 10th seasons with the Oilers, respectively, Jackson believes they still have many years of strong hockey ahead of them.

“I said it in my opening media availability when I got the job, our job is to be there competing for the Cup,” said Jackson. “There’s urgency to it, there’s windows, but [McDavid and Draisaitl] are still young, and there’s a lot of runway for them. It’s not do or die, but we’ve got to be there competing every year. So, that’s part of the equation, just making sure we’re in the mix to win the Cup. It’s really hard to win the Stanley Cup.”

“When Covid hit and every ground to a halt, when managers were putting together teams in 2019-20, they were looking at the cap going up,” said Jackson. “You can sort of predict how predict how much it’s going to go up. And Ken Holland, just like a lot of general managers around the league, was assuming that, and then you get roadblocked. So, we have to get creative to try to find opportunities to create cap space and give ourselves some options. Ken and our pro scouts are working hard every day to do that.”

Despite minimal cap increases since the summer of 2019, General Manager Ken Holland has been able to upgrade his roster, and the Oilers have qualified for the playoffs in each the past four seasons. However, it’s clear that more work needs to be done for this club to reach its ultimate goal.

“I’m not finding [the position] difficult,” said Jackson. “It’s challenging that the start has made it even more so, but I’m coming in with a long-term view. But I’m also looking at that urgency in the short-term for key players, and just trying to do the best job I can every day, and making small steps that will make us better in the long run.”