Report: Ken Holland will not return to Oilers, may look for new challenge or retire

UPDATE: Late Wednesday night, Sportsnet’s Elliotte Friedman also reported the Oilers were expected to move on from Ken Holland, and that the team may go without a general manager in the short term.

ORIGINAL: Well, folks, it looks like Ken Holland won’t be back with the Edmonton Oilers after all. Despite some smoke yesterday about him sticking around as an advisor if he wanted, Darren Dreger from TSN is now reporting that Holland will leave the organization at the end of his contract, which is set to expire on June 30th.

“We know that as part of the exit interviews, Ken Holland did have a conversation with Jeff Jackson. Our understanding is that Ken Holland will not be back with the Oilers,” said Dreger on the TSN Insiders panel. “His contract expires (on June 30th), perhaps he wants to move on to new challenges or into retirement. Either way, that’s his option, and I expect that Jeff Jackson will discuss this with the assembled media here in Vegas.”

Holland’s run with the Oilers has been a wild ride filled with ups and downs. Brought over from an advisory role with the Red Wings when Yzerman took over as GM, he spent five years trying to turn this ship around after Peter Chiarelli left the franchise in a very weird spot. And while we certainly saw some genuine progress, the ultimate goal—a Stanley Cup—remains a dream after the boys lost to the Florida Panthers in Game 7 in the finals.

As much as this last run was an absolute blast to watch and participate in, the pressure to deliver results was massive, with superstars like Connor McDavid and Leon Draisaitl in the lineup. Unfortunately, Holland will now leave the organization one win away from achieving what he was brought in to do. Close, but no cigar.

While there’s no doubt the man has a resume that would make any GM jealous, thanks to his success with the Red Wings, the bad news is that the Oilers were never able to match what happened all those years ago in Detroit. In Edmonton, Holland made some solid moves, picking up key players like Mattias Ekholm, Zach Hyman, and Adam Henrique, but those were sometimes overshadowed by the deals that didn’t go quite as well.

There are a handful of deals on the Oilers’ books that made improvements incredibly difficult. Giving Darnell Nurse $9.25 million/season after ripping up the Canadian Division during the COVID year certainly comes to mind. So does Jack Campbell’s five-year, $25 million contract, which saw him play only 41 games over the first two seasons before he was relegated to AHL duty with the Condors. I don’t want to pile on these guys here, but you get the point.

The Oilers made the playoffs throughout Holland’s tenure and showed flashes of brilliance — they came within a single win of hockey’s ultimate prize — but consistency was always the issue, and many Oilers fans point to the holes that Old Dutch left open in the roster. Even though it’s hard to criticize a team that was probably two goals away from winning the Stanley Cup, I can’t help but wonder if our fortunes might have been different with a bolder GM at the helm.

It’s always the what ifs that bother you after losing the way the Oilers did, you know?

Either way, Holland leaves the Oilers organization with a 220-121-32 record and nine playoff rounds over the last three seasons. Unfortunately, all three of those seasons ended with our boys losing to the eventual Stanley Cup champion, and I’d be lying if I said that didn’t sting a whole lot. But what’s done is done, and now we look ahead to the next era of Edmonton Oilers hockey.

With Holland stepping away, the Oilers have a big decision to make. They need a new GM who can build on the foundation Holland laid down and finally get this team over the hump and into the winner’s circle. While it’s assumed Jeff Jackson will take over the GM duties on an interim basis at least, the next General Manager will have a lot on their plate in what is a pivotal moment in franchise history.

Not only are there high expectations from fans starving for a Cup win, but there are also some very important contracts that need to be signed very soon. Leon Draisaitl will soon be up for renewal, as will Connor McDavid and Evan Bouchard, and locking those guys down will be a massive challenge. Whoever Jeff Jackson decides on as the next GM, there’s little doubt that the job will come with plenty of pressure from inside and outside of the organization. Who will it be? We’ll have to wait and see.