Ken Holland appears scared to make a big trade to better the Edmonton Oilers and that’s a problem

For arguably the first time since the Edmonton Oilers made their run to the cup finals, the team is in the trade market for big-name players.

We’ve heard the Oilers linked to defencemen Jakob Chychrun, and Erik Karlsson, and superstar forward Patrick “showtime” Kane. There are legitimate arguments for the Oilers going after and acquiring any one of these, even though navigating tricky cap constraints would follow.

After all, the players deserve this kind of move. Connor McDavid and Leon Draisaitl nearly single-handedly carried the Oilers to the Western Conference Finals last year and they’ve reportedly been pushing for the team to add a puck-mover. How important do the Oilers feel this need is? So much so that they’ve reportedly made it a “key acquisition” for the club.

So what’s the hold up? Well, one issue is the aforementioned cap constraints. They need to be dollar-in, and dollar-out for any trade they make. That’s an issue, for sure, but it’s not holding back other teams. Minnesota, for example, has already retained salary on two big trades. They ate money on Ryan O’Reilly, who went from St. Louis to Toronto, as well as on Dmitri Orlov, who went from Washington to Boston. Beyond Kane, Chychrun and Karlsson both have term, so that could complicate some things. Not an immovable object, however.

But there seems to be another big blockade for the club: general manager Ken Holland.

It was just last week when we heard Bob Stauffer tee off on the Oilers during their broadcast against the Flyers.

“Sometimes you just get a feel. My feel is [the players are] waiting for something to happen here… I’m around these guys, both home and away… and I’m here to tell you I can sense it, I can feel it,” Stauffer said. “The impetus is Ken Holland is well compensated. That management team is privileged to have the roles they have, and there should be some traction. I don’t want to be the guy who overpromises and underdelivers, but the time is now.”

Now? It’s Ken Holland’s own son, Brad, whose comments are painting a clear picture of how things are in the Oilers’ trade war room these days. He spoke with The Athletic’s Daniel Nugent-Bowman recently about his role as assistant general manager and director of pro scouting, and how the Oilers are looking to approach things.

And in Brad’s eyes, there’s some tepidity from his father on how to approach the deadline.

“You’re looking to add the best piece you can,” Brad said. “If there’s a big name out there — I’ll be honest — my gut is (to go for) the big move. That’s what I like. But that’s been tempered a little bit by Ken because he’s seen it go south before.

“I said to him one time, ‘Fortune favours the bold.’ He kind of laughed at me. He said, ‘Maybe you can be bold when you have the chair.”

To be quite honest, these quotes are jarring to hear.

We’re in year eight of Connor McDavid. Year seven of Leon Draisaitl. They just made the conference finals last year, and now we’re talking about the Oilers GM not wanting to take a big swing to better the team because he’s “seen it go south before?”

Let’s be crystal clear here: guys like Chychrun, Karlsson or Kane are not Andreas Athanasiou. They’re not even close, to be fair. We’re talking about guys who have established NHL players who are playing at a very high level, not bottom-six player who was looked at as a redemption project of sorts.

It’s a borderline fireable offence for the Oilers to sit on their hands here. They need to be all-in this year, and over the next number of years. Over the years they’ve accumulated a largely solid supporting cast of players, but that should never end when you’re in your window like the Oilers are.

The time is now, Ken.