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Could Jason Robertson End Up A Red Wing?

Originally posted on Inside The Rink
By Alexander DeBerardinis | Last updated Jan 21, 2026 2:44 PM ET

And we’re back. A couple of months ago, I did one of my Deal or No Deals for Detroit, and the headliner at the time was Jason Robertson. After weeks of trade-related pieces, Jason Robertson is yet again back on the writer’s block for the Red Wings. According to Nick Kypreos on the Real Kyper and Bourne, if Jason Robertson asks for more than twelve million, Dallas may look to trade him.

Yeah right. Jason Robertson is not going to be asking for less than twelve. He may settle for less in Dallas, but he certainly won’t want to. Dallas is going to have sixteen million in cap this offseason. Believe me, the cap is fake, especially in no-tax states. But this one might be a little hard to weasel out of. So, for the second year in a row, does it make sense for Detroit to sell the farm on Robertson?

Still yes, but let’s go deeper.

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Why Robertson Fits in Detroit (Again):

Well, at least this is still in my repertoire. Let’s start with what Red Wings fans care about: why Robertson helps the team.

Robertson plays left wing and can do it at the highest level. For yet another year, he takes on mostly defensive deployments and against top-six competition on the other team. He would be the first player since Alex DeBrincat’s brief stints that actually deserves to play top line left wing. Robertson’s 6’3″ frame would also make him a big body in the top six, something they severely lack with DeBrincat, Raymond and Kane right now.

Beyond that, Robertson fixes the number one problem with the Red Wings’ future outlook. There is no superstar coming to Detroit, Sandin-Pellikka isn’t a world-beater, at least not yet, and the rest of the cast looks good but not game-breaking. Detroit has all the pieces in the world to surround an elite player well and turn the team into a cup contender, but they don’t have a clear way to get that elite player. Robertson cures that.

For Robertson, he gets a lot of what he wants. First of all, Detroit has over double the amount of cap space Dallas has, and I don’t think Detroit will be shy about spending on Robertson. It wouldn’t surprise me if Detroit has no issue making Robertson the second-highest-paid player at fifteen million dollars. Now, the no-tax state will have something to do with that, but Detroit is a huge hockey market and has more advertising opportunities. Not to mention, housing costs are cheaper. He would also be side-by-side with his brother Nick Robertson in Toronto, if the Hughes saga taught us anything, that matters.

Now, for Dallas, I do think there is some layover. Detroit has a million prospects, admittedly none at right defence where Dallas would want, but plenty to fill out the roster nonetheless. While I’m sure Dallas doesn’t want futures, guys like Kasper, Danielson, Finnie, or MBN can be valuable now. Detroit coughing up first round picks isn’t nothing either. Dallas can just flip the picks if they can find other trade partners.

When Might We See a Deal?

The offseason is the short answer. I don’t know why, in good conscience, Dallas would move Robertson amidst a cup run. Detroit could offer anyone on the roster, and I don’t think they would have the impact Robertson would have. The truth is, Dallas is going to wear down Robertson and make sure there is no chance they can keep him before they consider a move. That’s not going to be a conversation they can have well during the season. Maybe his Olympic snub helps there, who knows.

But Detroit is going to need to come out of the offseason as the leader of a bidding war. Other teams that are in on him, like Toronto or Montreal, would likely be offering a similar return of picks and prospects for him; you just have to hope you can outbid them then if it gets to that point.

Mock Trade:

Dallas Stars Receive: Emmitt Finnie, Mason Appleton (75% retained), Carter Mazur, Anton Johansson, 2026 1st round pick, 2027 1st round pick, 2028 3rd round pick, 2028 6th round pick

Detroit Red Wings Receive: Jason Robertson

Sticker shock? Personally no. I actually still think this is pretty cheap. I think how quickly I would accept this tells me that it’s still probably not enough. My idea here is that Dallas has a pretty shallow left side, so Finnie can come in and give good energy there. Mason Appleton will give any team good minutes in the bottom six. Anton Johansson looks promising and is Detroit’s only promising right-handed defence prospect. Mazur also gives them a prospect option.

The picks are pretty obvious; they’re ammo for Dallas to make moves. They can grab another good player in the offseason with that kind of draft capital. I think those two picks could have been parts of an Andersson deal or a Sherwood deal this season, for example.

Don’t count out Jim Nill to pull some strings. Robertson is still a monster and certainly not one he wants to lose.