3 Potential Destinations for Jason Robertson at 2027 Trade Deadline – The Hockey Writers – Trade Deadline

Jason Robertson had his name tossed around in trade speculation for months before he finally signed a new one-year deal with the Dallas Stars. Following a long negotiation, the two sides were able to avoid arbitration and come to an agreement at $12 million, lower than what many fans expected.

The main issue with this deal is that Robertson is an unrestricted free agent (UFA) following the conclusion of the 2026-27 season, giving him the chance to walk to free agency, where the Stars would lose him for nothing.

With that in mind, it seems like there is a reality where the Stars could look to trade Robertson at the 2027 Trade Deadline, rather than lose him for nothing, if the two sides aren’t close on a new long-term agreement by that point.

The Seattle Kraken almost acquired Robertson, and in exchange, they were rumoured to be willing to part with a huge trade package that included their first-round draft pick. If Robertson has another strong campaign, the Stars could get even more out of a deal with a contending team.

Some fans believe Robertson took a one-year deal to do the Stars a favour and wait until they clear some cap space before giving him a raise, but I don’t think that’s the case whatsoever.

If the Stars and Robertson haven’t signed a new extension by the trade deadline this season, there is a world in which they could trade him, and these are three potential destinations he could land at in that case scenario.

Boston Bruins

Any team that acquires Robertson would likely want him to sign an extension, especially if they’re going to be giving up a lot of future assets and depleting their prospect pool and draft capital.

The Boston Bruins are an interesting fit for Robertson. They added JJ Peterka to bolster their top-six forward group and have a solid future ahead of them with James Hagens added to the mix, but they still need to add some offensive firepower before they can be considered championship contenders.

The Bruins have the assets to make a deal for Robertson at the deadline, but they need to prove themselves as an attractive destination for Robertson to want to extend.

Robertson likely only ends up with the Bruins if they have a strong start to their 2026-27 campaign and are in a playoff spot come the deadline, but it’s a good fit.

Edmonton Oilers

The Edmonton Oilers had close to a perfect offseason. They added goaltending depth, fixed their defensive depth, and replaced Kris Knoblauch. The one thing that fans hoped they would do is add another top-six forward, but they didn’t do that.

However, they have put themselves in a strong position to be buyers at the 2027 Trade Deadline. They will have enough cap space to make a huge acquisition, which could include a top-six forward, and Robertson seems like a perfect fit.

This approach allows the Oilers to give Isaac Howard a look in a bigger role this season before deciding on what they need to add. If he fails, they can add Howard to a trade package for a top-six forward. If he succeeds, they can keep him around and add even more firepower utilizing draft capital and other prospects.

The idea of playing with Connor McDavid, Leon Draisaitl, and Evan Bouchard is attractive on its own for Robertson, and considering the Oilers are going to be Stanley Cup contenders for the next few seasons at minimum, he would likely be open to extending long-term with them, and the Oilers have the cap space to give him whatever he wants.

Pittsburgh Penguins

The Pittsburgh Penguins were linked to Robertson for months and considered the frontrunners to land him if he were to be traded, and they still remain a good fit.

The problem is that the Penguins might not be in contention come the 2027 Trade Deadline. It’s hard to ever bet against Sidney Crosby, but the rest of the Penguins team doesn’t give confidence that they will be legitimate contenders this season.

In the rare case that they are in a playoff spot, the Penguins seem like the best fit for Robertson. They have the assets to make a deal work, and with a bright future ahead of them, Robertson could see the Penguins as a logical long-term destination, essentially being the new star of the team when Crosby hangs up his skates.

It’s hard to imagine Robertson playing anywhere but with the Stars, but if the two sides can’t find common ground on a new deal before next summer, it isn’t out of the realm of possibility that he gets traded at the deadline.

As the 2026-27 season approaches, be sure to continue following The Hockey Writers as your source for news, updates, and more from around the NHL and the hockey world.