For the first time in a long time, this offseason feels like there is a legitimate reason to believe blockbuster traders are coming. Since the Stanley Cup was awarded, teams have started making deals, with at least four trades already completed, and a couple of bigger names have been moved.
The biggest is the Brady Tkachuk-to-Florida deal that went down late Sunday night.
Next summer offers one of the most staggering collections of pending free agent situations the NHL has ever seen. Some contracts will expire at the end of the 2026-27 season. Others one year later, but trade conversations will begin, ensuring that the team that feels a trade has to be made maximizes any potential return.
Sure, we’re waiting on Dylan Larkin or Darnell Nurse news this offseason. To show how much bigger next season could be, let’s go through each name and where things stand heading into what could be a historic 2026-27 offseason:
Connor McDavid
Easily the biggest name everyone will be talking about is Connor McDavid. The captain of the Edmonton Oilers signed a two-year, $25 million extension at $12.5 million AAV — the same rate as his previous deal — which runs through the 2027-28 season and makes him a UFA after that. Going short-term was a deliberate choice. He gave the Oilers a very specific window — a couple of extra years to make a final run at the Stanley Cup, and then essentially a year of control that makes him an enormously valuable trade asset if things go sideways. So far, it’s not looking great.
There are some, like Oilers color analyst and insider Bob Stauffer, who are predicting McDavid’s next contract will be a seven-year extension in Edmonton. Others aren’t sure he’ll give the Oilers more than this season to turn the ship around.
Edmonton and McDavid are so desperate to win, they appear to be hiring Mike Babcock as their next head coach. If it doesn’t work, why would McDavid want to stay? Should the Oilers get the feeling he’s leaning more toward leaving than sticking around, trade chatter will consume the 2027 offseason rumor mill.
Auston Matthews
Much like McDavid, Auston Matthews has two years remaining on his contract. He’s making $13.25 million per season and becomes a UFA in July 2028. He has a full no-movement clause in both remaining years, but he might be willing to work with the Leafs if the 2026-27 season goes anything like the 2025-26 season did.
The Maple Leafs missed the playoffs, Matthews got hurt, and the organization went through a full front office overhaul — Chris Johnston reported a few weeks back that Matthews isn’t even sure if he’ll be back in Toronto next season, telling league sources he wants to see the roster “meaningfully upgraded” before committing. The latest reports are more optimistic: new GM John Chayka visited Matthews and called him “a happy captain who wants to win in Toronto,” and Pierre LeBrun reported Matthews is “most likely staying put” for at least another season.
But things can change quickly. If Toronto’s changes don’t produce better results, Matthews could hit the market, and there will be no shortage of teams showing interest.
