The expected path for Anders Lee once free agency begins Wednesday is now the official path for the Islanders captain. 

Lee will test the market despite the Islanders improving their offer, according to TSN, and while the Islanders remain an option, he’ll reportedly listen to offers from other teams. If Lee departs, it will mark the end of a 14-year tenure with the Islanders that started in 2009 as a sixth-round draft pick, reached the NHL three years later when he debuted and then took on a deeper meaning when he became captain in 2018.

And if Lee returns, it will signify that he and general manager Mathieu Darche found some way to compromise just before negotiations reached the point of no return with Lee signing elsewhere. 

When asked about the status of Lee and negotiations Friday, Darche said he was still talking with agent Neil Sheehy. “We’ll see what happens in the next three days,” Darche added. The 35-year-old Lee remained an integral piece of the Islanders lineup last season, even if he fell short of 20 goals for the first time in a full season since 2015-16. 

Now that conclusion, at least when it comes to Lee testing the market, has settled into place. It’s a risky one, especially if Lee ends up departing. It serves as a jarring flashback to 2018, months before Lee took on the captaincy, when John Tavares also walked July 1. It would instantly become the primary question the Islanders face in free agency. 

As the 2025-26 season neared its conclusion, Lee said he wanted to finish his career with the only organization he has ever known. His seven-year, $49 million deal that he signed in July 2019 and that will expire at noon Wednesday captured his place as a franchise cornerstone, and the numbers — 308 goals and 549 points across regular-season games — only added to that. 

“It’s where I’ve played my entire career,” Lee said in April. “It’s where I’ve put my best foot forward as much as I can. I don’t take anything for granted.” 

There will be a handful of what-ifs lingering, too, if Lee wears a different sweater next season. Lee — who finished with 19 goals and 42 points in 2025-26 — and the Islanders got back to the Eastern Conference finals six years ago and haven’t won a playoff series since.

He’d finish 77 games short of becoming the fourth player in Islanders history to skate in 1,000 games with the team, something Darche, at the end of the season, said he wanted to see. 

The caveat to Darche’s wish, though: an agreement that worked for both sides needed to exist. Since taking over the Islanders, Darche has also made a difficult decision to deal Noah Dobson to the Canadiens in a trade that, for one season at least, worked out for each team.

The magnitude of Lee leaving would surpass that, though — potentially turning Wednesday into a critical juncture in Islanders history. 

If Lee departs for another deal and a compromise cannot be reached, the Islanders will assemble for the 2026-27 campaign and instantly stare down a major void in their lineup. That would be the most daunting reality check of all.