Three years ago, the Maple Leafs had a window to move Morgan Rielly that may never open that wide again.
According to Jeff Marek, Toronto and San Jose had the makings of a deal that would have sent Rielly to the Sharks for Erik Karlsson, but the talks never crossed the finish line because the Leafs wanted heavy salary retention on Karlsson’s then-$11.5 million contract.
“For a while there I think we all thought there was gonna be something between San Jose and Toronto around Erik Karlsson, and Rielly would've been part of it; retention I believe was a major issue there.”
Karlsson eventually landed in Pittsburgh, with San Jose retaining $1.5 million annually and the Penguins carrying a $10-million cap hit. Marek didn’t say exactly how much Toronto was asking San Jose to keep, but the retention piece was clearly the stumbling block.
At the time, Rielly was 28 and still in his prime. He had just finished a 2022-23 regular season that was uneven by his standards, putting up 39 points in 65 games, then followed it with 12 points in 11 playoff games. That postseason run helped keep his stock strong, and Toronto still saw him as a core piece on the blue line.
The problem for the Leafs is that the value curve has moved the other way since then. Rielly didn’t build on that stretch, and now he’s far tougher to move than he was when Toronto had the chance to act.
There was another possible San Jose angle this season, but the Sharks pursued Darnell Nurse instead.
Toronto has also tried to address the spot around him. Darren Raddysh arrived after a 70-point breakout season, and the club is hoping he can carry that forward. He brings a different package than Rielly - a blazing fast and hard shot, plus a bit more physicality.
That shift matters because Rielly is now arguably the most expendable he has ever been, even if the mechanics of a deal are brutal. He carries a $7.5 million cap hit and a full no-movement clause.
He did submit a four-team list to the Maple Leafs this past summer, though that only reflects preferred destinations if a trade were ever worked out. It does not mean he has to be moved, or that he would necessarily go to one of those teams.
And there’s a bigger trap waiting if Raddysh doesn’t become the star No. 1 defender Toronto needs. Then the Leafs could be staring at the same kind of problem all over again: one big season, then regression, plus trade protection and a pricier contract. At that point, moving the player becomes almost impossible.
In the end, Toronto’s biggest mistake may not have been keeping Rielly three years ago. It may have been believing his production was going to keep climbing.
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