Matthew Knies was 60 seconds from a Canadiens trade, and the Maple Leafs may never get that deal back

Matthew Knies was reportedly one minute away from becoming a Montreal Canadiens player.

Sportsnet’s Elliotte Friedman said on Friday’s edition of “32 Thoughts: The Podcast” that a trade involving the Toronto Maple Leafs winger and the Canadiens missed the NHL trade deadline by 60 seconds. The deal did not fall apart over value. It reportedly died because it was submitted after the 3 p.m. ET cutoff.

Matthew Knies reportedly was part of a major Maple Leafs-Canadiens deadline package

Friedman backed up David Pagnotta’s Thursday report from The Fourth Period that the Canadiens had discussed a package for Knies.

According to Sportsnet, the deal would have sent Knies to Montreal for top prospect Alexander Zharovsky, another prospect and two first-round picks. Pagnotta reported that the second top prospect was not Michael Hage or David Reinbacher.

Friedman said the framework matched what he had heard. “I think the deal involved Knies,” Friedman said on “32 Thoughts: The Podcast.” “As I heard it, it was something similar to that.”

“What I heard is the reason it didn’t happen was it was submitted at 3:01,” Friedman said. That is the kind of miss that does not need much dressing up. The deadline was 3 p.m. ET. The reported submission came at 3:01. If true, the Maple Leafs did not just keep Knies because they changed their mind. They kept him because the clock beat the paperwork.

Sportsnet also noted that Friedman had heard different versions of why the deal was late.

“Now, I’ve heard some different variations on why it was late and whose fault it was that it was late, but I don’t know for sure,” Friedman said. “But suffice it to say, a lot of people pointed fingers at other people or gave different reasons as to why it didn’t happen.”

Why the missed deadline matters more after Toronto’s front-office change

The timing is crucial because Toronto no longer operates under the same setup. The reported trade came when Brad Treliving was still the Maple Leafs’ general manager. Treliving was fired March 30, and John Chayka is now running the front office. That shift changes the entire context around Knies.

Friedman said Montreal could still have interest, but he does not expect the same deal to return. “I think it’s possible Montreal wanted to revisit it, but I don’t believe it will happen,” Friedman said. “I think that deal is off the table now.”

That is the real sting for Toronto. A package of two first-round picks, Zharovsky, and another prospect is not a casual offer. It was the kind of return that suggested Montreal viewed Knies as a long-term piece, even inside one of hockey’s fiercest rivalries.

For the Maple Leafs, the question now is whether missing that deadline saved them from a brutal mistake or cost them a rare chance to restock around Auston Matthews.

Knies still gives Toronto size, scoring, and age. The reported Canadiens package gave them futures, flexibility, and a reset button. The deadline made the decision for them. That may be the only reason Knies never became a Canadien.