Matthew Knies was close to joining Martin St. Louis in Montreal, however late paperwork from Toronto killed a deadline blockbuster.
The part that Elliotte Friedman forced into the spotlight is that. Friedman stated on 32 Thoughts that the Leafs-Canadiens agreement fell through because it was filed at 3:01 ET, which was one minute after the hard stop.
This story’s impact is altered by that. This trade did not break down due to a player, a selection, or a last-minute change of heart. It died on time.
The framework is what is surprising. Prior to the 2026 deadline, Matthew Knies was almost transferred from Toronto to Montreal, according to Friedman.
For such a boisterous rivalry, that is a huge swing. One of the Leafs’ most daring choices in years would have been to move a promising power winger to the Canadiens, which would have put a significant player right into Martin St. Louis’s top six.
When you contrast the miss with Toronto’s season, it appears much more awful. Since the Maple Leafs ended the season with 78 points (32-36-14) and did not make the playoffs, every deadline decision is now being reconsidered.
” Elliotte Friedman: Regarding the Leafs/Canadiens Knies blockbuster: I heard it didn’t happen because it was submitted at 3:01 [ET] – 32 Thoughts (6/5) ”
Montreal went in the opposite direction. The Canadiens reached 106 points, finished 48-24-10, and advanced to the Eastern Conference Final.
Fans are shocked by Elliotte Friedman’s recent revelation regarding the unsuccessful trade between the Leafs and the Canadiens.
Since the Leafs’ front office is already undergoing a reset, there is no need to make any more changes. The organization is attempting to promote a new direction after dismissing both Craig Berube and Brad Treliving this spring, with John Chayka now in charge of hockey operations.
This makes missing the deadline seem more like a clerical mistake than a major problem. It strikes at the execution, which is the one thing a team in flux cannot afford to be sloppy about.
There is also the Knies angle itself. Players like that are not easy to replace, and rival teams do not usually get offered that kind of age, size, and wing value unless the stakes are real. That tells you Toronto believed it was making a serious hockey trade, not just kicking tires.
For Montreal, this is the kind of near-hit that only fuels the what-if talk. St. Louis already had a club on the rise, and adding Knies to that forward group would have changed the feel of the room right away.
For Toronto, it is harsher. The Leafs did not only miss on a blockbuster. They missed it by 60 seconds.
And in a market that chews on every front-office move, that is the kind of detail that does not go away fast.
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