Matthew Knies remains a live target for Montreal, and Martin St-Louis could still benefit if Kent Hughes revisits a deal that nearly got done.
The Canadiens came very close to landing the Maple Leafs forward at the trade deadline, and the framework was already in place.
According to multiple reports, Hughes and then-Toronto general manager Brad Treliving had agreed to the terms of a trade before the window closed.
Toronto was reportedly set to receive Alexander Zharovsky, Bryce Pickford, and two first-round picks, while Knies was headed to Montreal.
Then everything collapsed at the last second.
Even though both sides had agreed, the paperwork reportedly reached the NHL after the 3 p.m. deadline, and the deal never became official.
The Knies file is back in play
That miss still stings because Knies just put up 66 points, including 23 goals, in 79 games, exactly the kind of power winger Montreal has been trying to add.
For a club still looking to get bigger and harder to handle in the top six, this wasn't a minor swing. It was a major one.
Most people assumed the story was finished once John Chayka arrived as Toronto's new general manager.
Instead, the file has come back to life.
According to chatter around the league, several executives now expect Knies to be moved at some point this offseason, which puts Montreal right back in the conversation.
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"The Maple Leafs are reportedly receiving several calls [regarding Matthew Knies] and their general manager, John Chayka, is said to be receptive." - via TVA Sports
That matters for Hughes because it suggests the Canadiens may get another shot at a player they were already prepared to pay heavily for.
According to Incarcerated Bob, Montreal is still pushing on the Knies front, even with more clubs now circling.
"The Canadiens remain very involved in the Matthew Knies situation with the Leafs.
The new general manager could pose a problem, however. The Rangers, Flyers, and Blackhawks are also teams to watch." - Incarcerated Bob
That changes the pressure around this situation. Montreal is no longer chasing a quiet deadline deal. It may now be entering a bidding fight.
One thing is clear: Hughes hasn't backed off, and the Canadiens remain very much in this race.
Should Kent Hughes still go all-in to acquire Matthew Knies?
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