Canadiens and Maple Leafs Could Emerge as Trade Partners

Toronto, meanwhile, sits six points outside of a playoff position. That gap is not insurmountable, but the weeks following the Olympic break will determine everything. If the Leafs stumble, management could pivot toward selling pending unrestricted free agents (UFAs) rather than chasing a wild-card miracle.

Calle Järnkrok, Scott Laughton, Bobby McMann, and Troy Stecher are all pending UFAs. None are franchise-altering players, but all offer something contenders covet in March: depth, experience, and playoff-style versatility. Järnkrok is a reliable two-way forward who can play anywhere in the lineup. Laughton brings grit and leadership. McMann offers secondary scoring. 

Montreal could reasonably look at one or two of those names as short-term additions without sacrificing long-term flexibility. For a team not looking to make a blockbuster splash but rather tighten the margins, this type of move fits perfectly.

Rare Trade Partners

Of course, this is easier said than done. The Canadiens and Maple Leafs are historic rivals. These teams don’t exactly pick up the phone casually. Since 2000, they have completed just three trades.

In 2003, the Maple Leafs acquired Doug Gilmour from Montreal for a sixth-round pick, a depth move for a playoff run. In 2008, Toronto acquired Mikhail Grabovsky for Greg Pateryn and a second-round pick. Then in 2018, the Canadiens sent Tomas Plekanec and Kyle Baun to Toronto in exchange for Kerby Reichel, Rinat Valiev, and a second-round pick.

That’s it – three trades in over two decades. The scarcity isn’t accidental. Rivalries amplify every move. No general manager wants to be the executive who gifted a rival a playoff difference-maker. 

But here’s the key: none of the potential names on Toronto’s UFA list represent long-term franchise-altering risks. If the Maple Leafs are selling, they’re selling expiring assets. If Montreal is buying, they’re buying short-term help. That dynamic lowers the political temperature considerably.

Rivals That Could Help Each Other

The idea of Montreal and Toronto helping each other might feel uncomfortable to fans, but from a business standpoint, it can make sense. If Toronto falls further out of the race, recouping mid-round picks or a depth prospect for players who might walk in July is logical asset management. A third-round pick or a young B-level prospect from Montreal could be more valuable than keeping a pending UFA through a lost spring.

For the Canadiens, acquiring a veteran depth piece without surrendering premium assets aligns with their competitive window. Montreal is not in win-now-at-all-costs mode. But they are in the playoff race and still want to win. Adding playoff-tested depth for a reasonable price is exactly the type of move that strengthens a young core without disrupting it.

At the end of the day, trades are about value alignment. If Toronto decides to sell and Montreal sees an opportunity to add depth at the right price, history shouldn’t be an obstacle. It won’t be a blockbuster. It won’t redefine the rivalry. But it could be one of those quiet deadline deals that looks minor in March and feels significant in May.

Rivals don’t often cooperate. But sometimes, in the right circumstances, both sides can walk away better. And if that happens between the Canadiens and Maple Leafs? That would be a deadline storyline nobody saw coming.