Every so often, an NHL trade comes along that completely rewrites the narrative for a franchise—one that fans and analysts will talk about for years to come.

The Montreal Canadiens, a team with a storied history and countless memorable moments, may have just witnessed one of the most remarkable trade sequences in their existence.

On the surface, it all started with a simple transaction involving the Calgary Flames, but what unfolded next was a masterclass in asset management by general manager Kent Hughes.

Behind closed doors, a series of bold moves and shrewd negotiations quietly set the stage for what could be remembered as the best trade tree in Canadiens history.

Each step seemed ordinary at first, but as the pieces came together, the magnitude of the deal grew exponentially—culminating in the acquisition of top-tier talent and future assets that could transform the franchise for years to come.

What exactly did Kent Hughes pull off? How did a trade that began with “future considerations” end up netting the Canadiens a potential cornerstone defenseman and multiple high-value picks?

The answer is a fascinating journey through the intricacies of NHL trades—a story that’s far from over, and one you’ll want to see unfold in full detail.

Canadiens and Kings logos

Photo credit: HabsFanatics/ NHL

Let’s revisit an incredible trade pulled off by Montreal Canadiens general manager Kent Hughes.

I don’t want to get too carried away, but it’s hard to find a better trade in the history of the Montreal Canadiens.

We’re talking about a trade initially made between the Habs and the Kings to simplify things, but in reality, it all started with a trade between the Habs and the Calgary Flames-one that led to two incredible trades for Kent Hughes (one with Los Angeles and one with the New York Islanders).

Let’s break it down.

The Best Trade in Montreal Canadiens History?

The initial trade is already impressive, but what Kent Hughes did afterward makes that first deal even more unbelievable.

Here’s what happened:

1- On August 18, 2022, the Montreal Canadiens acquired Sean Monahan for free, along with what became the 16th overall pick in the 2025 Draft, in exchange for “future considerations.”

To Montreal: Sean Monahan + 16th overall pick in 2025
To Calgary: Absolutely nothing

2- On February 2, 2024, the Canadiens traded Sean Monahan (who was acquired for free) to the Winnipeg Jets in exchange for a 1st-round pick and a 3rd-round pick.

To Montreal: 2024 1st-round pick + 2027 3rd-round pick
To Winnipeg: Sean Monahan

Note: That 2024 1st-round pick became Michael Hage, after a trade with the Los Angeles Kings.

So if we sum it all up, Kent Hughes went from..

“Future considerations” (a.k.a. nothing)

To:
Michael Hage
16th overall pick in 2025
2027 3rd-round pick

But that’s not all.

Later, Kent Hughes used that 16th overall pick in 2025-acquired completely for free back in 2022-to (yes, really) acquire Noah Dobson!

It’s incredible.

So if we recap and build out the full tree of this absolutely insane trade, the Montreal Canadiens turned..

A 17th overall pick in 2025 + Emil Heineman + future considerations

into

Noah Dobson + Michael Hage + a 2027 3rd-round pick.

This is the kind of trade that can truly reshape a franchise.