Should Maple Leafs GM Treliving Hang Up the Phone on an Easton Cowan Trade?

Every once in a while, a reader drops a question that sticks with you about a post you just wrote. Yesterday, it was Jimmy D, who was responding to a post I wrote unpacking the logic of all the trade chatter about the Toronto Maple Leafs' young star, Easton Cowan. I was clear that I didn’t believe the trade should or would happen. That said, looking at it logically gives Maple Leafs’ fans and writers some sense about why such a seemingly improbable trade should be a magnetic attraction for so many.
The reader asked a great question when he wondered out loud whether Brad Treliving would hang up the phone if another GM called about Cowan, especially if the Maple Leafs were hovering just outside a playoff spot and the other GM offered a reliable scoring winger in return.
Easton Cowan Is Good, But Really, How Good? And When Does His Prime Begin?
That’s the kind of question that splits a fan base down the middle. Half of Leafs Nation sees Cowan as a future heartbeat player, and half remains skeptical of his bottom-line future potential. For the former, here’s a kid who plays with the sort of energy you don't find in free agency and almost never in July. The other half, usually the group that watched the last 20 years unfold with calendar-induced skepticism, looks five years down the road and wonders if Cowan’s prime (even if he’s awesome when it does come) arrives right when the team is sliding down the far side of the hill.
And timing might really be the crux of the issue. This might not be so much about whether Cowan is good. He is. You can see it in the way he competes, the way he refuses to be bumped off shifts, the way he lifts lines that are supposed to lift him. Maple Leafs fans have seen enough prospects over the years to know when one has that “fire in his belly.” Cowan does.
The Question for the Maple Leafs Is Timing
The question is timing. Cowan’s story might hit its stride in 2029. The Maple Leafs’ story might not.
You look at the roster math, and it’s not hard to imagine a different skyline by 2029. Tavares has retired, Matthews is perhaps exploring life in a new location, and the blue line is completely reshuffled by age. It’s the simple erosion that happens to every team’s core.
Matthew Knies and William Nylander might be the only familiar faces left when Cowan’s prime arrives. That’s not pessimism — that’s just the NHL clock doing what it always does.
So, Does Treliving Hang Up the Phone?
Jimmy D doesn’t think Treliving slams it down. He might press it against his shoulder, take a long breath, and ask what the other GM has in mind. There’s not a chance he shops Cowan; that’s problematic for several reasons. Still, Treliving would not be doing his job if he didn’t at least listen. A young, right-shot, top-four defenseman who can run your power play? A scoring winger with term and bite? These aren’t players who fall out of trees. They’re also not players you get without feeling a little sick to your stomach.
The Maple Leafs’ window isn’t closed, but the frame is getting snug. When that happens, you don’t make reckless trades. You make calculated ones. So maybe, as the reader hinted, the better question isn’t whether Treliving hangs up. Perhaps it’s whether he can afford to.
