Wednesday, November 19, 2025

All 29 times the Leafs have traded away a first rounder, ranked from best to worst

I love trades and I love rankings, and I’m a Maple Leafs fan so it goes without saying that I love misery. For today’s post, I figured I’d combine all of those things into one piece, with a ranking of all the times that the Maple Leafs have traded away a first-round pick. After all, it feels like a timely topic right about now.

After some digging, I found there have been 29 separate trades in Leafs history in which they’ve traded away a total of 31 first-round picks, so I did what any normal person would do and ranked them all, from the ones that turned out best to worst.

Two things surprised me about that. First, 29 seems low. The Leafs seem to do this kind of thing a lot. I was pretty sure Brad Treliving had traded away 29 firsts on his own, although I guess the math doesn’t quite work out on that one. Give him time, guys, he’s working on it.

The second surprise was the best-to-worst part, since that implies that some of these trades have worked out in the Leafs’ favor. I didn’t think they’d all be disasters, mind you, because some of these are going to be boring draft floor swaps that nobody even remembers. But finding actual wins? Impossible. Or so I thought.

It goes without saying that we're doing this with total benefit of hindsight, which isn't fair to the GMs but too bad for them. Let's go on this journey together...

>> Read the full post at The Athletic




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