Playing "What if?" with 6 key Maple Leaf decisions from the Brendan Shanahan era

It’s over. The Brendan Shanahan era is all but done, Mitch Marner is all but gone, and big changes seem imminent in Toronto. The Maple Leafs, or at least this version of them, have failed.

Did it have to be this way?

That’s the big question these days. To hear some tell it, yes, this was the inevitable outcome all along, because playing in a big market like Toronto is just too much to ask from the toughest athletes in the world. Others would tell you that the Shanaplan was doomed from the very start, because it was built around the wrong core. And some would just shake their heads and mutter something about being cursed.

Then there’s the side that says no, it didn’t have to be this way – that there were multiple branching paths along the road that made a different destination possible. That’s the premise of today’s piece, as we look at a half-dozen key checkpoints in recent Maple Leafs history, and wonder what would have happened if a different decision was made.

Our starting point here is 2018 or so. The Leafs have already drafted Auston Matthews, Mitch Marner and William Nylander. They’ve made a surprise playoff run in their first year together, then nearly knocked off the established Bruins in year two. Brendan Shanahan has a plan, and it’s working. While there’s a long way to go, the future is as bright as it’s ever been.

And then… well, we know what comes next. But what if? We won’t go too deep down the alternate history hole on any of these – if you’re looking for fan fic that ends with the Leafs winning all the Cups, you’ll have to write it yourself – but each is worth exploring. And at the end, I'll even let you tell me the right answer.

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