It's the Gilmour trade easily. It gutted a potentially championship roster overnight. It took the Flames from perennial cup favorite status to 1st round exit fodder....and eventually the team turned into the hot mess of the Young Guns era.
The Gilmour trade was the very day that the Flames began their decline. They've never been close to that level since.
I will despise Risebrough for the rest of my days purely for how he handled those years.
This thread makes me sad.