I won't get into a real ranking, especially for a thread that's clearly a troll job. But I will use this as an opportunity to vent a bit. Haters, feel free top enjoy my pain for this one. You have my blessing.
Of all the eerily similar failures, there's only 3 that truly stand out as unique. I'll define them here with no particular order:
2021 vs the Habs. Being the favourite against a huge rival and still blowing it? That was the only one that was a true embarrassment. Not a disappointment, an embarrassment. Montreal was a joy to watch that year, proving you could go so far with only two things that the Leafs didn't have: Heart and a superstar goaltender.
2025 vs the Panthers. This is the only loss that made me mad. I defended the team after all the other losses. Always arguing that the core could get it done eventually, it just didn't come up heads in a close series. But not anymore. This series broke me as a fan. I tossed a jersey in the trash bin, and enjoyed walking it to the curb for pickup. I've done a 180 on players I used to love. I'm mad. And I don't care about the team the same way anymore.
2013 vs the Bruins. This was more than a sporting event for me. I've touched on it on HF in the past, and still won't get into all the details here. But my whole family was going through a tough time, including health issues and a death in the family. Because of this, we were all together already when this game happened, so it was an accidental family reunion. You could feel it in the room, we needed a win. As a family, it felt like we earned something good. Some kind of reward for going through everything together. We needed hope in the world. We needed a positive thing to rally around, we deserved it. And there it was, a Leafs win was materializing, like it was a gift just for us from the Hockey Gods, or God himself. Then the crash was the most demoralizing experience of my life. It was like all the colour in the room turned grey. It was a living definition for the word despair. We were living in reality, without the happy endings. As the overtime played out to silence, there was a crushing understanding that people are mortal. I can still feel the handle of my mother's wheelchair in my hand as the game ended. They lost. We were losing. The moment wouldn't have been darker with a mushroom cloud growing outside the window. With noting to lift our spirits, we were left there with nothing going on except the health problems and grief. Like a goldenticket-less Charlie, sitting in the slanted shack realizing that the book ends at this chapter without the whimsy. Life is pain, highness.