Wasn't alive for it and every real trade between '88-'91 pretty much pisses me off. The amount of talent that slipped past the Leafs is unreal.
As a hockey fan born in '91 whos first real memories were probably the 99 playoffs, I'd have to probably say the one major thing that irked me most was the Leafs 2013 Offseason. I didn't know **** about Rask, so I didn't really have any attachment when he was traded, 2003 wasn't a thing yet so you couldn't be mad when you were loading up on hall of famers like it was NHL2003, Kessel, while a bad trade, didn't really bother me since he was good but the team was bad and he always seemed like a genuinely good guy you wanted to root for.
I was never a big big Sundin fan, so the way he left didn't bother me, but the trade rumors about Kaberle always made me wish they pulled off one of those rumored Carter-for-Kaberle swaps.
That said, the 2013 Offseason kicked off in heartbreak, and I wanted so bad for the Leafs to fire Carlyle, I blamed him for everything, the complete blunder that was the third period rested on the shoulders of the man who is supposed to be playoff tested. They retained him, then the Luongo rumors started, and I thought it'd be great because finally the Leafs starting goaltender woes would be over. Then we got Bernier, who never really demonstrated he could outperform Reimer, who had kept us in that 7 game series, in a bad deal and signed him to a worse contract. Then Grabovski, the one guy who seemed to always play with his heart on his sleeve, the guy that everybody in TOronto pretty much loved (and in retrospect would've been a good triggerman on a Marner line), gets complianced, despite being arguably the best center the Leafs had at that point, while Liles sat on the third pairing like a bum. Lupul still had good trade value, only being one season behind his all star appearence. And then they sign Clarkson, and you get a little optimistic that the guy who only Ovechkin outshot, would be able to be like a discount Lucic, and that goes to ****.
The whole offseason just seemed to be stupid move after stupid move, treading water and setting the franchise up for failure. Its probably the angriest I've been in the heat of the moment where you had to question how these people were in charge and even inspired that PPP article about Nonis being outdone by a potato.