My worst time on toribash would be either when I got scammed out of one of the most stable stable flames in the game by roflmao451, or whenever I lost one of my favorite flames in a duel to one of tay's alts then later found out that he gave it to someone for free because he didn't like it. :/
Yes I am notaboss, this is the account that happened on. :P
Found it pretty funny when the guy who scammed me (who had been a member for two years) got perma banned and I got my money back, but it was doubled, so instead of getting 40k, I got 80k + Some items. <3 Gum.
I think the worst thing to happen to me, or atleast the worst thing I did was being banned for being an asshat on someone's clan thread. It's in the hall of shame somewhere, I'm sure.