My worst night at poker was -700. Lost a bunch to stupid callers.
The worst hand that night was when I had Aces, the other guy had Ace5 suited. I raised to like 40. Guy Raises to 80. I reraised him all in to like 300 or something. He thinks about it, then says, "I feel like gambling." I flip over my Aces, he started pushing his chips to me. The board comes, King Deuce Four. Yup, he turns a 3.
The other hand, same play, my Kings lost to Qs, preflop all in again. Another 350.
Then I just left and went to set up campaigns.