Bad clients

Been dealing with a client who is a massive pain. Very argumentative and essentially refuses to be a part of the process or any help. This is not a situation where they are checked out and not part of the operations anymore. Noticed the client will start one offing me and send me personally nasty emails pretty consistently now when we reach out. Just think its funny they think Im scared of them or am just not gonna shoot the email up the chain and laugh at them. Anyone else deal with this or understand the dropping people off chains to try to get away with behavior like this? Thought it was just funny in the grander scheme. Brings up a bigger discussion. What was the worst client you've ever had to deal with and how crazy did things get?

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