What an absolute pain in the ass he must be to deal with. I've had an aquaintance or two who were the litigious types and you just never fully trust them and friendship is impossible on any meaningful level because of their proclivity to sue the shit out of someone when things don't work out how they expected. No thanks.
As an aside there is something to be said about control issues where someone's primary means of reconciliation or 'compromise' is to intimidate whether it is by physical means or lawyering up. Basically, I see peeps like this as bullies.