All he had to do was put his fortune in a money market account and just live off the interest, but his stupid ego is way too big to just simply enjoy life.
I'd bet decent money that he didn't choose to take on the Trump loss but Putin made him. He had to know how poorly his day in court was going to go. The whole thing had the vibe of someone following through with an assignment that was way over their head and decided to just bullshit his way through it.
Gets in bed with the most underhanded, backstabbing, serial lying, and out right hemorrhoid of an individual; and this will happen. There's not a single person on earth Trump will not screw over for a buck.
He tried to not bring charges, but when he declared bankruptcy his creditors were basically able to force him to pursue debts owed to him regardless is what he actually wanted.
Always wild to me that Giuliani absolutely could have rode that America's Mayor shit (from literally just being NYC mayor on 9/11) into the sunset (or maybe a commentator spot on Fox) and done absolutely fine for himself... but got fucked up on hubris and joined forces with Donald "Make lawyers get lawyers" Trump. Well, reap what you sow shitass