Giuliani made millions of dollars doing security consultation around the world. I can't fathom how he would be broke.
That depends on lifestyle. Also, he probably fronted a lot of costs associated with Trump's defense that he got stiffed on along with his actual pay, so don't discount how expensive that could be. He may be near broke in terms of liquid assets, but he probably has his house and other assets he could sell.
Time to make some money: the business career of Rudy Giuliani
This story dated 2019 sheds some light on the amount of money he earned and does describe expensive lifestyle creep but he made tens of millions of dollars at the very least.