Rudy Giuliani, the former mayor of New York City, has filed for Chapter 11 bankruptcy in New York. In the filing, he lists debts totaling up to $500 million and assets up to $10 million. This move comes one day after a federal judge ruled that Giuliani must immediately pay $148 million to two former Georgia election workers, Ruby Freeman and Shaye Moss. The main debt listed in the filing is the $148 million judgment, which may not be dischargeable in bankruptcy due to willful and malicious acts. Giuliani also owes over a million dollars to lawyers suing him, and he lists potential debts from other lawsuits, including defamation claims from Hunter Biden and Smartmatic, a voting company.

The $148 million judgment is expected to stay with Giuliani for the rest of his life, and while he can appeal, it appears challenging without the necessary bond. The fate of Freeman and Moss's recovery and the extent of Giuliani's assets, including a listed apartment for sale, remain uncertain in this unfolding bankruptcy process. This marks a significant downfall for Giuliani, once known as "America's Mayor."