Rudy Giuliani is broke. Or at least, that is what he has been telling anyone with a gavel for the better part of two years. It is a wild fall for the man once dubbed "America’s Mayor," now facing a mountain of debt that looks more like a mountain range. When a jury hit him with a $148 million judgment for defaming Georgia election workers Ruby Freeman and Shaye Moss, the immediate question wasn't just if he would pay, but how he possibly could.
Honestly, the numbers are dizzying. We are talking about a guy whose primary income recently included a social security check and a now-canceled radio show.
The $148 Million Wall
The core of the issue is that massive $148 million defamation payout. It stems from a 2023 trial where jurors heard how Giuliani’s false claims about the 2020 election upended the lives of Freeman and Moss. They faced death threats and harassment. The jury didn't just want to compensate them; they wanted to send a message. But a message doesn't pay the bills.
Giuliani’s response was swift: he filed for Chapter 11 bankruptcy. This was a classic legal maneuver. It effectively froze the ability of the election workers to collect their money. For a few months, everything sat in a weird kind of limbo. Giuliani claimed his assets were somewhere between $1 million and $10 million.
That sounds like a lot to a normal person. But when you owe $148 million? It’s basically loose change under the sofa cushions.
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Why the Bankruptcy Strategy Failed
The bankruptcy court wasn't exactly a friendly place for Rudy. U.S. Bankruptcy Judge Sean Lane grew increasingly frustrated with what he called "uncooperative conduct." He eventually threw the whole case out in mid-2024. Why? Because Giuliani was a "recalcitrant debtor." He wasn't disclosing where his money was coming from, and he wasn't hiring the accountants the court demanded.
Basically, the judge felt Giuliani was using bankruptcy as a "pause button" rather than a path to actually paying his debts.
Once that bankruptcy shield vanished, the floodgates opened. Freeman and Moss moved fast. They went after his Mercedes-Benz—a 1980 model once owned by Lauren Bacall—his luxury watches, and his $5 million Manhattan apartment. In late 2024, a judge ordered him to turn them over.
The Surprising 2025 Settlement
By the time 2025 rolled around, things took a turn that most legal observers didn't see coming. In January 2025, after being found in contempt twice, Giuliani reached a settlement with Freeman and Moss.
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The deal was sort of a "peace in our time" moment for the litigation. Here is what happened:
- Giuliani got to keep his Florida condo.
- He kept his three World Series rings (which he claimed he’d already given to his son).
- He promised to never defame the women again.
- In exchange, he provided "unspecified compensation."
By February 2025, court filings officially stated that the $148 million judgment was "fully satisfied." Now, did he actually hand over $148 million in cash? Almost certainly not. The "compensation" likely involved the assets he had already surrendered—like the New York apartment and the watches—combined with whatever liquid cash he could scrape together from his retirement accounts and business entities.
The women essentially traded the pursuit of a massive, uncollectible number for a smaller, immediate payout and the legal right to live their lives without him mentioning them on a podcast ever again.
Where Does the Money Go Now?
Even though the Freeman and Moss saga has technically "satisfied" its judgment, Giuliani isn't out of the woods. He’s still dealing with a laundry list of other creditors. He owed $400,000 to a forensic accounting firm just for the bankruptcy mess. He has millions in potential judgments from other lawsuits, like the one from Dominion Voting Systems.
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His lifestyle has definitely taken a hit. He’s complained in court about not having a credit card or a car. He even mentioned that stop orders were put on his bank accounts, leaving him effectively cash-poor.
What This Means for Future Defamation Cases
The Giuliani case is a massive case study in "judgment proofing." It shows that you can win a $148 million verdict, but if the person you're suing doesn't have $148 million, the court can't manifest it out of thin air. However, it also shows that you can’t just hide behind bankruptcy if you aren't willing to be transparent.
If you are following this for the legal precedent, the takeaway is clear: the courts will eventually lose patience with a debtor who plays games. Giuliani lost his most prized New York real estate because he couldn't—or wouldn't—play by the bankruptcy rules.
Actionable Insights for the Future
If you're tracking these high-profile defamation payouts, keep an eye on these specific points over the next year:
- Watch the Liens: Look for public records regarding Giuliani’s Florida property. Even if he "kept" it, there may be liens that prevent him from ever selling it without the proceeds going to creditors.
- The "Rudy Coffee" Factor: Giuliani has turned to various side hustles, like selling his own brand of coffee, to generate liquid cash. This is a common tactic for high-profile debtors trying to maintain a lifestyle while their main assets are frozen.
- Appellate Rulings: Although the settlement has closed the Freeman and Moss case, other lawsuits are still in the pipeline. The outcome of those will determine if he’s ever truly "free" of his financial burden or if he'll be in court for the rest of his life.
The era of Rudy Giuliani as a multi-millionaire power broker is over. He's now in survival mode, trading his remaining symbols of status for enough legal breathing room to keep a roof over his head.