Rudy Giuliani is probably one of the most controversial figures in the entire nation – not just in the world of law but also in the world of politics and general celebrity gossip. Recently, it was reported that the former mayor had been ordered to pay over $235,000 to his wife as part of a divorce settlement. Giuliani seems determined not to cooperate, which could reportedly see him incarcerated. But is there any real possibility of Rudy going to jail? Remember, this man is an experienced lawyer who knows plenty of courtroom tricks. Is this all part of the plan for Giuliani? 

How it Started

In 2019, Rudy and Judith Giuliani signed a divorce agreement. As part of this agreement, Rudy would provide a settlement of hundreds of thousands of dollars to his former wife. Not only was this a major financial blow for the lawyer, but the divorce proceeding itself was very public – during a time when Rudy was already under the spotlight for his connection to President Donald Trump. During this period, he was accused of concealing assets – allegedly taking money under the table while working “pro bono” for the former president. Judith publicly called him a “liar,” ending any hope of a private divorce handled quietly behind closed doors. 

The Allegations

Over the last three years, the divorce settlement was never really “settled.” The topic is one of continued controversy, keeping both Rudy and Judith in the headlines. The most recent development is the allegation that Rudy has been falling behind on his payments, with Judith stating that she is owed more than $262,000. A Manhattan judge then took her side, warning Giuliani that if he did not hand over at least $225,000, he would be held in contempt of court. 

Normally, being held in contempt of court does not necessarily equate to actual jail time. But this particular judge seems intent on throwing the book at the former mayor, stating, “If the amount is not paid by that date, I’m going to be forced — unfortunately because it’s not something I want to do — I’m going to be forced to remand the defendant into custody.”

According to Giuliani, Judith’s allegations are true – partially. He says that his former wife is owed money – but it is nowhere near the amount that she alleges. He also claims to have proof that he owes less than $235,000 – but he has yet to hand that documentation over to the court. 

Giuliani’s real mistake was simply not showing up to court – something that seriously annoyed the judge. He stated at the hearing: “For him to snub his nose at the court and not bother showing up and appearing in court — God forbid somebody would do that to him when he was US attorney.” 

This is just one of many legal issues that Rudy is currently facing, including a lawsuit filed by an art appraisal firm, election-related charges, and more.