Rudy Giuliani is finally circling the drain

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Rudy Giuliani has become something of an expert on circling the drain. Giuliani’s fall has been long and deep, gaining momentum in recent years thanks to his slavish embrace of Donald Trump. After achieving hero status with the nickname “America’s mayor,” being named as Time magazine’s 2001 Person of the Year, and receiving an honorary knighthood from the late Queen Elizabeth II in early 2002, Giuliani’s life is now all about testing the bottom.

Of all the reasons why Giuliani could soon see the inside of a cell, failure to pay alimony now looms large. At a hearing on Friday, a New York judge warned Giuliani that if he doesn’t pay $225,442 to his third ex-wife, Judith, plus attorney fees by October 7, he will “be forced to remand the defendant into custody.” The judge didn’t address Giuliani directly because he somehow failed to attend the hearing (due to an alleged “misunderstanding,” as he toldf the New York Post).

Giuliani also has still not provided any evidence to refute the alimony claim. At the prior hearing, in August, Giuliani disputed the amount but admitted “[i]t’s totally my fault.” Giuliani also tried what could be called the circling-the-drain defense, complaining to the judge that “I’m being sued in ten different cases. I’m getting ready for two massive hearings,” according to an earlier Post report.

In another development, Giuliani is now the big loser after accusing Daniel Gill of assaulting him at a New York City supermarket in June. According to Giuliani, Gill slapped him so hard it felt “as if a boulder hit me” or “like somebody shot me.” Subsequent video footage painted a different story, however, with Giuliani hardly reacting to the touch. This turn of events prompted New York City Mayor Eric Adams to suggest his office will investigate Giuliani for falsely reporting a crime.

On Wednesday, Gill accepted a deal in which all criminal charges will be dismissed in six months assuming he engages in no criminality. This comes as a blow to Giuliani’s credibility, whose claims led to Gill getting charged with assault with intent to cause physical injury, harassment in the second degree, and menacing in the third degree.


With his name cleared, Gill proceeded to file a notice of claim (a lawsuit prerequisite) against New York City for $2 million. Gill explained that Giuliani’s claims of serious injury from Gill’s “assault” made him lose his job, embarrassed him, and has been “traumatizing,” as he told the New York Times. Giuliani is running out of ways to continue circling the drain.

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