Rudy Giuliani 'is in an excruciating legal predicament — and could very well flip': legal experts

Former New York City Mayor Rudy Giuliani served as the U.S. Attorney for the fabled Southern District of New York, but is now facing such legal peril he might flip on former President Donald Trump, according to analysis by legal experts.

The situation was examined by New York magazine under the headline: "Rudy Giuliani Is (Probably) Screwed: Former prosecutors say he is in an excruciating legal predicament — and could very well flip."

"Has any political figure in recent years fallen farther and harder than Rudy Giuliani?" author Peter Stone asked. "Giuliani is being treated, by all appearances, as a dead man walking. America's Mayor, as he was once known, has been abandoned by his most powerful friend. He has lost his megaphone at Fox News and is now going around with a begging bowl for money."

Stone interviewed former Department of Justice Inspector General Michael Bromwich.

"Giuliani is facing a set of challenges unlike anything he's dealt with before," Bromwich said. "The extremely serious criminal investigation that could send him to jail, the civil suits that could bankrupt him, the disbarment proceedings that may well end any opportunity to practice law ever again — it's a tidal wave of problems with potentially devastating personal and professional consequences."

"It's hard to think of any analogous case where a person who once rode so high — as a prosecutor, a New York mayor, a serious presidential candidate, and an international figure — has been brought so low in so many ways and where the damage has been entirely self-inflicted," he said.

A former acting chief of the Justice Department's fraud section, Paul Pelletier, noted the toll the investigations are likely taking on Giuliani.

"The emotional and financial pressure of a single long-term federal white-collar investigation can take a crippling toll on any target of such an investigation," Pelletier explained. "Enduring multiple investigations, in addition to bar disciplinary actions and financial pressures, creates an enormous incentive to alleviate that pressure in some way. The only logical ways I know of are to plead guilty, cooperate, or both."

He also offered a prediction of what happens next.

"If past is prologue, the search warrants conducted on the phones and electronic devices of Giuliani and his associates should soon begin bearing a cornucopia of fruit," Pelletier said. "That type of electronic evidence typically reveals compelling evidence of the criminal scheme outlined in the search-warrant affidavit. If and when that happens, the walls should close in pretty quickly on Mr. Giuliani and any identified criminal cohorts."

Read the full analysis.