Former Speechwriter for Rudy Giuliani Calls Feds Raid 'Tragic Third Act' to His Legal Career

A former speechwriter for Rudy Giuliani called Wednesday's raid of Giuliani's Manhattan apartment a "tragic third act" to his legal career.

John Avlon, a former Giuliani staffer, said he was "shocked" when he found out that federal investigators executed a search warrant against Giuliani and seized multiple electronic devices from both his office and home in New York City.

"[The raid had] A real sense of the tragedy…given the trajectory of his career," Avlon told CNN's New Day on Thursday. "Before he was New York City mayor—when I worked for him and was proud to do so—he was a crusading U.S. attorney leading the Southern District, which is the organization that's investigating him now."

"I don't think you can underestimate the respect he had in the legal community and the justice community, particularly at that time, when he was mayor," he added. "For this sort of tragic third act in the Rudy opera to be punctuated by the feds raiding his apartment is truly stunning, is sickening."

Avlon prepared Giuliani's addresses for the State of the City from 1999 to 2001 when Giuliani was the mayor of New York City and went on to served as the chief speechwriter and the deputy director of policy for Giuliani's 2008 presidential campaign.

Before Giuliani was elected as mayor, he was appointed to be the U.S. Attorney for the Southern District of New York in 1983 by then-President Ronald Reagan. The office is considered one of the highest profile in the country and known for being very independent and nonpartisan.

During his time in that post, Giuliani led the federal prosecution of New York City Mafia bosses in the 1980s known as the Mafia Commission Trial, which led to the conviction of eight organized crime figures.

However, Giuliani's legal reputation has declined since then, especially in recent years as he became former President Donald Trump's personal attorney. In the past year, he represented Trump in a series of failed lawsuits seeking to overturn the results of the 2020 presidential election.

Rudy Giuliani Feds Raid Ukraine
Rudy Giuliani talks to journalists outside the White House on July 1, 2020. Giuliani's New York City apartment was raided on Wednesday by federal investigators. Chip Somodevilla/Getty

"It was also a remarkable moment in Mr. Giuliani's long arc as a public figure," reporter at The New York Times, who broke the feds raid, noted on Wednesday. "As mayor, Mr. Giuliani won national recognition for steering New York through the dark days after the September 11 attacks, and earlier in his career, he led the same U.S. attorney's office in Manhattan that is investigating him now, earning a reputation as a hard-charging prosecutor who took on organized crime and corrupt politicians."

On Wednesday, FBI agents executed a search warrant in connection to Giuliani's ties to Ukraine. Federal authorities have largely focused on whether the former mayor illegally lobbied the Trump administration on behalf of Ukranian officials, who were allegedly digging up dirt on Trump's then-rival President Joe Biden and his son, Hunter.

The search warrant against Giuliani had been blocked by the Justice Department under the Trump administration for nearly two years, but the objections were lifted earlier this year after Merrick Garland was confirmed as Biden's new attorney general.

While Giuliani's lawyer, Robert Costello, called the search warrants a "corrupt double standard" against Republican officials, Avlon said he doesn't believe the investigation is in any way politicized.

"I don't think it's evidence of a politicized justice department," Avlon said. "I think that's kind of an ironic accusation by people from the Trump orbit, but it is tragic and [Giuliani] deserves to be remembered for more than this last act. But I'm afraid it will overshadow his other accomplishments."

Newsweek reached out to Giuliani's team for further comment but did not hear back before publication.