Trumpworld distances itself from Rudy: The inside story of Giuliani's descent from 'America's Mayor' to presidential lawyer and now an FBI target

  • Former Trump aides told Insider they were not surprised that the FBI raided Giuliani’s apartment.
  • The New York Times first reported the raid, which collected Giuliani’s electronic devices.
  • Giuliani hasn’t been in Trump’s orbit since January 6.
  • See more stories on Insider’s business page.

The erratic aria of Rudy Giuliani was always going to end like this — with a crash. 

Early Wednesday, federal investigators raided the Upper East Side apartment of President Donald Trump’s former lawyer and New York City’s former mayor. 

Central to the FBI’s investigation: whether Giuliani illegally lobbied the Trump administration at the behest of Ukrainian oligarchs or otherwise violated federal foreign influence laws. In interviews with Insider, eight current and former Trump and GOP officials alternately lamented and blasted the former Giuliani’s long fall from grace. 

“This was always just a matter of time,” one former Trump 2016 adviser said of the man many Americans once hailed in the gauzy, post-9/11 zeitgeist as “America’s Mayor.” 

“People should raise their eyebrows and recognize this could be much more serious than has been advertised so far,” a former Trump White House official told Insider.

“He was just a reckless guy who would join whoever would pay him,” another former Trump White House official said. 

Read more: DOJ’s investigation of Rudy Giuliani is creating legal headaches for lobbying and public affairs firms that failed to disclose ties to Trump’s lawyer

News that federal investigators had seized Giuliani’s electronic devices — first reported by The New York Times — is only the latest turn in the tumultuous saga of one of the nation’s most visible public figures.

Far from his days as a measured and decisive leader in the midst of national crisis, the Rudy Giuliani of late is prone to pop-eyed diatribes, conspiracy theory-laden TV appearances, and incidents bordering on the inexplicable — his hand-in-pants appearance in “Borat Subsequent Moviefilm” proved a particular low point. Then there was Giuliani’s now-infamous post-election press conference at Four Seasons Total Landscaping in Philadelphia, wedged between the Delaware Valley Cremation Center and Fantasy Island adult bookstore. 

The president’s former personal lawyer, Michael Cohen — whose own home and office were raided three years ago in connection with an investigation that included campaign finance violations, tax evasion, and his work as an unregistered foreign agent — appeared particularly giddy over Giuliani’s misfortunes. On Twitter, Cohen expressed schadenfreude at the news, tweeting “Here we go folks!!!” and later adding, “As I have said many times…they will all be held responsible for their own #DirtyDeeds.” 

In a text exchange with Insider, Cohen declined to comment further. “Not going to be making any comments today,” Cohen said. “Not today.” 

Giuliani, who did not speak publicly Wednesday despite rumors of a news conference, did have some defenders come forward.

New York gubernatorial hopeful Andrew Giuliani, Rudy Giuliani’s son, defended his embattled father Wednesday, railing against the politicization of the Justice Department to a throng of reporters. 

“If this can happen to the president’s lawyer, this can happen to any one of us,” he said in New York City. “Enough is enough!” 

Trump confidant Lindsey Graham said he’s skeptical of federal probes “given what I’ve seen by the FBI and the Mueller investigation.” 

“We’ve been told a thousand times that everybody in Trumpworld was a Russian agent. It turned out to be not accurate,” the South Carolina Republican senator told reporters on Capitol Hill. “I don’t know if this is a continuation of that.” 

He added that “Rudy, like everybody else is presumed innocent,” and said search warrants can be easily obtained “depending on who the judge is.” 

“The past abuse of power should alarm everyone,” Graham said.

On Wednesday, Insider’s attempts to reach Giuliani himself were unsuccessful. Giuliani’s personal lawyer, Robert Costello, also did not respond to Insider’s requests for comment, though he did tell The New York Times his client had offered to answer questions posed by prosecutors except ones that are privileged because they involve Trump.

“What they did today was legal thuggery,” Costello said, according to the Times. “Why would you do this to anyone, let alone someone who was the associate attorney general, United States attorney, the mayor of New York City and the personal lawyer to the 45th president of the United States.” 

Now, a lot of people who know Giuliani act like they don’t know Giuliani anymore. Jason Miller, a Trump spokesman who back in 2008 worked on Giuliani’s ill-fated presidential bid, did not return Insider messages seeking comment. Jay Sekulow, a longtime Trump personal attorney who partnered with Giuliani to defend the president during Robert Mueller’s Russia investigation, declined to comment. And one former Trump advisor told Insider Giuliani hasn’t been in Trump’s orbit since January 6.

The Department of Justice declined to comment.  

Trump, for his part, was also silent on the development — mostly.

“I need you now more than ever,” Trump implored supporters in a 5 pm fundraising text message for his twin political action committees. The message made no specific reference to Giuliani.

‘A union that was going to be hard to break’

Giuliani’s long fall from America’s Mayor to Trump’s hatchet man was years in the making — dating back to at least three months before Trump’s infamous ride down an escalator at Trump Tower to announce his own presidential campaign. 

That’s when Giuliani’s bizarre and often erratic descent into the darkest corners of American politics began at a private dinner in March 2015 at the 21 Club, a Midtown Manhattan Trump haunt. There, Giuliani claimed then-President Barack Obama didn’t love America. 

Giuliani’s journey continued in 2016, when he delivered a 2016 Republican National Convention speech unleashing a barrage of criticism of fellow Empire Stater Hillary Clinton. 

And it culminated in Giuliani’s late-career reinvention as Trump’s personal fixer and attack dog. He worked with Sekulow and the White House to beat back the Mueller probe and spare the president from any criminal charges. But in the celebration from the special counsel’s work reaching its anti-climatic end Giuliani found himself smack in the middle of another scandal as Trump’s attention turned to his 2020 reelection bid.

Giuliani attempted to dig up dirt on Hunter Biden, Joe Biden’s son, and his ties to Burisma, the Ukrainian energy company. When that scandal exploded in public, it paved the way for Trump’s first impeachment in late 2019. 

Read more: Democratic insiders lament how Biden’s big address to Congress spelling out his agenda now must compete for the public’s attention with the Giuliani DOJ probe

In recent years, Giuliani also developed a reputation for his often very public alcohol consumption. He was known to spend afternoons sipping scotch at locales such as the swanky Ten Pound second-floor bar at the Montage in Beverly Hills, California, or draining Bloody Marys with a reporter at the Mark Hotel. 

Back in DC, Giuliani was a fixture at the Trump International Hotel, a sort of Rick’s Café for the Make America Great Again set. He also developed the habit of frequently butt-dialing prominent journalists even as he fancied himself a cybersecurity expert. 

Giuliani’s presence in the Trump White House was long a spot of contention for some senior officials, including John Kelly, then the chief of staff, and Ty Cobb, a top lawyer for the president during the Mueller investigation. Both men expressed reservations about the former New York mayor’s role advising Trump, according to a former senior Trump administration official. But they also recognized Trump and Giuliani had a long past dating back decades to New York. “My Rudy” was the nickname the president gave him. The two even shared a romantic moment of sorts during a comedy skit in which Giuliani dressed in drag and Trump buried his face in his chest.

“That was a union that was going to be hard to break,” the former Trump official said. 

Rudy Giuliani delivers a speech on the first day of the Republican National Convention on July 18, 2016 at the Quicken Loans Arena in Cleveland, Ohio.Brooks Kraft/Getty Images

Trump’s personal legal lion

Giuliani and Trump have had a relationship dating back more than 35 years, but one Trump advisor told Insider Giuliani has been out of Trump’s orbit since January 6. 

For weeks after Election Day, Trump cast Giuliani as his personal legal lion, a lawyer who’d stop at nothing to reveal widespread voting fraud, and ultimately, overturn the results of the 2020 election.

Trump also frequently used Giuliani as a post-election fundraising prop.

“Rudy Giuliani is exactly right. I was WAY AHEAD of Joe Biden on Election Night, and yet, when we woke up the next morning, I was down. How is that possible?” Trump wrote to supporters on November 20, urging them to rush $5 or more to a joint fundraising committee composed of Trump’s presidential campaign, Trump’s Save America political action committee, and the Republican National Committee.

Several days later, these Trump committees asked backers to send more money because “Rudy Giuliani and the Trump Campaign legal team have reportedly uncovered MASS amounts of VOTING IRREGULARITIES.” 

But Giuliani would accomplish no such thing. Giuliani literally melted down at one post-election news conference as a black liquid trickled from his hair to his sweat-drenched temples. Meanwhile, efforts by Trump’s legal team to challenge presidential election results and overturn voters’ verdicts repeatedly failed as December 2020 bled into January 2021.

On January 6, as Trump rallied supporters for a last-ditch “Stop the Steal” rally just south of the White House, Giuliani provided perhaps the most overt call to violence in the moments before a mob of insurrectionists stormed the US Capitol.

“Who hides evidence? Criminals hide evidence … Let’s have trial by combat,” Giuliani told the crowd, some members of which carried weapons or items they’d fashion into such.

Giuliani later said the “trial by combat” line was simply a “Game of Thrones” reference, not him urging Trump supporters to attack congressional lawmakers in the midst of certifying electoral votes that give Biden the presidency.

But Trump by then had soured on Giuliani, dumping the former New York City mayor as his personal lawyer. Come February, Giuliani was nowhere near Trump when the ousted president endured his second impeachment trial in as many years.   

Rudy Giuliani and Donald Trump had a very close relationship — until they didn’t.Drew Angerer/Getty Images

‘No question this is politically motivated’

Former Trump aides argued that the federal investigation into Giuliani was politicized.

“I find it ironic that the investigation has ramped up on Rudy who is primarily being investigated for probing Hunter issues, but the FBI have yet to move on Biden despite having evidence since December 2019,” said a former Trump adviser. 

This person added: “He is definitely in trouble but no question this is politically motivated.”

In late 2019, Giuliani, a fan of the opera since high school, attended a Vienna performance of Tosca after his trip to Ukraine on a mission to find dirt that would unravel — or at least muddy — the first of the two impeachment cases against Trump. 

But now Giuliani’s has become a sort of tragi-comedic figure — something of an operatic character in his own right, according to a GOP source who spoke with Insider on the condition of anonymity. The man who came of age in President Ronald Reagan’s 1980s-era Department of Justice, who was, himself, a former prosecutor in the US Attorney for the Southern District of New York, is now a subject of a criminal investigation. 

“He was out of control, he was burning the candle at both ends,” one Republican who has worked with Giuliani in the past told Insider. “He’s no longer America’s Mayor. The guy’s a mess.”


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