How Rudy Giuliani went from a respected federal prosecutor and beloved NYC mayor to Trump's bag man

  • Rudy Giuliani, President Donald Trump's attorney, has been at the forefront of the administration's response to several controversies and legal issues.
  • Giuliani was once the widely hailed mayor of America's largest city who lead the country through national tragedy.
  • Recently, Giuliani became a key player in Trump's impeachment inquiry, found himself under federal investigation, and has represented the Trump campaign's unsubstantiated efforts to overturn the results of the 2020 election.
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Former New York City Mayor Rudy Giuliani has had a high-profile ride from lawyer to New York politician to presidential candidate to President Donald Trump's personal attorney and cable-news defender.

He's also been a larger-than-life public presence who's dabbled in drag, led the country through the tragedy of September 11, 2001, and was a central figure in Trump's impeachment inquiry.

When Giuliani was booed at a Yankees game in 2018, it became clear he had taken on a new reputation that was far from being "America's Mayor" who showed courageous leadership after the 9/11 attacks.

By 2020, his reputation was further complicated as he peddled disinformation and led the Trump campaign's meritless legal efforts to overturn the results of the presidential election. Here's a look at his journey, in photos.

Rudolph Giuliani was born on May 28, 1944 in Brooklyn, New York. Raised on Long Island, Giuliani went on to attend the Bronx's Manhattan College before graduating magna cum laude from New York University School of Law in 1968.


Giuliani is the grandson of Italian immigrants, born to a working-class family comprised of firemen and policemen, which he said gave him an appreciation for public servants. "I grew up with uniforms all around me and their stories of heroism," Giuliani has said.

Source: The Quotable Giuliani: The Mayor of America in his Own Words

Giuliani's first marriage lasted 14 years before it was annulled after he discovered he was second cousins with his wife, Regina Peruggi.

Source: New York Daily News

In April 1984, Giuliani married Donna Hanover on the Upper East Side of Manhattan. The couple later had two children: Andrew and Carolin.

Source: New York Daily News

Giuliani was a popular politician and first elected New York City mayor in 1993.

He was the first Republican elected to the office since 1965.

Source: CNN

His administration had a strong effect on New York's unprecedented crime rates …

… and had a strong public image because of his participation in events like New York's annual roast of the mayor, at which he appeared as his alter ego, Rudy Rudia.

Source: New York Daily News

He was recognized as a brave leader for New Yorkers and the country after the 9/11 attacks, earning the nickname "America's Mayor".

He even was widely favored to be the 2008 Republican presidential nominee.

Source: CNN

But his campaign proved disastrous after a series of missteps including ignoring primaries before Florida, relatively liberal policies, and a complicated family image, causing him to fall from the top of the polls.

Source: The Guardian

But since his exit from his widely popular time as a political candidate, his public image has grown somewhat bizarre.

Ahead of the 2016 election, he made repeated aggressive public comments against former President Barack Obama "doesn't love America" and pushed propaganda to make "people hate the police".

Source: Business Insider, The Hill


He cut a kooky figure when he was pictured wearing Apple AirPods sideways in May 2018.

Source: Business Insider


Giuliani joined, then quickly misstepped, as part of President Donald Trump's legal team.

Source: CNN

Over the course of the second year of the special counsel Robert Mueller's investigation, Giuliani was often at the forefront of changing narratives from Trump's camp on key points of the probe.

Source: Business Insider

Giuliani grew to be a controversial figure after growing closer to the Trump administration and its scandals. Notably, he was booed at a Yankees game after a stadium-wide announcement wished him a happy birthday.

Source: Business Insider 

In one of his many lively television appearances, Giuliani perplexed "Meet the Press" host Chuck Todd in August 2018 with a claim that Mueller could trap Trump in an interview because "truth isn't truth."

Source: Business Insider

Later in August 2018, Giuliani was the first among Trump's associates to admit that the the controversial 2016 meeting at Trump Tower between campaign officials and a Kremlin-linked attorney was to get "dirt" on his Democratic opponent, Hillary Clinton.

Source: Business Insider

Giuliani later waved off investigators' focus on Trump's contact with Russians as a whole, saying that even if there was collusion, "collusion isn't a crime."

Source: Business Insider

By December 2018, Giuliani had also dismissed payments meant to silence women who said they had affairs with Trump, one of whom was porn star Stormy Daniels, as "not a crime," days after Trump's former personal attorney Michael Cohen was sentenced in part for facilitating the payments.

Source: Business Insider

Giuliani was at the center of the Ukraine scandal that prompted the House to launch an impeachment inquiry into Trump. A memo of Trump's phone call with Ukrainian President Volodymyr Zelensky showed Trump said Giuliani would give him a call to talk about Joe Biden's alleged corruption, which hasn't been substantiated.

Sources: Business Insider, House Permanent Select Committee on Intelligence

A whistleblower complaint said Giuliani was a "central figure" in Trump "pressuring a foreign president to investigate one of the President's main domestic political rivals."

Sources: Business Insider, House Permanent Select Committee on Intelligence

Giuliani said he'd be the "hero" in the scandal and called the whistleblower complaint "crap". House Democrats wanted to bring him in for questioning in the impeachment inquiry, but he never testified.

Sources: Business Insider, The Atlantic, House Permanent Select Committee on Intelligence

Giuliani also consulted on Trump's 2020 presidential campaign. He got spoofed by "Borat's daughter", played by Bulgarian actress Maria Bakalova, in Sasha Baron Cohen's movie sequel.

Source: Insider

Some of Giuliani's most controversial work for Trump came at the end of the 2020 election, where he pushed the factually dubious Hunter Biden laptop story and led the Trump campaign's baseless legal efforts to overturn President-elect Joe Biden's victory.

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