SCOTT SIMON, HOST:
Rudy Giuliani is at the center of the Ukraine scandal. This clip of the president's personal attorney on CNN with Chris Cuomo went viral.
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CHRIS CUOMO: So you did ask Ukraine to look into Joe Biden.
RUDY GIULIANI: Of course I did.
CUOMO: You just said you didn't.
GIULIANI: No. I didn't ask him to look into Joe Biden. I asked him to look at the allegations...
SIMON: Rudy Giuliani's been at the center of allegations this week that President Trump pressed the president of Ukraine to investigate the former vice president.
From member station WNYC, Andrea Bernstein, the co-host of the Trump, Inc. podcast, traces Mr. Giuliani's path from corruption-busting prosecutor to being the center of an impeachment probe.
ANDREA BERNSTEIN, BYLINE: Back in 1989, when Rudy Giuliani first ran for mayor of New York City, he was genuinely admired for his anti-corruption credentials.
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SUSAN MOLINARI: Please stand and welcome the next mayor of the city of New York, Rudolph Giuliani.
BERNSTEIN: As the U.S. attorney for the Southern District of New York, Giuliani helped break the back of the Mafia. He personally tried and won a conviction of a former Democratic Party official of the Bronx, a close associate of attorney Roy Cohn.
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GIULIANI: I saw the corrupt politicians who take money from our seniors and our children to line their own pockets.
BERNSTEIN: He didn't win that year. But four years later, he became the first Republican mayor in the city in a quarter century. He ran New York as a crime-busting, welfare-cutting, no-nonsense chief executive, who wasn't afraid to make fun of himself, like in this video made for a celebrity roast in New York with Donald Trump. Rudy Giuliani dressed up in a blond wig and an iridescent, lavender dress, speaking in falsetto.
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PRESIDENT DONALD TRUMP: You know, you're really beautiful. And a woman that looks like that has to have her own special scent.
GIULIANI: Oh, thank you.
BERNSTEIN: The camera pulled in for a close-up as Donald Trump lowered his face into Giuliani's decolletage. Giuliani returned a high-camp slap.
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GIULIANI: Oh, you dirty boy, you. Oh, oh.
BERNSTEIN: Trump gave generously to Giuliani's campaigns. Giuliani helped his business. Giuliani ran for Senate for a while against Hillary Clinton. After contracting prostate cancer and separating from his second wife, he dropped out of that race. He became increasingly combative. New Yorkers were tiring of him. Then it was September 2001.
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GIULIANI: The South Tower collapsed. A number of people had to evacuate.
BERNSTEIN: I was in the press pool in the aftermath.
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BERNSTEIN: Anybody have another mask?
We followed Giuliani as he toured Ground Zero.
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GIULIANI: And we're somehow going to manage our tremendous grief and our loss. But then we're also going to have to rebuild the city and make it even stronger than it was before.
BERNSTEIN: The nation fell in love with him.
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OPRAH WINFREY: America's mayor is the mayor of New York City.
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WINFREY: Ladies and gentlemen, Rudy Giuliani.
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BERNSTEIN: Over the next two years, Giuliani went into business. He had clients like Purdue Pharma, the government of Qatar, Merrill Lynch. Public disclosures show he left City Hall with a bit over a million dollars in assets. Five years later, he was worth between $20 million and $70 million. In 2008, he ran for president. Right up until December of 2007, he was the frontrunner. The weekend before the Florida Republican primary, he campaigned in Boca Raton. At a synagogue there, Carol Hornish was one of many New Yorkers who had moved to Florida.
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CAROL HORNISH: He cleaned up the dog doody. He cleaned up the washing - the guys that washed. And Times Square was great. He made it friendly for my grandchildren. So I'm here now. However, I'm a Democrat.
BERNSTEIN: He had his fans. But it was hard for him to live up to his TV image. Republicans chose John McCain to be their nominee instead. Giuliani continued to sell his services - public speaking, security consulting - around the globe in Mexico, South America and Ukraine. In 2016, he got behind an old friend.
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GIULIANI: Thank you, New York...
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GIULIANI: ...For a New Yorker for once on the ticket, Donald Trump.
BERNSTEIN: During the campaign, Giuliani was one of Trump's most loyal surrogates. After the "Access Hollywood" tape was released, Giuliani did interviews on five Sunday morning shows.
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GIULIANI: The fact is that men, at times, talk like that - not all men. But men do.
JAKE TAPPER: You've talked like that?
BERNSTEIN: After Trump won, Giuliani continued to travel around the world to do speeches and make business contacts, frequently flying to Ukraine in the former Soviet Union. Giuliani signed up as Trump's unpaid private attorney in the Mueller probe. He became more and more vocally supportive of Trump, defending him vehemently when Mueller said he could not exonerate the president of obstruction of justice.
Now Giuliani has gone further than claiming the Mueller probe was a witch hunt. Giuliani repeatedly met with Ukrainians to try and convince them to intervene in a way that could help Trump's next campaign in 2020. Giuliani spoke about his actions recently on CNN.
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GIULIANI: I asked them to look into the allegations that are related to my client, which tangentially involve Joe Biden...
BERNSTEIN: In the whistleblower complaint delivered to Congress this week, the intelligence official wrote about this foreign interference. The president's personal lawyer, the whistleblower wrote, Mr. Rudolph Giuliani, is a central figure in this effort. For NPR News, I'm Andrea Bernstein in New York.
SIMON: Andrea Bernstein is co-host of the Trump, Inc. podcast, which is a co-production of ProPublica and member station WNYC. Their episode on Rudolph Giuliani and Ukraine drops on Wednesday. Transcript provided by NPR, Copyright NPR.