Before President Trump hired Rudolph W. Giuliani to defend him in the Russia investigation, before Giuliani delivered a hotblooded, fists-clenched speech on Trump’s behalf at the 2016 Republican National Convention, the most sensational moment in the duo’s long history came when Trump kissed Giuliani on the breast.
The former New York mayor was dressed in drag. The kiss was part of a spoof show in 2000 for a good cause. Elliot Cuker, the stage director who made it happen, said he picked Trump to pair up with Giuliani because “he’s a terrific actor, period. There was no strong connection between them.”
On the surface, the president and the man he has now turned to for a defense against special counsel Robert S. Mueller III’s investigation of alleged Trump campaign ties with Russia share some similarities. Trump and Giuliani are both street-savvy New Yorkers, Yankees fans and political populists with a passion for straight, blunt talk.
But the notion that Giuliani and Trump have a special bond does not comport with the recollections of people who worked closely with both men in the 1980s and 1990s, when the mayor and the real estate developer were two of the biggest names in the nation’s largest city.
“They were nowhere near close in spirit or how they operated,” said Cuker, a dealer in classic cars who was friends with Giuliani for many years. “Back then, Donald was more concerned with his image, his playfulness, a different kind of narcissism, whereas Rudy was much more conservative, more drawn into himself. I never saw a real bond between them. Whatever relationship they had was convenient for both.”
Both men relished being in the public eye, going to great lengths to build their images. Both were mainstays in New York tabloid headlines and regular guests on David Letterman’s TV show and Don Imus’s and Howard Stern’s radio broadcasts.
“Rudy was prepared to work very hard for applause and so was Donald Trump,” said Wendeen Eolis, a former adviser to Giuliani who runs a legal consulting firm in Manhattan. “Rudy became very well known in the later years for being not just blunt, but also critical for effect, and I think it’s fair to say they share that trait.”
But Eolis said the two men were too different to have been buddies. “I believe Donald is savvy about encouraging relationships, both for his business purposes and his personal convenience,” she said. “I do not recall the name Donald Trump coming to Rudy’s lips in the consideration of a government initiative, only as a reaction to coverage of him.”
Others who worked with the two say it was Trump who sought favor from the mayor, although at least on paper the relationship went both ways.
In 1989, Trump was co-chairman of Giuliani’s first major fundraiser in his first run for mayor; the event pulled in $850,000. But Trump also donated that year to Giuliani’s opponent, Democrat David Dinkins. And the developer said on several occasions that his primary motive in the race was making sure that Mayor Ed Koch (D), with whom Trump had had a long feud, did not win a fourth term.
A decade later, when Giuliani was running for a U.S. Senate seat from New York, Trump again held a fundraiser for him, at $500 a head. About the same time, Giuliani let it be known that he was supportive of a Trump run for president as a Reform Party candidate. Some news reports from the time said Giuliani was drawn to a Trump candidacy because the developer in those days described himself as a “liberal.” (Giuliani at the time was a vocal defender of gun control, gay rights and a path to citizenship for undocumented immigrants.)
Things do change, but Trump’s role in Giuliani’s campaigns remained consistent. He raised money for the former mayor, but not exclusively. In 2007, Trump again chaired a fundraiser for Giuliani, who was considering a run for the Republican presidential nomination. About the same time, Trump held a fundraiser for a presidential candidate seeking the Democratic nod: Hillary Clinton.
Trump went on Stern’s show to explain himself: “I’d like her to win on the Democratic side, Rudy to win on the Republican side,” he said. “I have to, you know, make a decision . . . but they’re both great people, Howard.”
Trump and Giuliani first ran across each other in the 1980s, when Giuliani was U.S. attorney in Manhattan and Trump was cultivating his celebrity in service of building a real estate empire.
Trump was the youngster in a New York rat pack of business bigwigs who would hang out together at a members-only spot called Le Club, or in Yankees owner George Steinbrenner’s suite at the stadium in the Bronx. The group included Steinbrenner, Fox media magnate Rupert Murdoch, Chrysler Chairman Lee Iacocca, and Roy Cohn, Trump’s first and most important lawyer and fixer.
“Donald was the young guy who hung out with them,” said a New York executive who knew the group well, who spoke on the condition of anonymity. “Rudy was much closer to Iacocca and Steinbrenner. He and Donald never really socialized. They were very different people.”
As Giuliani entered politics, Trump became a booster of his career, arguing that the former prosecutor would be good for developers and tough on crime.
But Giuliani was at times wary of Trump. In 1989, after Trump bought full-page ads in New York newspapers calling for the execution of “roving bands of wild criminals [who] roam our neighborhoods,” Giuliani, then running for mayor, said that he didn’t endorse the Trump ads but that they contributed to “a healthy debate.” Trump was then days away from co-chairing Giuliani’s first big fundraiser.
A decade later, when Trump proposed building the world’s tallest all-residential tower on Manhattan’s East Side, Giuliani, still mayor, declined to take a position even as many residents denounced the plan as overbearing and aesthetically overwrought. Neighbors criticized the mayor for his uncharacteristic silence but Trump, asked about Giuliani’s reticence, said, “I am very respectful of his stance.”
The building, which has 72 stories although its elevator buttons go up to 90, was completed in 2001 and held the world record for height for about two years.
Trump and Giuliani did occasionally find themselves on the same side in New York City. They positioned themselves against what Trump called “the civics” — the historic preservationists, housing advocates and social-service providers who often fought his real estate proposals.
But the relationship didn’t blossom until after Giuliani endorsed Trump for president in April 2016, after Trump had vanquished most of the Republican field. Giuliani had been openly skeptical of his candidacy before that, slamming Trump’s proposal to ban immigration by Muslims and pushing back when Trump falsely contended that “thousands” of Muslims had gathered in New Jersey to cheer the collapse of the World Trade Center on Sept. 11, 2001.
After the endorsement, Giuliani’s tone changed. He praised Trump’s suggestion that Giuliani help lead a task force on radical Islam.
“Rudy saw a path to becoming secretary of state, and from then on, he was all in,” said a former aide to Giuliani who spoke on the condition of anonymity to be frank about his ex-boss.
Disappointed when he didn’t get the job as the nation’s top diplomat, Giuliani stepped away from Trump for a time, said several former associates. But he was willing to sign up as the president’s lawyer as a possible step toward a top administration position, they said.
Some of Giuliani’s friends worry that he is reentering Trump’s orbit only to be disappointed by a president who seeks his services for this job alone. They say the two men have used each other through the years, but have no real bond.
Cuker, who put the two together for the 2000 kiss, said his purpose in staging the encounter was to humanize the mayor, then in his second term.
“By that point, everyone thought he was such a b------, so I thought people should see that he has a sense of humor,” said Cuker, who directed the Inner Circle show, a charity event put on by reporters who cover New York politics.
The director said Trump took it upon himself to bury his face in Giuliani’s breast. Trump’s instructions had been only to act as if he were attracted to Giuliani’s voluptuous character, “Rudia.”
“He did the kiss himself,” Cuker said. “He was spontaneous and open to it, and those are the earmarks of a real showman.”