Podell pleaded guilty to conspiracy and conflict of interest for accepting more than $41,000 in campaign contributions and legal fees from a Florida airline to obtain federal rights for a Bahama route.

The Washington Post later reported, "The trial catapulted future New York mayor Rudolph Giuliani to front-page status when, as assistant U.S. attorney, he relentlessly cross-examined an initially calm Rep. Podell.

Riina allegedly was suspicious of Giuliani's efforts prosecuting the American Mafia and was worried that he might have spoken with Italian anti-Mafia prosecutors and politicians, including Giovanni Falcone and Paolo Borsellino, who were both murdered in 1992 in separate car bombings.

[81] On election day, Giuliani's campaign hired off-duty cops, firefighters, and corrections officers to monitor polling places in Manhattan, Brooklyn, and The Bronx for cases of voter fraud.

In Giuliani's first term as mayor, the New York City Police Department – at the instigation of Commissioner Bill Bratton – adopted an aggressive enforcement/deterrent strategy based on James Q. Wilson's "broken windows" approach.

This involved crackdowns on relatively minor offenses such as graffiti, turnstile jumping, cannabis possession, and aggressive panhandling by "squeegee men", on the theory that this would send a message that order would be maintained.

Giuliani's entrance led Democratic Congressman Charles Rangel and others to recruit then-First Lady Hillary Clinton to run for Moynihan's seat, hoping she might combat his star power.

[113] In March 2000, however, the New York Police Department's fatal shooting of Patrick Dorismond inflamed Giuliani's strained relations with the city's minority communities,[114] and Clinton seized on it as a major campaign issue.

[114] Then followed four tumultuous weeks in which Giuliani learned he had prostate cancer and needed treatment; his extramarital relationship with Judith Nathan became public and the subject of a media frenzy; and he announced a separation from his wife Donna Hanover.

He made frequent appearances on radio and television on September 11 and afterwards – for example, to indicate that tunnels would be closed as a precautionary measure, and that there was no reason to believe the dispersion of chemical or biological weaponry into the air was a factor in the attack.

[123] When Saudi Prince Alwaleed bin Talal suggested the attacks were an indication that the United States "should re-examine its policies in the Middle East and adopt a more balanced stand toward the Palestinian cause," Giuliani asserted, "There is no moral equivalent for this act.

When suggestions were made that Giuliani's confirmation hearings would be marred by details of his past affairs and scandals, he turned down the offer and instead recommended his friend and former New York Police Commissioner Bernard Kerik.

[165] On May 24, 2006, after missing all the group's meetings,[166] including a briefing from General David Petraeus, former Secretary of State Colin Powell and former Army Chief of Staff Eric Shinseki,[167] Giuliani resigned from the panel, citing "previous time commitments".

[199] Facing declining polls and lost leads in the upcoming large Super Tuesday states,[200][201] including that of his home New York,[202] Giuliani withdrew from the race on January 30, endorsing McCain.

[209] Giuliani also explored hosting a syndicated radio show, and was reported to be in talks with Westwood One about replacing Bill O'Reilly before that position went to Fred Thompson (another unsuccessful 2008 GOP presidential primary candidate).

[213] A November 2008 Siena College poll indicated that although Governor David Paterson – promoted to the office via the Eliot Spitzer prostitution scandal a year before – was popular among New Yorkers, he would have just a slight lead over Giuliani in a hypothetical matchup.

[214] By February 2009, after the prolonged Senate appointment process, a Siena College poll indicated that Paterson was losing popularity among New Yorkers, and showed Giuliani with a fifteen-point lead in the hypothetical contest.

[242] The status of this informal role for Giuliani is unclear because, in November 2018, Trump created the Cybersecurity and Infrastructure Security Agency (CISA), headed by Christopher Krebs as director and Matthew Travis as deputy.

In the weeks following his appointment, Giuliani was forced to consult an Apple Store Genius Bar when he "was locked out of his iPhone because he had forgotten the passcode and entered the wrong one at least 10 times", belying his putative expertise in the field.

[306] On October 2, 2019, Steve Linick, the State Department's inspector general, delivered a 40-page packet of apparent disinformation regarding former vice president Joe Biden and former ambassador to Ukraine, Marie Yovanovitch, to Capitol Hill.

[320] Firtash's attorneys obtained a September 2019 statement[321] from Viktor Shokin, the former Ukrainian prosecutor general who was forced out under pressure from multiple countries and non-governmental organizations, as conveyed to Ukraine by Joe Biden.

Bloomberg News also reported that its sources told them Giuliani's high-profile publicity of the Shokin statement had greatly reduced the chances of the Justice Department dropping the charges against Firtash, as it would appear to be a political quid pro quo.

[351] "Federal prosecutors in Brooklyn have been investigating whether several Ukrainian officials helped orchestrate a wide-ranging plan to meddle in the 2020 presidential campaign, including using Rudolph W. Giuliani to spread their misleading claims about President Biden and tilt the election in Donald J. Trump's favor", the Times reported.

[357] On November 7, Giuliani gave a press conference at Four Seasons Total Landscaping in Philadelphia to discuss challenging the vote count in Pennsylvania, during which media networks called the presidential election for Biden.

[359] This team – a self-described "elite strike force" that included Sidney Powell, Joseph diGenova, Victoria Toensing, and Trump campaign attorney Jenna Ellis [360][361] – appeared at a November 19 press conference in which they made numerous false and unsubstantiated assertions revolving around an international Communist conspiracy, rigged voting machines, and polling place fraud.

[396] He has accused them of "passing around USB ports as if they were vials of heroin or cocaine" and engaging in "surreptitious illegal activity," citing video footage that, according to Moss, actually showed the women with "a ginger mint".

During the trial on the amount of damages, the plaintiffs' testified that Giuliani's false statements, beginning with one of his tweets, prompted a barrage of threatening phone calls and messages against them, including many that were violent, vulgar, or racist.

[432] Two days before that deadline, lawyers Kenneth Caruso and David Labowsky told the judge they did not want to represent Giuliani anymore,[433] and Freeman and Moss learned that the Long Island storage unit contained 20 pallets of moving boxes and furniture.

On November 22, Freeman and Moss told U.S. District Judge Lewis Liman there had been attempts to "intimidate or interfere" with their access to the storage unit and that it was taking the form of a social media campaign against them.

"[515][516][517] Also in September 2023, Hunter Biden filed a civil lawsuit against Giuliani, his companies and attorney Robert Costello, alleging that they had spent years "hacking into, tampering with, manipulating, copying, disseminating, and generally obsessing over data that they were given that was taken or stolen from" his personal devices and caused "total annihilation" of his digital privacy.