In late April and May 2000, Giuliani's medical, romantic, marital, and political lives all collided in a tumultuous four-week period, culminating in his withdrawal from the race on May 19.

Late in 1998, prominent Democratic politicians and advisors, including U.S. Representative Charles Rangel,[6] urged First Lady Hillary Rodham Clinton to run for the U.S. Senate seat.

[8] On July 7, 1999, Clinton formally announced an exploratory committee for the Senate run;[9] the setting was Moynihan's farm in Pindars Corners, in rural Delaware County.

[15] Even the commonplace activity of house hunting leading up to this was the subject of considerable media attention; coverage of personal lives would be the norm in this contest of two "electrifying and polarizing figures" (as one reporter put it).

[23] In her 2003 autobiography, she said that putting on the hat had been a "bad move", but reiterated what had been reported in the press prior to the incident, that she had been "a die-hard Mickey Mantle fan;"[24] the book included a photograph of her with a Yankees cap on from 1992.

"[13] She discussed local issues such as price supports for the dairy industry, fares for air travel, college tuition levels, and the brain drain in parts of the state.

"[37] Giuliani's campaign prepared a 315-page opposition research dossier that went back to her time at Wellesley College; it included eleven pages of what they termed "Stupid Actions and Remarks".

[38][39] By late December 1999, Clinton adapted to Giuliani's psychological warfare, saying in response to one such gambit, "I can't be responding every time the mayor gets angry.

"[37] A February 2000 attempt by Giuliani to capitalize on a Clinton campaign event's accidental playing of Billy Joel's suburban drug tale "Captain Jack"[40] led to more ridicule for him than for her.

[41] Giuliani was on stage in male disco garb spoofing John Travolta in Saturday Night Fever, but also appeared in drag in taped video clips that reworked the "Rudy/Rudia" theme of a past Inner Circle dinner,[42] as well as in an exchange with Joan Rivers that sought to make fun of Clinton.

[43] The New York Police Department's fatal shooting of Patrick Dorismond on March 15, 2000, inflamed Giuliani's already strained relations with the city's minority communities,[33] and Clinton seized on it as a major campaign issue.

[37] Some Giuliani aides and national Republican figures concluded that his interest in the campaign was flagging, as although he was desirous of winning in political combat against a Clinton, he was by nature an executive personality and the prospect of serving as one of a hundred legislators was unappealing to him.

[33][45] In retrospect, The New York Times would write that the battle so far between the two had comprised "a blistering year of mental gamesmanship, piercing attacks, contrasts in personalities and positions, and blunders played out by two outsize political figures in a super-heated atmosphere.

[48] By March 2000, Giuliani had stopped wearing his wedding ring[46] and was being seen more in the company of this other woman, including at the Inner Circle press dinner, the St. Patrick's Day parade, and town hall meetings, but it was not yet fully clear whether the relationship was personal or professional.

[49] On April 26, television channel NY1 reported that Giuliani had undergone a second round of tests for prostate cancer at Mount Sinai Medical Center;[54] the same disease had led to the death of his father.

[58] On May 3 the New York Post finally published its photographs of Giuliani and the woman, now identified as Judith Nathan,[58] leaving a restaurant together,[46][59] under the front-page headline "Rudy's Mystery Brunch Pal is Upper East Side Divorcée".

[53][61]) Later that day, Giuliani responded to a barrage of questions on the subject at a news conference by acknowledging Judith Nathan publicly for the first time, calling her "a very good friend" and expressing his annoyance that her privacy was being invaded.

[53] On May 6 Hanover held an unusually-located news conference at the back of St. Patrick's Cathedral before the funeral of Cardinal John O'Connor;[50] visibly trembling, she said, "I will be supportive of Rudy in his fight against his illness, as this marriage and this man have been very precious to me.

[62] On May 10, Giuliani held what The New York Times described as an "extraordinary, emotional news conference" in Bryant Park to announce that he was seeking a separation from Hanover,[59] saying, "This is very, very painful.

"[67] Clinton, meanwhile, said as little as possible about the situation, preferring to let Giuliani's drama play out on its own;[68] on May 17, as he huddled with his doctors over whether to choose surgery or radiation as his treatment[69] while facing conflicting political advice from his aides,[70] she won the unanimous approval of delegates to the Democratic Party state convention at the Pepsi Arena in Albany, giving a constrained acceptance speech because she did not know her general election opponent.

[91] In media interviews, Fray and his wife acknowledged several factors that tended to undermine his credibility: he had lost his license to practice law for altering court records; he had made false accusations against the Clintons in the past; and he had suffered a brain hemorrhage with some resultant losses of memory.

[95] Talk radio hammered on this, with New York-based Sean Hannity issuing a daily mantra, "Name me three things Hillary Clinton has ever done for the people of New York!"

[103] This issue caused former New York Mayor Ed Koch to take out ads telling Lazio to "stop with the sleaze already,"[102] and did not change the dynamic of the race.

[103][114] Clinton won the traditionally Democratic base of New York City by large margins, and carried suburban Westchester County, but lost heavily populated Long Island, part of which Lazio represented in Congress.

Following his defeat, which set a record for the most money spent in a losing Senate effort,[83] he took positions in the corporate world and avoided electoral politics until becoming a candidate in New York's 2010 gubernatorial election.

[121] When Caroline Kennedy announced her interest in the vacancy, comparisons were drawn to Clinton in 2000, with both being famous people seeking to hold elective office for the first time.

[129] As The Washington Post wrote, "Rudy Giuliani is finally running the race against Hillary Clinton that he first contemplated some 17 years ago: a brutish bout under a white-hot spotlight.

"[129] His actions on behalf of Trump included not only fiery attacks on Clinton's record as Secretary of State but also charges that she was experiencing significant problems with her health.

The attacks continued; in March 2018 Giuliani made a joke at a fundraiser at Trump's Mar-a-Lago resort, the premise of which was that Clinton was almost too fat to fit through doorways.

[141] Giuliani became even more in the public spotlight as a central figure in the Trump–Ukraine scandal and the attempts to overturn the 2020 United States presidential election, and then as the subject of a federal investigation about possible wrongdoing regarding his actions in Ukraine.