For years, President Bill Clinton was the best friend Donald J. Trump always hoped to have.
When scandal engulfed Mr. Clinton’s White House, Mr. Trump leapt to the president’s defense. “He’s probably got the toughest skin I’ve ever seen, and I think he’s a terrific guy,” Mr. Trump told CNN.
Then there were Mr. Trump’s pitches to the former president to settle in a gilded Trump building in Manhattan when he and Hillary Clinton left the White House. They moved to Westchester instead. His overtures for them to vacation at his Mar-a-Lago estate in Palm Beach, Fla., were also rebuffed. The Clintons preferred the Dominican Republic.
When Mr. Clinton had trouble joining a conservative Westchester golf club, Mr. Trump boasted that he welcomed the former president to a newly built Trump National Golf Club, a five-minute drive from the Clintons’ Chappaqua, N.Y., home.
“He’s a great gentleman, a good golfer and a wonderful guy,” the real estate developer said of Mr. Clinton, who, in reality, is a so-so golfer known for taking mulligans.
In the past week, any semblance of a friendship between Mr. Trump and Bill Clinton came to an ugly end as the former president and his wife’s presidential campaign found themselves in a muddy battle over sexism with the Republican candidate who has upended this election cycle with his insults and attacks.
“If Hillary thinks she can unleash her husband, with his terrible record of women abuse, while playing the women’s card on me, she’s wrong!” Mr. Trump wrote on Twitter on Monday.
The criticism of Mr. Clinton’s personal life comes as Mrs. Clinton is increasingly relying on the former president, mentioning him in almost every speech as she praises his economic record. But Mr. Trump’s attacks on him are now rippling through the race, with other candidates and even a prominent newspaper columnist suggesting that Mr. Clinton’s sexual history is fair game.
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“This works for Trump because it reinforces what his most ardent supporters believe to be his greatest strength,” said Kevin Madden, a Republican communications strategist. “He will say things that no one else will say but that need to be said.”
On Monday, Mr. Clinton will hold two organizing events for Mrs. Clinton in New Hampshire — his first solo outing on the campaign trail in a state where he remains widely popular and where polls show Mrs. Clinton slightly trailing Senator Bernie Sanders of Vermont.
Mr. Trump’s turn against the former president started last week when Mrs. Clinton, in response to Mr. Trump’s use of a crude sexual reference to describe her loss to Barack Obama in 2008, accused him of having a “penchant for sexism.”
On Saturday, Mr. Trump said on Twitter: “Hillary Clinton has announced that she is letting her husband out to campaign but HE’S DEMONSTRATED A PENCHANT FOR SEXISM, so inappropriate!”
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He went further on Tuesday, saying that in Mr. Clinton’s political career, “there were certainly a lot of abuse of women, and you look at whether it’s Monica Lewinsky or Paula Jones or many of them.”
In response to Mr. Trump’s latest onslaught, Mrs. Clinton’s campaign said in a statement that “Hillary Clinton won’t be bullied” or “distracted by the slings he throws at her and former President Clinton.” A spokesman for Mr. Clinton declined to comment.
Mr. Trump’s tactics could backfire. Mrs. Clinton had some of her highest approval ratings ever after revelations that Mr. Clinton had a relationship with Ms. Lewinsky, a 22-year-old White House intern.
This month at a New Hampshire town hall, a young woman asked Mrs. Clinton about several women who alleged they were sexually harassed by Mr. Clinton.
“You say that all rape victims should be believed,” the woman said. “Should we believe them as well?”
Mrs. Clinton did not hesitate. “Well, I would say that everybody should be believed at first until they are disbelieved based on evidence,” she said, with an awkward smile, as the crowd applauded.
Still, the issue seems to be echoing, at least among her detractors. Other Republican candidates, including Carly Fiorina and Ben Carson, have followed Mr. Trump’s lead, saying Mr. Clinton’s history is a legitimate criticism, though Mrs. Fiorina said she doubted voters would care. Mr. Clinton, after all, is 69 years old, and the Lewinsky scandal happened nearly two decades ago.
The Washington Post columnist Ruth Marcus has been critical of Mr. Trump but on Tuesday wrote that she agreed with him that Mr. Clinton’s past is relevant to his wife’s campaign. “Trump has smeared women because of their looks,” she wrote. “Clinton has preyed on them.”
Mr. Trump has been the most direct in his attacks on Mr. Clinton, but Republicans, concerned about the party’s declining appeal to women, have long considered using the former president’s personal life and Mrs. Clinton’s response to the women who alleged extramarital affairs.
Stuart Stevens, a Republican operative and Mitt Romney’s chief strategist in his 2012 presidential campaign, said the way the Clinton operation disparaged women who complained about the president’s behavior in the 1990s “would be all but disqualifying in a Democratic primary” nowadays.
During Mr. Clinton’s 1992 campaign, Betsey Wright, a close aide, coined the term “bimbo eruptions” in describing rumors of extramarital affairs involving the candidate. According to White House-era documents from Diane D. Blair, a close friend of Mrs. Clinton’s who died in 2000, the first lady had referred to Ms. Lewinsky as “a narcissistic loony toon.”
Until last week, Mr. Trump had hardly uttered a negative word about Mr. Clinton. In 1999, he said the president had been treated unfairly for his relationship with Ms. Lewinsky. His criticism, according to an interview with The New York Times at the time, was the president’s choice of paramour: “It was Monica! I mean, terrible choice.”
Mr. Trump has been a donor to the Bill, Hillary & Chelsea Clinton Foundation and to Mrs. Clinton’s Senate campaign. While a senator from New York, Mrs. Clinton and her husband attended Mr. Trump’s 2005 wedding to his third wife, the Slovenian model Melania Knauss, held in a $42 million ballroom at his Mar-a-Lago estate decorated to resemble Versailles. (Mr. and Mrs. Trump were not invited to Chelsea Clinton’s 2010 wedding.)
“He liked them and their star quality, and he respected a lot of things Bill Clinton did as president,” said Edward G. Rendell, a former governor of Pennsylvania who is close to the Clintons. “That’s all out the window now,” he added.
In an email, Mr. Trump said his friendship with Mr. Clinton was strictly business. “It was my obligation to get along with all politicians,” he wrote. “And I did it better than anybody.”
He said he did not recall whether the Clintons had stayed at Mar-a-Lago in Palm Beach. “If they did want to stay there, or stayed there, it only shows that they have good taste,” he added.
Some have suggested that Mr. Trump, whose own affair with Marla Maples and his split from his first wife, Ivana Trump, were splashed across tabloids, is an imperfect messenger on the issue of fidelity.
Mr. Trump also opens himself up to criticism about his own personal life, including allegations that he assaulted Ivana Trump, which he has denied and which the former Mrs. Trump recently backed away from.
Mr. Trump, however, said he was “the perfect messenger because I fully understand life and all its wrinkles,” and reiterated his claim that Mrs. Clinton had bullied some of the women who accused her husband of improprieties.
Republican opponents have highlighted Mr. Trump’s previously fawning comments about Mr. Clinton. Back in 1999, Mr. Trump expressed admiration for Mr. Clinton’s retail political skills, telling CNBC: “I wish I could be like that. I just can’t.”
And a couple of years later, he echoed that comment, recalling an anecdote about watching Mr. Clinton work a crowd.
“He shook hands with everybody out there,” said Mr. Trump, who is regarded as something of a germaphobe. “And some of these people had filthy hands.”
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