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Donald J. Trump and Bill Clinton used to be golfing buddies and occasional telephone friends. Mr. Trump donated to the former president’s charitable foundation. Mr. Clinton attended the billionaire developer’s lavish third wedding in 2005.

But as Mr. Trump, the Republican presidential candidate who is leading most polls, sets his sights on a potential general election matchup against Hillary Clinton, he is making her husband’s history of marital infidelity a central issue. On Monday, Mr. Trump accused Mr. Clinton of having a “terrible record of women abuse” and warned that he would be a liability to her campaign.

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! — Donald J. Trump (@realDonaldTrump) December 28, 2015

The assault on Mr. Clinton’s character has been couched as a counterpunch. Mrs. Clinton said last week that Mr. Trump had a “penchant for sexism” after he said that she was doing “disgusting” things in the bathroom during the last Democratic presidential debate.

Over the weekend, Mr. Trump said that that Mrs. Clinton was playing the “woman’s card” and that her husband’s sexual history would be fair game as the 2016 race ramped up. “His presidency was really considered to be very troubled, to put it mildly, because of all of the things that’s she talking to me about,” Mr. Trump said Sunday on Fox News.

Mr. Clinton admitted to having an affair with an intern while he was president, and rumors that there were other instances of infidelity have swirled around him for years. His political opponents tried unsuccessfully to have him removed from office, and the issue has largely receded in the ensuing decades.

But Mr. Trump is going there.

In pursuing this line of attack, Mr. Trump appears to be taking a page from the playbook of his former political adviser Roger Stone. Mr. Stone, a veteran Republican strategist who worked for Richard Nixon and Ronald Reagan, published a book earlier this year titled “The Clintons’ War on Women” in which he accuses Mr. Clinton of being a serial philanderer and a rapist whom he compared to the disgraced comedian Bill Cosby.

Although Mr. Stone is no longer officially affiliated with Mr. Trump’s campaign, he has been encouraging the criticism of Mr. Clinton on social media while promoting his book. He accused Mrs. Clinton on Monday of bullying her husband’s sexual assault victims and over the weekend he reposted an old photograph on Twitter of Mr. Clinton and Monica Lewinsky standing together in the White House.

Also on Monday, Ben Carson weighed in on the subject, telling Fox News that Mr. Clinton had a bad influence on children. “You know my main problem with it is that I saw innocent little kids, you know as a pediatric neurosurgeon,” Mr. Carson said, adding: “I see them becoming coarser and wanting to know what certain things are that they’re hearing about on television – things that they would’ve never known about as kids before. And a certain innocence disappears from our society; I’m sorry to see that happen and I’m sorry that it was because one of our presidents.”

The Clintons have publicly moved past their marital problems, and efforts to dredge them up could backfire against Mr. Trump since voters tend to view Mrs. Clinton sympathetically whenever the issue has come up.

Christina Reynolds, a spokeswoman for the Clinton campaign, said in a statement on Monday night that Mrs. Clinton would not be distracted by any “slings” thrown by Mr. Trump at her or her husband. However, she vowed not to let his insults directed at women, immigrants, Muslims and the disabled go unanswered.

“Donald Trump’s words are demeaning, his policies are just as destructive,” Ms. Reynolds said. “Hillary Clinton will continue to stand up to Donald Trump and all the Republicans who try to rip away the progress we have made.”

Mr. Trump has faced his own allegations of mistreating women. Most recently he criticized the appearance of Carly Fiorina, a Republican opponent, and Rosie O’Donnell, a comedian with whom he has publicly feuded. In July, The Daily Beast reported that Mr. Trump’s first wife, Ivana, said in their divorce deposition that he once raped her. She later disavowed that allegation.

Mr. Trump’s strategy of raising the Clintons’ marital problems also represents another about-face for Mr. Trump, who has been friendly with Mr. Clinton over the years and even called him before announcing his presidential bid in May.

In 2008, Mr. Trump suggested during an interview that Mr. Clinton’s infidelity was no big deal.

“Look at the trouble Bill Clinton got into with something that was totally unimportant,” Mr. Trump said on CNN. “And they tried to impeach him, which was nonsense.”

Mr. Clinton has also praised Mr. Trump as recently as September, when he said the Republican had a lot of “pizzazz and zip.”

He was more glowing four years ago even when asked about Mr. Trump’s promotion of the myth that President Obama was not really an American citizen.

“Donald Trump has been uncommonly nice to Hillary and me,” Mr. Clinton said as he dismissed the birther controversy as nonsense. “We’re all New Yorkers. And I love playing golf with him.”