When Bill Clinton's sex scandals were still fresh back in the 1990s, however, Trump took a much different approach to discussing them — expressing sympathy for Hillary Clinton, defending Bill Clinton and dismissing his accusers, and in one interview with Howard Stern, making light of Bill Clinton's infidelity.
Already this election season, Trump has called Bill Clinton the "greatest woman abuser of all time" and pointed the finger at Hillary Clinton for what he has described as enabling her husband's sexual misdeeds and attacking the women who came forward against him.
"She's been the total enabler. She would go after these women and destroy their lives," Trump said
at a campaign rally in May. "She was an unbelievably nasty, mean enabler, and what she did to a lot of those women is disgraceful."
On Sunday, Trump twice retweeted Juanita Broaddrick, the woman who in 1999 at the tail end of his presidency, accused Bill Clinton of raping her in the 1970s when he was the attorney general of Arkansas. Clinton denied the allegations through his lawyers at the time, and no legal proceedings were ever brought against him.
The Trump campaign in late September circulated
talking points telling surrogates to bring up women like Gennifer Flowers and Monica Lewinsky to counter questions about comments Trump made about former beauty queen Alicia Machado.
Speaking with Wolf Blitzer in November 1999 in video reviewed by CNN's KFile, Trump said Hillary Clinton had been through more public controversy than any women should have to bear.
"I think she's gone through terrible times," Trump told Blitzer in the interview. "I think she's been through more than any woman should have to bear — everything public. I mean, women go through this on a private basis and can't take it, she's on the front page of every newspaper every week with what went on in Washington."
A month before, in an interview with CNBC, Trump expressed a similar sentiment about Hillary Clinton and blasted the independent investigator Ken Starr as "a total wacko."
"I think she's a very, very good person," Trump said of Clinton. "I think she's had a very tough life the last few years. I mean, what could be tougher than that? I mean, can you imagine those evenings when he's just being lambasted by this crazy Ken Starr, who is a total wacko? There's the guy. I mean, he is totally off his rocker. And can you imagine being lambasted like that all day and then saying, 'Darling, what are we having for dinner?' It's gotta be pretty tough."
Trump also repeatedly dismissed and at times mocked Bill Clinton's accusers.
In a 2008 interview
with CNN, Trump called the Lewinsky scandal "totally unimportant" and said it was "nonsense" that Republicans tried to impeach him.
In another interview
, with CNBC in 1998 and first unearthed by the Washington Post, Trump called Clinton accuser Paula Jones "a loser." In August 1998, Trump again dismissed Jones, and said Bill Clinton was actually the victim.
"I don't necessarily agree with his victims," Trump said to Fox News' Neil Cavuto in a clip uncovered
earlier in the year by the "Daily Beast." "His victims are terrible. He is, he is really a victim himself. But he put himself in that position."
"These people are just, I don't know, where he met them - where he found them," Trump continued. "But the whole group — it's truly an unattractive cast of characters. Linda Tripp, Lucianne Goldberg, I mean, this woman, I watch her on television. She is so bad. The whole group, Paula Jones, Lewinsky, it's just a really unattractive group. I'm not just talking about physical."
The Trump campaign did not return a request for comment.
As reported on Saturday by CNN's KFile, Trump also joked about Jones's celebrity boxing match in 2002, calling her "not very talented" and saying, "it's too bad she didn't run like that from Bill (Clinton)."
Trump — who now wields Bill Clinton's past misdeeds as a weapon against Hillary Clinton — made light of Clinton's sex life in an interview Howard Stern in 1999, joking that she may have encouraged Bill Clinton to cheat.
"What's gonna happen with Clinton when he retires as a young man of 53 or 54?" Trump asked in the interview.
"He's gonna run a company or something," replied Stern.
"But do you think he'll stay married?" Trump asked.
"I think he will because --," said Stern, before co-host Robin Quivers interjects, "She lets him do whatever he wants."
"He's got the perfect marriage," Stern added.
"Right," responded Trump.
"He does whatever he damn well pleases," said Stern.
"I think she might even encourage him," said Trump.
"Right, I don't think she really wants him on top of her and that's the way it goes," said Stern, to which Trump laughs.