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From Miss Universe to Monica Lewinsky, Trump Flirts With A Risky Line Of Attack

Donald Trump walks off of the stage after speaking at a rally Friday in Michigan.

If Donald Trump dredges up former President Bill Clinton's history of extramarital affairs to use it against his Democratic rival, it could be a risky move the GOP nominee amid the new storm he stoked over his own comments about and treatment of women.

In his first debate on Monday against Hillary Clinton, Trump boasted that he had valiantly stayed away from the topic despite an inner dialogue with himself about whether to bring up the Clintons' marital woes. Before the debate, he had floated inviting Gennifer Flowers, who allegedly had an affair with the former president in the 1970s, to the event.

"I was going to say something extremely rough to Hillary, to her family, and I said to myself, 'I can't do it. I just can't do it. It's inappropriate — it's not nice,'" Trump said.

But days later, as he faces fallout from a poor performance, Trump and his surrogates have begun to reverse that decision.

In an interview with the New York Times posted Friday night, Trump was the most direct he's been yet in talking about the 1990s scandals. "She's nasty, but I can be nastier than she ever can be," Trump said.

"Hillary Clinton was married to the single greatest abuser of women in the history of politics," Trump continued, referred to the former president who left office with high approval ratings. "Hillary was an enabler, and she attacked the women who Bill Clinton mistreated afterward. I think it's a serious problem for them, and it's something that I'm considering talking about more in the near future."

Trump's direct comments came after aides had only begun to hint at the strategy. After Monday's debate, former New York Mayor Rudy Giuliani said Trump was too "gentlemanly" to say what he'd have said about the former first lady's handling of her husband's affair with a White House intern.

"I sure would have talked about what she did to Monica Lewinsky - what that woman standing there did to Monica Lewinsky, trying to paint her as an insane young woman," Giuliani said.

Giuliani added that if Clinton didn't understand what her husband had been up to, she's "too stupid to be president."

The day after the debate, Trump said on Fox News that he was tempted to bring the issue up, after Clinton attacked him for his past comments about former Miss Universe Alicia Machado's weight.

"I didn't feel comfortable doing it. I think I did the right thing. It's not worth a point," Trump said.

Trump campaign manager Kellyanne Conway said on ABC's "The View" that she didn't think Trump got enough credit for his "restraint" during the debate, and criticized Clinton for often questioning the veracity of women, including Lewinsky.

"I'm not advising him to go there. It's fair game to think about how Hillary Clinton treated those women after the fact," Conway said.

In Bedford, N.H., on Thursday, Trump railed against the Clintons' scandals, and seemed to tiptoe in the direction of bringing up the former president's infidelity.

"The Clintons are the sordid past; we will be the very bright and clean future," Trump promised.

Trump, of course, has his own less-than-pristine past; as a New York real estate developer, he often courted tabloid coverage of his personal life, including his two messy divorces and his own extramarital philandering. That may be why Trump was dismissive of the Lewinsky affair on CNN in 2008.

"Look at the trouble Bill Clinton got into with something that was totally unimportant and they tried to impeach him, which was nonsense," Trump said just eight years ago.

In the interview with the Times, Trump even argued that infidelity had "never a problem" for him during his three marriages, despite well-documented evidence to the contrary during his first divorce from Ivana Trump and subsequent marriage to Marla Maples, his second wife.

"I don't talk about it," the GOP nominee said about his own affair with Maples. "I wasn't president of the United States. I don't talk about it. When you think of the fact that he was impeached, the country was in turmoil, turmoil, absolute turmoil. He lied with Monica Lewinsky and paid a massive penalty."

Good or bad, the billionaire real estate mogul has often used his own publicity to his benefit. But on Friday, a series of early-morning tweets, where he once again went on the attack against Clinton and Machado, put the spotlight back on his own treatment of women — and not in a good way.

The GOP nominee tried defend himself against allegations that he'd mistreated the former Miss Universe because of her looks, but also falsely claimed she had been part of a "sex tape."

His comments on Twitter came two days after Trump had told Fox News' Bill O'Reilly that he'd saved Machado's job when the Miss Universe organization wanted to fire her for gaining weight.

Republican strategist Katie Packer, who focuses on how the GOP can reach women, said Trump is saying all the wrong things to try and bridge the gender gap he's facing in November.

"Because they feel like no woman should be punished in her professional life for the actions of her husband," Packer said. "So it's really a bad strategic move for Trump - and I would caution any other Republican out there, certainly any Republican that's on the ballot, to avoid those talking points that are coming from the Trump campaign and to steer clear of this – because it's a losing strategic scenario for Republicans."

Trump's rhetoric is troubling even for some of his supporters, like Michelle Burgess, who came to the rally in New Hampshire. Burgess says she's not personally offended by Trump's remarks, but she knows many women are.

"I mean, it's just raw. I think women want to be accepted for who they are," Burgess said.

The way Trump talks about women in the next few weeks – including his Democratic rival – may determine whether many female voters can accept him.

His campaign seemed to try and repair some of that damage, releasing an ad Friday evening with one of his most effective surrogates — his daughter Ivanka talking about her father's maternity leave plan.

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