For weeks, Donald Trump has dredged up stories from the 1990s about Bill Clinton's extramarital affairs. Then Trump went a step further, reviving an unsubstantiated rape accusation against the former president.
Even for Trump, the anything-goes showman whose insults left rivals reeling in the GOP primaries, the attacks have a searing personal dimension, pushing boundaries and forcing his presumed Democratic rival, Hillary Clinton, to relive the humiliation of her husband's adultery.
Given Trump's own extramarital dalliances along his tabloid-chronicled path from his first wife to his second and third, the tactic could backfire. But it serves strategic goals for the presumptive GOP presidential nominee.
His almost daily reminders of Clinton melodramas darken the glow that the former first couple often put on their White House years, an era of economic prosperity.
Trump is open about also using the personal attacks to blunt attempts by Hillary Clinton and her allies to go after him over his repeated derogatory remarks about women, including crude assessments of sex appeal.
Charlie Black, a veteran GOP campaign consultant who supports Trump, said Bill Clinton's history is fair game when Trump is fighting the Democrats' accusations.
"A lot of voters are so young they don't even know about this stuff," Black said. "And the ones who are old enough to remember, it probably doesn't hurt to remind them of it — that [Hillary Clinton's] cooperation with him in trying to cover up these things is just not a pro-women stance."
Still, there is additional risk in revisiting the tumultuous past: Reminding voters of the GOP's hypocrisy in the White House sex scandal.
Newt Gingrich, the House speaker who led the charge for Clinton's 1998 impeachment, admitted later that he was having an extramarital affair at the time.
Gingrich's designated successor, Rep. Bob Livingston of Louisiana, gave up the post just before Clinton's Senate trial after acknowledging his own extramarital affairs. Republicans then gave the speaker's job to Rep. J. Dennis Hastert of Illinois, who was sentenced last month to 15 months in prison for trying to cover up his sexual abuse of high school boys on a wrestling team that he coached.
As noted by Paul Begala, a senior White House advisor to Bill Clinton and one of his most pugnacious defenders, the result was a backlash that resulted in a surprising gain of Democratic seats in the 1998 congressional election.
"It didn't work when it was hot and new, and about the guy that was president," said Begala, now a strategist for a pro-Hillary Clinton political action committee. "I don't think it's going to work when it's old and stale and about the husband of the woman running for president."
Trump's frequent bragging about his sexual conquests, along with his affair with second wife Marla Maples when he was still married to Ivana Trump, make his attacks on Bill Clinton awkward.
"If I told the real stories of my experiences with women, often seemingly very happily married and important women, this book would be a guaranteed best-seller," he wrote in "The Art of the Comeback."
In a deposition taken during their divorce proceedings in the 1980s, Ivana Trump alleged that Trump had once raped her. When it became public in 1993, she issued a statement saying that once in 1989, the couple "had marital relations in which he behaved very differently toward me than he had during our marriage."
"As a woman, I felt violated, as the love and tenderness, which he normally exhibited towards me, was absent," she said. "I referred to this as a 'rape,' but I do not want my words to be interpreted in a literal or criminal sense."
For weeks, Trump has made a point of bringing up Bill Clinton's sexual history each time his wife or her allies accuse the New York mogul of mistreating women.
At a recent rally in Oregon, Trump — offering no evidence — called Clinton "an unbelievably nasty, mean enabler" of her husband's misconduct. "So put that in her bonnet, and let's see what happens, OK?" he said.
Trump has good reason to fight back: 60% of women view him unfavorably, a New York Times-CBS News poll found last week. That Clinton is almost as unpopular among men — 58% of them hold an unfavorable opinion of her — makes it no less important for him to improve his standing among women.
On Thursday, Trump intensified the attacks. He reminded Fox News viewers that Bill Clinton's law license was suspended for five years when he left office in 2001 in a deal to avoid prosecution for making false statements about his affair with former White House intern Monica Lewinsky.
Trump brought up what he called Clinton's "impeachment for lying" (the Senate acquitted him) and "massive settlements," an apparent reference to the $850,000 Clinton agreed to pay Paula Jones to resolve her claim that he sexually harassed her in 1991.
Most striking, Trump repeated former campaign intern Juanita Broaddrick's 1999 allegation that Clinton had raped her in 1978, a case that was never adjudicated because she waited 21 years before making the accusation.
In good part, the volatile celebrity businessman appears to be trying to rattle the Clintons — so far, to no avail.
"I have very thick skin," Hillary Clinton told CNN on Thursday.
"Do you ever feel compelled to defend your honor, the honor of your husband?" reporter Chris Cuomo asked.
"No," she said.
"With statements he's making that go to the core of the relationship?"
"No, not at all," Clinton said. "I know that that's exactly what he is fishing for, and you know I'm not going to be responding."
Bill Clinton, whose red-faced, finger-wagging lectures have caused trouble for his wife's campaigns in the past, was equally measured last week when asked for comment at an appearance in Puerto Rico.
"I think people are smart enough to figure this out without my help," he said.
Hillary Clinton has elevated her husband as a target by giving him a prominent role in her campaign. Stumping in Kentucky last week, she said she would put the former president in charge of revitalizing the economy if she wins the White House, which raised his import even more.
On Friday, Trump joked that Hillary Clinton wants her husband to oversee economics to keep him from tomcatting.
Charlie Cook, one of Washington's leading nonpartisan election handicappers, suggested Clinton might be better off playing down her husband's presidency and minimizing any part that he might play in hers.
"The country did very well under President Clinton, but it was an eight-year soap opera that I'm not sure people are in the mood to revisit," he said.
The latest volleys from Trump came after Begala's super PAC, Priorities Action USA, started airing ads on May 16 in the battleground states of Ohio, Florida, Nevada and Virginia. They feature Trump remarks that many women found offensive. Among them: "A person that is flat-chested is very hard to be a 10."
Garry South, a California Democratic strategist known for provocative campaign tactics, said Trump's aggressive response seemed designed to knock the Clintons off stride by goading them in a deeply personal way.
"I think it's a huge risk," South said. "I don't think women are going to take well to this, particularly from a self-confessed philanderer who's been married three times and had children from three different marriages."