That Trump's campaign started zeroing in on Clinton's history with women may not come as a shock; Trump has been hinting at the former president's past on the campaign trail, and one of his best-known confidants has been doing so for years.
Roger Stone, a close friend and sometime adviser of Trump's, co-authored a book called "The Clintons' War on Women," which was published in October.
Trump called Clinton "the worst abuser of women" in an interview with CNN earlier this month and used a similar line during a campaign speech in Spokane, Washington.
"Hillary was an enabler, and she treated these women horribly. Just remember this, and some of those women were destroyed not by him but by the way that Hillary Clinton treated them after everything went down," Trump said in the Spokane speech.
For her part, Hillary Clinton is avoiding engaging in the back-and-forth. During an interview with CNN in Illinois last week, she was asked if she felt compelled to defend her husband's honor or their relationship. "Not at all," she said. "I know that that's exactly what he is fishing for, and you know, I'm not going to be responding."
Trump's Latest Attack
In the new campaign video released Monday on Instagram, audio of three women's voices can be heard while a picture of the former president is shown over the White House.
Trump did not name the women in the video, but all the recordings used had been publicly released.
The first recording is of Lewinsky, the White House intern who was at the center of the scandal that resulted in Bill Clinton's impeachment and eventual acquittal.
The second is of Kathleen Willey, a former White House volunteer who made accusations against Bill Clinton, and the third is of Juanita Broaddrick, an Arkansas resident who claimed Bill Clinton assaulted her when he was the state's attorney general.
Trump has said he thinks it's necessary to go negative with his campaign.
"I don't like doing that," he said of the Instagram video, "but I have no choice when she hits me on things. I just have no choice, so you have to do it. It's unfair."
Trump, speaking to Fox News' Bill O'Reilly on Monday, said of the Clintons, "You know, they're dirty players, they've been dirty players historically, and I have to fight back the way I have to fight back."
Vince Foster Suicide
Trump also raised questions about the suicide of a Clinton family confidant, deputy White House counsel Vince Foster, who was found dead in what was ruled a suicide in 1993.
Trump was asked about Foster's death in an interview with The Washington Post that took place last week but was not publicly shared until Monday. He brought up decades-old conspiracy theories among some on the far right and far left, calling Foster's death "very fishy."
"He had intimate knowledge of what was going on. He knew everything that was going on, and then all of a sudden he committed suicide," Trump said, adding, "I don't bring [Foster's death] up because I don't know enough to really discuss it."
Foster's death was ruled a suicide by multiple investigations, including ones conducted by the FBI, the Department of Justice and the United States Park Police. Whitewater independent counsel Kenneth Starr issued a 114-page report in 1997 confirming the outcome of the earlier investigations.
Hillary Clinton's team has not directly responded to the specific claims and has refused to engage Trump on the allegations.
"I think it's bad strategy," Hillary Clinton's campaign spokesman Brian Fallon told Bloomberg on Monday, adding that "it was two decades ago."
Claims by Juanita Broaddrick
Trump has made other efforts to smear his likely general-election opponent. Trump brought up Broaddrick during an interview with Fox News' Sean Hannity, classifying her claims as "rape."
Broaddrick is heard in the Instagram video saying, "He starts to bite on my top lip as I tried to pull away from him."
That recording is from a 1999 interview she did with "Dateline NBC" in which she detailed what she said happened between her and Bill Clinton in a hotel room in Little Rock, Arkansas, in 1978. Broaddrick denied those allegations in a 1998 lawsuit but recanted her denial in 1999.
No criminal charges were ever filed in the case, and Bill Clinton's personal lawyer said her claims were "absolutely false" in 1999 when they were made public.
Kathleen Willey's Claims
Willey was a volunteer at the White House in November 1993 when, she alleged, Bill Clinton assaulted her in the Oval Office. She said he kissed and fondled her. She first publicly disclosed her claims on "60 Minutes" in 1998 during the Lewinsky scandal. In 2007, when Hillary Clinton was first running for president, Willey released a book titled "Target: Caught in the Crosshairs of Bill and Hillary Clinton," and she went on Fox News to promote the book.
"No woman should be subjected to it. It was an assault," she said during that interview, the audio of which was repurposed by Trump in his Instagram video.
During the impeachment proceedings, which started in late 1998, Bill Clinton denied ever assaulting Willey. "When she came to see me, she was clearly upset. I did to her what I have done to scores and scores of men and women who have worked for me or been my friends over the years. I embraced her, I put my arms around her, I may have even kissed her on the forehead. There was nothing sexual about it," he said in his testimony.
The U.S. Office of the Independent Counsel had concerns about the veracity of Willey's statements because she had lied to the FBI, and in the office's final report, it said that there was insufficient evidence to think his testimony was false.
The Paula Jones Lawsuit
In 1994, Paula Jones filed a sexual harassment lawsuit against Bill Clinton, claiming that in 1991, when he was Arkansas' governor and she was working at a hotel in Little Rock, he propositioned her at a room in the hotel. The case went on for four years and was settled when he agreed to pay her $850,000 to drop the case.
When the agreement was announced, Bill Clinton's attorney Bob Bennett said in a statement, "The president remains certain that the plaintiff's claims are baseless" and "has decided he is not prepared to spend one more hour on this matter." The deal did not include an apology.
"Nothing in this agreement shall be construed to be an admission of liability or wrongdoing by any party," read the agreement.