The remarks are the first time that Trump has raised the former president's alleged affairs and Hillary Clinton's behavior amidst a flurry of accusations since becoming the Republican Party's presumptive nominee. Trump had previously accused Clinton of being an "enabler" to her husband's behavior, but he ramped up his rhetoric on Friday.
"She's been the total enabler. She would go after these women and destroy their lives," Trump said, adding, "She was an unbelievably nasty, mean enabler, and what she did to a lot of those women is disgraceful."
Trump did not expand upon what he believes Clinton did to "destroy" the lives of those women. A message left with the Clinton campaign Friday night was not immediately returned.
The brash billionaire on Friday sought to get ahead of what he believes will be an onslaught of attack ads against him, focusing specifically on sexist remarks he has made.
"So what they're doing is $90 million of ads on Donald Trump and it has to do a lot with the women's issue. But I'm saying to myself, nobody in this country and maybe in the history of this country politically was worse than Bill Clinton with women," Trump said to cheers at a rally here.
Trump predicted the Clinton campaign would use crude comments he has made about women and sex in interviews with talk radio host Howard Stern against him in attack ads.
Trump has used a range of words to describe women he's disagreed with, such as Rosie O'Donnell and Arianna Huffington, including "fat pig," "slob" and "dog."
"Don't forget, I was never going to run for office," Trump said in his defense.
He also retweeted a tweet calling Megyn Kelly a "bimbo" earlier this year, and in the first GOP debate, suggested that Kelly was on her period as the Fox News anchor asked him a prodding question.
And he suggested that then-GOP presidential rival Carly Fiorina was too ugly to be elected last fall: "Look at that face! Would anyone vote for that?" Trump said during an interview with Rolling Stone magazine.
Trump defiantly defended himself Friday: "Nobody respects women more than me."