Trump Questions Hillary Clinton's 'Loyalty' to Bill

Arriving nearly two hours late, and a day after vowing he would be "nastier" than his Democratic rival Hillary Clinton, Trump insinuated that she was unfaithful to her husband and "could be crazy." He also reprised a call to jail her — "she should be in prison" — which was followed by a chorus of chants to "lock her up."

The mockery and dark tones came just as a New York Times report was published showing that Trump, who has made his business acumen a cornerstone of his campaign, actually lost nearly $1 billion in failed businesses in a single year. The loss may have allowed him under the law to avoid paying federal income taxes for 18 years following the 1995 filing, the Times reported.

Related: New York Times Publishes Trump '95 Tax Return, Documents Show $916M Loss

Trump did not address the breaking news during his rally here, but instead focused on pushing innuendos he has been hinting at in recent weeks.

Trump said Hillary Clinton's "only loyalty is to her financial contributors and to herself. I don't even think she's loyal to Bill, you wanna know the truth. And really folks really," Trump leveled with a knowing chuckle. "Why should she be, right? Why should she be?"

He reminded minutes later: "Remember: He got impeached for lying. You remember what he lied about. But he got impeached for lying."

The comments come as speculation has swirled about whether Trump would revive attacks on the Clintons' marriage by focusing on Bill Clinton’s past infidelities and casting them as a character flaw of Mrs. Clinton. Throughout the campaign, Trump has dangled the line of attack, starting to integrate it into his rallies over the spring only to pull back as the season changed to summer.

He warned, however, in a Friday night phone interview with the New York Times: ”she’s nasty, but I can be nastier than she ever can be.” He went on to call President Clinton “the single greatest abuser of women in the history of politics” -- an attack he’s lobbed before.

Trump’s attack on the Clintons' marriage comes as he rounds out a week where headlines about his poor treatment of women dominated the news cycle. In a pre-dawn series of tweets on Friday, Trump sought to discredit former Miss Universe Alicia Machado with allegations of a sex tape (that didn't exist) after his past comments about Machado's weight earned scrutiny during the first presidential debate. Trump himself, with his tweets and comments in interviews, added the fuel that allowed the story to build throughout the week.

The Republican nominee also once again went after Clinton for her health, going so far as to physically mock her for a video that appeared to show Clinton stumbling to her car leaving a 9/11 memorial service in downtown Manhattan last month.

"Here's a woman, she's supposed to fight all of these different things and she can't make it 15 feet to her car. Give me a break. Give me a break," Trump said, wobbling in front of his podium to indicate Clinton walking to the car.

This is the second time Trump has attacked Clinton for the moment, which resulted in the Clinton campaign telling reporters that Clinton had been diagnosed with pneumonia days earlier.

Taking the attacks a step further, Trump posited that Clinton "could be crazy. She could actually be crazy." He repeatedly called her a "disaster."

The words fit a pattern for Trump when it comes to how he speaks about women. While he frequently calls out rivals of both sexes, Trump often seeks to discredit women by attacking their mental capacity or physical appearance. A well worn and long used knock on Hillary Clinton is that she lacks the "strength and stamina" to be president and that she doesn't "look" presidential.