Trump has repeatedly sympathized with Hillary Clinton over the Lewinsky affair in the past

In a series of late1999 interviews, the year Hillary Clinton began exploring a run for Senate in New York, Trump expressed sympathy for her for having endured so much.

Trump, who at the time was considering his own run for office as a Reform Party presidential candidate, was often asked about Clinton’s run and how he had praised her just two years earlier in his book Art of the Comeback.

In one October interview, he called independent investigator Ken Starr “crazy” and “a total wacko” and praised Clinton as tough.

“I don’t view it as that,” Trump told Geraldo Rivera on CNBC in November when asked if he thought Clinton was a carpetbagger. “I actually think she’s a very, very nice lady. I— met her a number of times. I met her with my son. She couldn’t have been nicer. I think she’s a very, very good person. I think she’s— had a very tough life the last few years. I mean, what could be tougher than that? I mean, can you imagine those evenings when he’s just being lambasted by this crazy Ken Starr, who is a total wacko? There’s the guy. I mean, he is totally off his rocker. And can you imagine being lambasted like that all day and then saying, ‘Darling, what are we having for dinner?’ It’s got to be pretty tough.”