As it turns out, with another young beauty queen.

In 2006, 20-year-old Tara Conner won the Miss USA pageant, a franchise of which Mr. Trump was a co-owner, but she soon found herself under fire because of tabloid reports that she was drinking, using drugs and had been seen kissing a woman.

Mr. Trump was not pleased. Ms. Conner faced the prospect of losing her crown until he relented, publicly forgiving her in a televised news conference at Trump Tower. “I’ve always been a believer in second chances,” he said.

That is where Rosie O’Donnell came into the picture. Ms. O’Donnell was then a co-host on “The View,” and she used her seat around the show’s signature table to criticize Mr. Trump (who at the time had been divorced twice after accusations of marital infidelity) as a hypocrite for his showy display of public forgiveness.

Ms. O’Donnell mocked his haircut, tousling her hair to mimic a comb-over, and put on a cartoonish Queens accent. She criticized his many bankruptcies and his record of not paying contractors who had done work for him. She said he was like a snake-oil salesman.