The hat is a reference to the original family name of Donald Trump, with whom O’Donnell has been in an ugly public feud for years. It started nearly a decade ago when she called him a “snake oil salesman” and mocked his hairdo on The View.
He then called her ugly, fat and stupid several times. He said to Larry King on CNN: ‘She’s an extremely unattractive person who doesn’t understand the truth. … I think she’s a terrible person … She has failed at everything she has done… She’s a bully and she sucker punches people.”
During the first Republican debate, when Fox news anchor Megan Kelly asked Trump about his history of attacking women’s appearances, he replied, “Only Rosie O’Donnell.” To which she replied: “For the record, it was well beyond Rosie O’Donnell.”
O’Donnell has said that Trump’s insults were traumatic for her: “Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child,” she told People Magazine. “It was national, and it was sanctioned societally. Whether I deserved it is up to your own interpretation.”
Believe it or not, O’Donnell attended Trump’s 1993 wedding to his Marla Maples, the second of his three wives.