Of things unlikely to ever be mentioned during a presidential debate, Rosie O'Donnell would be near the top, just ahead of, let's say, Moon Boots. Regardless, Donald Trump said this toward the tail end of Monday's debate: “Rosie O’Donnell, I said very tough things to her, and I think everyone would agree that she deserves it and nobody feels sorry for her." So why did he use valuable debate time to discuss the comedian? Jezebel explains their "seemingly random feud" started with a 2006 episode of The View during which O'Donnell lobbed what would, in 2016, become common attacks on Trump: that his success is due to his father, that he used bankruptcies to get out of paying debts, and that he has a history of failed marriages.
Jezebel argues that because the insults came from a woman, particularly one Trump isn't attracted to, O'Donnell became his "boogeyman." He's gone on to call her fat, ugly, disgusting, and a "true loser" over the years. CBS News reports O'Donnell responded to being called out during a presidential debate, tweeting that the "orange anus ... can't seem to get over" something that happened a decade ago. According to Time, Madonna stood up for her A League of Their Own costar, posting that "cruelty never made anyone a winner" on her Instagram. Strangely, the guest on the 2006 episode of The View that started this whole thing was Hillary Clinton, NBC News reports.