 Donald Trump and Rosie O’Donnell have long been embroiled in a heated feud, but following the Republican nominee’s renewed criticism of O’Donnell during Monday’s first presidential debate, Madonna came to the defense of her former costar. — Seth MacFarlane (@SethMacFarlane) September 27, 2016 
 
 ROSIE O'DONNELL WAS JUST NAME CHECKED DURING A DEBATE TO DECIDE THE LEADER OF THE MOST POWERFUL COUNTRY IN THE WORLD — John DeVore (@JohnDeVore) September 27, 2016 
 
 “Rosie O’Donnell — I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her,” Trump said. Left the first wife, had an affair, left the second wife, had an affair, had kids both times but he’s the moral compass for 20-year-olds in America.” 
 
 A decade ago, as NBC points out, O’Donnell helped to mainstream a now-popular line of attack against Trump—that he’s not self-made but a product of his father, that he repeatedly bankrupted himself to get out of paying what he owed, that he’s a “snake-oil salesman.” 
 
 Advertisement 
 
 Trump didn’t take this so well, and has since referred to O’Donnell as “a woman out of control,” a “true loser,” a “total train wreck,” “disgusting,” a “slob,” “fat, ugly”; he told Entertainment Tonight in 2006: “Probably I’ll sue her, it’ll be fun. Rosie O’Donnell has never been one to take Donald Trump’s insults sitting down, and the TV personality is standing up for herself after the presidential candidate name-checked her during Monday’s debate.
– 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.