Rosie O'Donnell and Donald Trump Have Despised Each Other for Years — What Happened?

Comedian Rosie O'Donnell has worn many hats throughout her career, which spans multiple decades. She started out as a standup comic and after an impressive run on Star Search, shifted into television with a role on the NBC sitcom Gimme a Break!. And while that was only the beginning of her television career, Rosie's life was forever changed by a pivotal role in the film A League of Their Own.

This would lead to her own talk show and eventually The View, where she stayed for just one season. Rosie had her own magazine, her own talk show, and to this day continues to pop in and out of television. Her career has also been marked with some controversy, including a famous feud she has with former President Donald Trump. What happened to Rosie O'Donnell? Let's get into it.

Donald Trump has been mad at Rosie O'Donnell for over a decade. Believe it or not, it all began with the 2006 Miss USA Pageant. As a reminder, Trump owned the Miss Universe Organization from 1996 to 2015. Tara Conner, the 2006 Miss USA winner, was a good girl from Kentucky who finally made it to the big city. When she got to New York, Tara let her hair down and partied it up the way any 20-year-old would do. This involved drinking and entertaining the occasional gentleman caller.

Unfortunately, this kind of behavior was frowned upon by the Miss Universe Organization and Trump in particular. According to People Magazine, Tara entered into rehab in December 2006 after Trump opted to let Tara keep her crown. In a press conference that aired right before The View, Trump said, "I've always been a believer in second chances. Tara is a good person. Tara has tried hard. Tara is going to be given a second chance."

Immediately following this was a live episode of The View where Rosie decided to comment on Trump's press conference. While retelling the story to Seth Meyers in 2017 while on Late Night with Seth Meyers, she said "What is he the pimp, and she's the prostitute?" She then hilariously added, "Who is he? Is he the moral arbiter of 20-year-old behavior?"

Rosie then took the time to point out a few facts about Donald Trump. Specifically, she mentioned that he has filed for bankruptcy four times after being bankrolled by his father. She also brought up the fact that he "Notoriously cheats private contractors out of their money." What did he do? "He went bats--t crazy," responded Rosie.

Mere hours after the episode of The View aired Trump spoke with People Magazine about Rosie O'Donell. "You can’t make false statements," he told the outlet. "Rosie will rue the words she said. I’ll most likely sue her for making those false statements – and it’ll be fun. Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie."

Nearly ten years later, their feud was inexplicably revived when Trump insulted Rosie during the GOP debate in August 2015. Moderator Megyn Kelly said, "You've called women fat pigs, dogs, slobs, disgusting animals. Your Twitter account has several --" At this point Trump interrupted Megyn by saying, "Only Rosie O'Donnell."

He repeated this joke during the first presidential debate when Hillary said, "This is a man who has called women pigs, slobs and dogs." To which he replied, "Some of it I said in entertainment, some of it said to somebody who has been very vicious to me, Rosie O’Donnell. I said very tough things to her and I think everybody would agree she deserves it and nobody feels sorry for her."

In a Vanity Fair piece about Rosie's brief time on The View, it's clear that this ongoing battle with Trump directly contributed to her exit from the show. Barbara Walters was friends with Trump and repeatedly tried to smooth things over which left Rosie feeling like no one had her back. He continued to slam her in the media and although Walters eventually distanced herself from Trump, the damage was done.

Nowadays, Rosie is the host of the Onward with Rosie O'Donnell podcast which began in March 2023. She has already had an incredible roster of guests that includes Brooke Shields, Jennifer Lewis, and social media influencer Dylan Mulvaney, the trans dancer whose Instagram campaign with Bud Light sparked outrage among conservatives. This is the perfect medium for Rosie who won't have to tiptoe around what she really wants to say.