How Rosie O’Donnell’s brutal takedown of Donald Trump led to a vicious 20-year feud

Rosie O’Donnell and Donald Trump have been publicly feuding for years (Pictures: Getty)

Rosie O’Donnell has made headlines following her recent comments on her ongoing battle with Donald Trump, sparking questions over how their long-running feud began.

Earlier this month, the comedian, 62, confirmed that she had started a new life in Ireland, joining a string of famous faces who had left the US following the controversial politician’s second Presidency.

Touching on her decision to flee, she declared that the 78-year-old ‘has had it out for her’ for years – stemming from remarks she made on the View nearly two decades ago.

Since that fateful episode aired, they have continued to trade barbs on social media, with the US leader deeming her ‘a real loser’ and ‘obnoxious’.

Here is a rundown of where their drama started, and what led to the TV favorite leaving America.

How Rosie O’Donnell’s feud with Donald Trump began

O’Donnell made her feelings about Trump very clear during a discussion about a controversial Miss USA winner on the View in 2006, and didn’t hold back about the then-TV star, who owned the pageant at the time.

After winner Tara Conner was accused of doing drugs and drinking underage, he held a press conference to insist that she should be ‘given a second chance’, a stance that the host found ‘annoying’.

‘He annoys me on a multitude of levels,’ she fumed to her fellow panelist. ‘He’s the moral authority – 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.

‘Donald, sit and spin, my friend. I don’t enjoy him.’

O’Donnell then called out his reputation as a self-made man’ and the financial help he allegedly received from his father.

Rosie called out Trump on the View (Picture: Shutterstock)

‘He’s going to sue me but he’ll be bankrupt by that time, so I won’t have to worry,’ she said to gasps from her colleagues.

‘I think this man is like one of those snake-oil salesmen on Little House On The Prairie…

‘That’s my opinion, I don’t enjoy him.’

What has Donald Trump said about Rosie O’Donnell?

According to People Magazine, Trump slammed her words and claimed that his dad ‘never gave [him] tons of money’, branding her ‘terrible’, insisting her statements were ‘false’.

Threatening legal action, he added: ‘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.’

The New York Times reports that he later called her ‘disgusting’ and ‘a slob’ with ‘a fat, ugly face’ on Entertainment Tonight, describing her as a ‘very unattractive person, both inside and out’.

The politician hit back in the press (Picture: AFP)

Their battle has raged on over the years, leading to Trump responding to O’Donnell’s 2011 engagement news with a less-than-congratulatory message on Twitter.

‘I feel sorry for Rosie ‘s new partner in love whose parents are devastated at the thought of their daughter being with @Rosie –a true loser,’ he posted.

Two years later, he replied to a Twitter user, insisting that their spat ‘will never end’.

In 2014, he took aim at her once again, tweeting: ‘Rosie is crude, rude, obnoxious and dumb – other than that I like her very much!’

He has made his thoughts known on social media (Picture: Getty)

That same year, the SMILF actress said that their public sparring had led to the ‘most bullying’ that she had experienced in her life.

Unpacking their fraught history in a chat with People Magazine, she remarked: ‘Probably the Trump stuff was the most bullying I ever experienced in my life, including as a child.

‘It was national, and it was sanctioned societally. Whether I deserved it is up to your own interpretation.’

This did little to stop Trump, as he continued to bash O’Donnell publicly during his first Presidential campaign.

Rosie revealed she had experienced huge ‘bullying’ (Picture: Getty)

‘Somebody who has been very vicious to me, Rosie O’Donnell,’ he announced during a debate with Hillary Clinton in 2016, via the New York Times.

‘I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her.’

Hitting back in a now-deleted Twitter post, O’Donnell branded him an ‘orange anus’.

Following his first election, she spoke candidly to W Magazine about their tumultuous history, and questioned whether she could ‘live through’ his reign.

Trump continued to call Rosie out on Twitter (Picture: Getty)

‘Unbeknownst to me, for reasons I can’t really still figure out, he was allowed with impunity to brutally assault me and my character for a decade,’ she said in 2017.

‘No one – not the National Organization For Women, not Gloria Steinem, no one – stood up and said, “What the hell are you doing?” It was laughed about.

‘When it was only me in that arena, it was a very lonely, isolated and depressing place to be. Even though [people say], “Oh you started it,” well I actually told the truth about him on a show where my job was to talk about pop culture.

‘I seriously worry whether I personally will be able to live through [his presidency] and whether the nation will be able to live through it and survive. It’s a terrifying concept, on the brink of nuclear war with a madman in charge.’

Why did Rosie O’Donnell leave America?