Barbara Walters biggest interviews: Legend interviewed everyone from Monica Lewinsky to Donald Trump

Barbara Walters‘ legendary status in the world of American broadcast journalism was long established before her death on December 30 at the age of 93. 

Walters once said in a 2014 speech at Harvard University that a journalist’s most important quality was curiosity. 

That quality was displayed throughout her career, especially when she interviewed the most famous news makers of the day. 

Her interview with Monica Lewinsky in 1999 smashed TV ratings records for a news special as she got Bill Clinton‘s brief paramour to apologize to Hillary. Years earlier, she was one of the first journalists to take Donald Trump to task over his false claims of brilliance in real estate. 

Walters’ interviews were not all conducted from the safety of air-conditioned studios, in 1977 she spent 10 days in the mountains of Cuba interviewing Fidel Castro, gaining his trust to the extent that many thought they were having an affair – they weren’t.  

Walters’ interview with Monica Lewinsky in 1999 was one of the highest rated shows in American history, garnering nearly 80 million viewers for ABC’s 20/20

In the interview, Lewinsky apologized to Hillary and Chelsea Clinton and spoke about her regrets at ever getting involved with the then-president

In 1999, Walters interviewed the then-most talked about woman in the world, Monica Lewinsky, just a year after the former White House intern’s brief affair with Bill Clinton broke. 

The interview was one of the highest rated shows in American history, garnering nearly 80 million viewers for ABC’s 20/20. Walters once said that executives at the network told her that nobody would watch the proposed two hour special. 

In the interview, Lewinsky apologized to Hillary and Chelsea Clinton and spoke about her regrets at ever getting involved with the then-president. Later, in 2018, Lewinsky said that she was still waiting on an apology from the former governor of Arkansas. 

While in an infamous moment, the pair discussed Lewinsky showing her thong to Clinton, Walters appeared to chastise the former intern saying, ‘Where did you get the nerve? I mean, who does that?’ 

Lewinsky shot back, ‘If you take my word for it, it was a small, subtle, flirtatious gesture. And that’s me.’ 

Arguably the most famous moment of the interview came when Walters asked Lewinsky if she was still in love with Clinton. 

Lewinsky replied, ‘No. Sometimes I have warm feelings, sometimes I’m proud of him still, and sometimes I hate his guts. And, um, he makes me sick.’

Arguably the most famous moment of the interview came when Walters asked Lewinsky if she was still in love with Clinton

Walters followed that up with, ‘What will you tell your children, when you have them?’ She replied, ‘Mommy made a big mistake.’

Lewinsky is known to keep her private life very private but she is not believed to be married. In 2015, she joked to People Magazine in an interview, ‘I’ve promised Barbara Walters a dance at my wedding, so I hope to make good on that promise some day!’ 

When Walters left The View that year, Lewinsky was rumored to take a possible role on the show. 

Walters first encountered Donald Trump in an August 1990 interview when the 45th president was still just a New York real estate magnate

Walters took him to task over his claims that his deal to buy the Plaza Hotel for $407.5 million in 1988 was a ‘great deal’

Walters was proved to be right when five years after the interview aired, Trump sold the hotel at a loss of nearly $80 million

Walters first encountered Donald Trump in an August 1990 interview when the 45th president was still just a New York real estate magnate. 

Unlike many in the media who enjoyed Trump’s bombastic personality, Walters took him to task over his claims that his deal to buy the Plaza Hotel for $407.5 million in 1988 was a ‘great deal.’

Trump said, ‘Well, I don’t know what the bankers have said. The Plaza is a very valuable property. Everybody told me “You paid too much, you paid too much.” Now, they’re all saying “What a great deal he made.”‘ Walters replied, ‘No, they’re not.’

She was proved to be right when five years after the interview aired, Trump sold the hotel at a loss of nearly $80 million. 

Walters chastised Trump at one point saying: ‘Being on the verge of bankruptcy? Being bailed out by the banks? Skating on thin ice and almost drowning? That’s a businessman to be admired?’

The same year, the New York Times reported that banks were threatening to foreclose on loans to Trump because of his many failed business ventures. 

In 2015, Walters asked Trump what he would like his political legacy to be, he replied, ‘Victory’

Walters met up with Trump again in 2015 when she interviewed him around the time he began his first presidential campaign. 

Following Trump’s statements at the time, Walters asked him out right, ‘Are you a bigot?’

He responded, ‘Not at all. Probably the least of anybody you’ve ever met.’

When Walters asked him to clarify his answer, he went on, ‘Because I’m not. I’m a person that has common sense. I’m a smart person. I know how to run things. I know how to make America great again. This is about making America great again.’

Towards the end of the interview, Walters asked Trump, ‘Let’s say you win the presidency. When you leave office — in one word — what would you like your legacy to be?’ He answered, ‘Victory.’

One of Walters’ first groundbreaking interviews was with Cuban leader Fidel Castro in 1977

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The apparent closeness that Walters was able to display towards Castro led to rumors that the pair had a romantic relationship

One of Walters’ first groundbreaking interviews was with Cuban leader Fidel Castro in 1977, less than 20 years after the communist had seized control of the Caribbean nation.  

The apparent closeness that Walters was able to display towards Castro led to rumors that the pair had a romantic relationship. She said those rumors were false in an interview with People Magazine. 

In the same interview, Walters said that she traveled with Castro through the mountains of Cuba for 10 days, at times holding his gun for him. She told People, ‘Though he could be charming, he was also a dictator. People thought we had a romance, but we never did.’

During their time together, Castro made Walters a grilled cheese sandwich and told her that he would shave off his famed beard if the US government lifted the trade embargo. 

Another famous statement in the interview saw Castro declare that he did not believe in American-style democracy, despite promising free elections in Cuba within a year of seizing power. 

During the interview, Castro said that he would shave off his famed beard if the US government lifted the trade embargo

Later, Walters became the first American in 20 years to cross the Bay of Pigs.

The dictator also told Walters that he thought the US and Cuba would formalize their relationship again during President Jimmy Carter’s second term in office. Carter never got a second term and was defeated by Ronald Reagan in one of the biggest electoral landslides in American history. 

The two did another interview in 2002, Walters said that the interview was not as memorable because more was generally known about Castro and it was not as big of a bombshell.