Inside Penn Jillette's Past Drama With Donald Trump

Donald Trump has put many people on blast via his now-defunct Twitter over the years. Penn Jillette, best known as one-half of the magic-comedy act Penn and Teller, targeted by inflammatory Trump tweets in 2015. "I hear @PennJillette show on Broadway is terrible," Trump tweeted at the time while adding that Jillette's appearances on "Celebrity Apprentice" in 2012 and 2013 were the only reason the comedian was still relevant, via the Las Vegas Sun. "I loved firing goofball atheist Penn @PennJillette on The Apprentice," the former reality show host added. Friction rose between the two after Jillette took shots at the reality show in his book "Every Day Is An Atheist's Holiday" between appearances on the series. "The secret truth of 'Celebrity Apprentice' is that it isn't very hard. ... [It] is easy like junior high is easy," Jillette wrote.

When Trump was running for president in 2016, Jillette said his time on the NBC reality show made him especially nervous. "The problem is, I know Trump, so my optimism has been squashed like a baby bird," the comedian told Newsweek at the time. While Trump was in the oval office, Jillette spoke about how unhinged the then-president could be. "He's crazy and he's venal. He's empty. He's obsessed with what anybody says about him at any time," Jillette said while appearing on "The Joe Rogan Experience" in 2019, via Los Angeles Magazine. Later, Jillette clarified why Trump took particular exception with the former "Celebrity Apprentice" contestant. 

How Penn Jillette's relationship with Donald Trump changed

The relationship between Penn Jillette and Donald Trump dated back to before the real estate tycoon had a real shot at becoming president. "I knew him back when he was destroying Atlantic City. I knew him when he was just a joke," the Penn and Teller performer said on Anna Faris' "Unqualified" podcast on November 16. Jillette claimed that Donald Trump Jr. used to mention how much his father liked the comedian. 

That dynamic changed after Jillette's appearances on "Celebrity Apprentice." The magician was named as Trump's seventh most-hated person, in an article by The New York Times. According to the "Random" author, Trump was enraged by comments Jillette made during his presidential campaign. "Because I was the first person that he knew personally, who said publicly I would not support him for president," Jillette said. During his interview on the "Unqualified" podcast, Jillette discussed how he initially got along with the former president. "I mean, I've been friends and worked with people who are very eccentric and I do very well," he told Faris. Jillette was quick to add that his opinion about Trump changed once the presidency became a possibility.

In 2019, Jillette claimed he was open to changing his mind about Trump if he would have ended the country's military occupation in Afghanistan. "But if he stops killing people, that's more important to me I suppose than one's choice of words on Twitter," Jillette told the Orlando Sentinel.