The Trump Files: Donald’s Most Ridiculous Appearance on Howard Stern’s Show

Ivylise Simones

For indispensable reporting on the coronavirus crisis, the election, and more, subscribe to the Mother Jones Daily newsletter.


Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of presumptive GOP nominee Donald Trump.

Donald Trump has had plenty of unsavory moments as a guest on Howard Stern’s various shows—where he has often joined the host in making boorish and misogynistic comments—but a 2001 appearance on Stern’s radio show was particularly ugly, when Trump engaged in an on-air showdown with gossip columnist AJ Benza.

Things started out calmly enough when Trump called into the show, which featured Benza as a studio guest. “AJ’s a nice guy,” Trump told Stern. “I like him, even though I hear he said negative things about me in his book.” That book, Fame: Ain’t It a Bitch, accused Trump of stealing Benza’s ex-girlfriend, model Kara Young. Trump pleaded innocence: “Hey, AJ, nobody told me I was stealing your girlfriend.”

The détente didn’t last long. Within minutes, Trump was bragging about having slept with Young, Benza was making creepy threats to bed Trump’s daughter Ivanka, and both men were questioning each other’s hair.

“While you were getting onto the plane to go to California thinking that she was your girlfriend, okay, she was some place that you wouldn’t have been very happy with,” Trump told Benza.

“I can’t wait till your little daughter gets a little older for me,” Benza said.

“[Young] told me you were losing your hair, AJ, and you’re going for transplants,” Trump said.

“Oh, shut up, you got plugs,” Benza fired back. “Does the world know that?”

The fight went on for half an hour. Stern got Young herself on the phone, and she said what many listeners were probably thinking: “I think it’s sad that two grown men are doing this.”

DEMOCRACY DOES NOT EXIST...

without free and fair elections, a vigorous free press, and engaged citizens to reclaim power from those who abuse it.

In this election year unlike any other—against a backdrop of a pandemic, an economic crisis, racial reckoning, and so much daily crazy—Mother Jones' journalism is driven by one simple question: Will America will move closer to, or further from, justice and equity in the years to come?

If you're able to, please join us in this mission with a donation today. Our reporting right now is focused on voting rights and election security, corruption, disinformation, racial and gender equity, and the climate crisis. We can’t do it without the support of readers like you, and we need to give it everything we've got between now and November. Thank you.

DEMOCRACY DOES NOT EXIST...

without free and fair elections, a vigorous free press, and engaged citizens to reclaim power from those who abuse it.

In this election year unlike any other—against a backdrop of a pandemic, an economic crisis, racial reckoning, and so much daily crazy—Mother Jones' journalism is driven by one simple question: Will America will move closer to, or further from, justice and equity in the years to come?

If you're able to, please join us in this mission with a donation today. Our reporting right now is focused on voting rights and election security, corruption, disinformation, racial and gender equity, and the climate crisis. We can’t do it without the support of readers like you, and we need to give it everything we've got between now and November. Thank you.

We Recommend

Latest

Sign up for our newsletters

Subscribe and we'll send Mother Jones straight to your inbox.

Get our award-winning magazine

Save big on a full year of investigations, ideas, and insights.

Subscribe

Support our journalism

Help Mother Jones' reporters dig deep with a tax-deductible donation.

Donate