It is weird to think about now, but for about two decades, Howard Stern and Donald Trump were basically two peas in a pod. If you tuned into 102.7 WXRK in New York during the late 90s, there was a high chance you’d hear a gravelly voice calling in to dish on Miss Universe ratings or the "voluptuous" nature of his own daughter.
That voice belonged to Trump. He wasn't the 45th and 47th President back then. He was just "The Donald," a Manhattan real estate mogul who treated the Howard Stern show like his personal living room. They were buddies. They were icons of a specific brand of New York machismo that defined the pre-social media era.
But then, politics happened.
The Howard Stern Donald Trump Dynamic: A Match Made in Tabloid Heaven
Back in the day, Howard Stern was the only place where Donald Trump could be truly "unfiltered"—which is saying something for a guy who has built a career on having no filter. Between 1993 and 2015, Trump appeared on the show roughly 50 times. That is an insane amount of airtime for a billionaire.
Why did he do it? Honestly, it was a symbiotic relationship. Howard got the biggest name in New York real estate to say things that would make a sailor blush, and Trump got to reach millions of "regular guys" who viewed his lifestyle as the ultimate American dream.
They talked about everything. And I mean everything. They discussed whether it was okay to date a woman over 35 (Trump’s famous "check-out time" comment), the physical attributes of various supermodels, and even Trump’s germophobia. Howard would poke and prod, and Trump, ever the entertainer, would lean into the "locker room talk" with zero hesitation.
The Famous—and Infamous—Interviews
One of the most bizarre moments happened in 1999. Trump actually put his then-girlfriend, Melania Knauss, on the phone with Howard while she was in bed. It was uncomfortable, voyeuristic, and exactly the kind of thing that made Stern the "King of All Media."
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Then there were the comments about Ivanka. In 2004, Stern called Ivanka a "piece of a**," and Trump didn't push back. Instead, he agreed, noting she had been "voluptuous" her whole life. These weren't "gotcha" moments at the time. They were two guys being crude for an audience that ate it up.
But these tapes didn't stay in the archives. When the 2016 election rolled around, the Howard Stern Donald Trump archives became a gold mine for political opposition.
Why Howard Stern Refused to "Betray" Trump in 2016
When the Access Hollywood "grab 'em by the pussy" tape leaked, the world turned its eyes toward Howard Stern. Surely, people thought, Howard has hundreds of hours of even worse stuff. The pressure on Stern to release the full, unedited archives was immense.
He wouldn't do it.
Howard actually took a surprisingly principled stand. He argued that Trump came on his show to be an entertainer. He felt that playing those tapes to "f**k someone over" would be a betrayal of the guest-host relationship. Howard said:
"I fully knew what I was doing when I interviewed Trump. I knew I had a guy who loved to talk about sex... These are avenues I went down because I knew it would entertain the audience."
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Even though Stern was a vocal supporter of Hillary Clinton, he didn't want to use his platform as a political weapon. That’s a nuance that a lot of people miss. He hated Trump’s politics, but he respected the "code" of the radio studio.
The 2024 Context: From Friends to Bitter Rivals
Fast forward to the present. The friendship is dead. Buried. Done.
If you listen to Stern now, he sounds like a completely different person than the guy from 1995. Howard went through years of psychotherapy and "evolved." He’s now a self-described "woke" liberal who broadcasts from his basement in the Hamptons. Trump, meanwhile, stayed exactly the same—or perhaps became a more intense version of his 90s persona.
The "Mental Health" Theory
Howard has a specific theory about why Trump ran for president in the first place. He’s said on air multiple times that he thinks Trump never actually wanted to win. He believes Trump ran as a publicity stunt to get a better contract for The Apprentice and was "pissed" when he actually won.
According to Stern, the presidency was the worst thing that could have happened to Trump’s mental health. Why? Because Trump desperately wants to be loved by the "elites"—the Hollywood stars and the New York Times editors who now despise him. By becoming the leader of the MAGA movement, he essentially exiled himself from the social circles he spent forty years trying to conquer.
The Evolution of the Howard Stern Donald Trump Relationship
To understand how we got here, you have to look at the timeline. It wasn't one single fight. It was a slow-motion car crash.
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- The 90s Era: Pure bromance. Trump is a regular caller. Howard attends Trump's wedding to Melania in 2005.
- The Apprentice Era: Howard helps promote the show. Trump is the ultimate success story.
- The 2016 Pivot: Trump asks Howard to speak for him at the Republican National Convention. Howard says no. The distance begins.
- The Presidency: Howard starts criticizing Trump’s policies and his handle on the COVID-19 pandemic.
- The Current State: Trump calls Howard a "broken-down shock jock." Howard says he’s "proud" to be woke and thinks Trump is a threat to democracy.
It’s a classic New York story of two guys who grew up, but in completely opposite directions.
What People Get Wrong
Most people think Stern "turned" on Trump because of politics. That’s only half the story. The truth is that Stern changed his entire personality. He stopped being the guy who threw baloney at strippers and started being the guy who interviews Oprah about her childhood trauma.
Trump didn't change; Howard did. And for a guy like Trump, who prizes loyalty above all else, Howard’s evolution felt like the ultimate betrayal.
The Impact on Media Today
The Howard Stern Donald Trump saga is actually a blueprint for how modern media works. It shows the power of "alternative" media. Long before Joe Biden was going on SmartLess or Trump was doing a three-hour marathon with Joe Rogan, Trump was using Stern to bypass the traditional gatekeepers.
He knew that the "Stern Show" audience was his base. He was "podcasting" before podcasts existed.
Actionable Insights: How to Navigate the Archives
If you're looking to dive deeper into this history, here is how to find the real story without the political spin:
- Listen to the 2004-2006 Interviews: This is the "peak" of their interaction. You can find many of these on YouTube or archived fan sites. It provides the best context for their original dynamic.
- Check the Transcripts: If you don't want to listen to hours of audio, search for the "CNN KFile" reports from 2016. They did the heavy lifting of transcribing the most controversial segments.
- Observe the "New" Howard: Listen to a recent Stern interview (like his 2024 sit-down with Joe Biden) and compare it to a 1990s Trump interview. The contrast in tone, empathy, and vocabulary is a masterclass in personal rebranding.
- Look for the "Miss Universe" Tapes: These are where Trump is most candid about his business dealings and his "inspection" of the contestants. It explains a lot about his worldview regarding power and access.
Understanding the Howard Stern Donald Trump relationship isn't just about celebrity gossip. It’s about understanding how the lines between entertainment, fame, and political power became permanently blurred in America. You can't have the Trump presidency without the Howard Stern years that paved the way.