IN THE 90s THEY WEREBEST FRIENDS.IN 2026 TRUMP SAID”I HAVEN’T HEARDTHAT NAME IN YEARS.”
The 30-year relationship between Howard Stern and Donald Trump — told era by era. How the two most recognizable voices in New York went from genuine mutual admiration to one of the most public fallouts in American media history.
There is no relationship in the history of American media quite like the one between Howard Stern and Donald Trump. It lasted three decades, survived multiple divorces (Trump’s), multiple reinventions (Stern’s), and countless public controversies from both sides. It produced some of the most candid moments in the history of celebrity radio. And it ended — publicly, coldly, and completely — in a way that neither man probably would have predicted when they were sharing laughs on the airwaves in the early 1990s.
This is the story of how Howard Stern and Donald Trump went from the two biggest personalities in New York to two men who now pretend they barely know each other. Told era by era. From the beginning.
Through the early and mid-1990s, Donald Trump was a fixture on The Howard Stern Show. He called in regularly, appeared in studio, attended Howard’s birthday parties. The dynamic was genuine — two men who both thrived on attention, both had enormous New York egos, and both found in each other a kind of peer they didn’t often encounter. Howard could match Trump’s bravado. Trump could match Howard’s willingness to say anything.
In 1993, Howard threw himself a birthday party. Trump appeared as a guest and spent an extended time on the phone with Jerry Seinfeld — live on air. They talked about Ivana Trump, Marla Maples, money, fame, relationships. It was pure New York energy: loud, unfiltered, completely entertaining, and utterly unlike anything happening on any other radio show in America.
The friendship was real enough that Howard described Trump as genuinely shocked by the concept of marital fidelity. That level of candor — offhand, unguarded, clearly unrehearsed — was exactly what made these appearances appointment radio. Trump was not performing for Howard’s audience. He was just being himself, with a friend, on a microphone.
The early 2000s saw Trump return to Stern’s show in the context of The Apprentice — his NBC reality show that was pulling 24 million viewers per episode at its peak. These conversations were looser and more self-promotional than the 90s sessions, but they still produced remarkable material. In 2004, Trump and Howard bonded over their shared opposition to the Iraq War and their mutual contempt for George W. Bush — a detail that became historically ironic as the decade unfolded.
They discussed prenuptial agreements, Tom Brady, Mark Cuban, Melania’s career, and Ivanka Trump’s love life. It was, by any measure, still the most unguarded version of Donald Trump available anywhere in American media. Howard’s format did what it always did: made someone feel private when they absolutely were not.
The break point was 2016. Howard endorsed Hillary Clinton for president — publicly, unambiguously, on his show. For Trump, who understood the Stern audience as well as anyone, this was not a neutral act. Stern’s listenership — working-class, mostly male, mostly older, mostly not coastal liberal — was precisely the demographic that Trump was building his political coalition around. Howard had chosen the other side.
“You know when he went down? When he endorsed Hillary Clinton. He lost his audience.” — Donald Trump, Oval Office, 2025
— Trump dismissing Howard when asked about him by a reporter
Howard, for his part, escalated considerably. He said publicly that he “hates” Trump voters. He called them “stupid” on air. He offered to run for president himself, specifically to confront Trump. He became one of the most prominent media voices against the Trump presidency — which meant that the man he had spent a decade trading laughs with had become the thing he was most publicly opposed to.
In 2025, a reporter asked Trump about Howard Stern — specifically about the SiriusXM contract negotiations that had been in the news. Trump’s response was calibrated to land exactly where it did: “Howard Stern — that’s a name I haven’t heard. I used to do his show, we used to have fun. But I haven’t heard that name in a long time.”
From the Oval Office. About a man who still broadcasts to millions of listeners every week. The dismissal was not accidental. Every word of it was chosen. Trump treating Howard Stern like a forgotten footnote — from the most powerful room in America — was the kind of public humiliation that cannot be undone.
As a fan who followed both of them through all of it — the 90s radio gold, The Apprentice era, the political break, the Oval Office dismissal — the honest feeling is complicated. The friendship was real. The radio was genuinely great. And the ending was as ugly as the beginning was fun.
Two New York originals. Both built on saying whatever they wanted. Both discovered, eventually, that saying whatever you want has consequences. Neither one of them would change a word of it. That’s the most Howard and Trump thing about the whole story.
