From Best Guests Ever to Total Silence: What Really Happened Between Howard Stern and Donald Trump

There was a time when Donald Trump was, in Howard’s own words, one of the best guests he ever had on the show. Long before politics entered the picture, Trump was a regular on Stern’s mic — funny, unfiltered, willing to say absolutely anything. It’s some of the most memorable radio in Stern Show history.

So it stung a little differently this week when Trump, speaking to reporters in the Oval Office, claimed he “hasn’t heard the name Howard Stern in a long time” — and suggested Stern’s show only “went down” after he endorsed Hillary Clinton back in 2016. According to Trump, that single decision cost Stern his audience for good.

Here’s the thing: nobody has actually confirmed Stern is leaving SiriusXM. The whole exchange started from an unverified rumor a reporter brought into the room. Stern himself popped up mid-vacation just to reassure fans he’d be back on schedule September 2nd, no drama, no departure announcement.

What makes this sting for longtime fans isn’t the politics — it’s the history. These two weren’t just host and guest. They attended each other’s weddings. They sat courtside together at Knicks games. For years, Trump credited Stern’s show as a place he could really open up. Watching that friendship reduced to a dismissive soundbite feels like watching one more piece of old-school New York media culture quietly fade.

Whatever side of the political aisle you’re on, there’s something undeniably bittersweet about two guys who used to have that much fun together now acting like strangers. Radio built friendships like this one — real, messy, complicated. It’s rare TV or politics leaves room for that kind of nuance anymore.

Fans, be honest: do you remember the old Trump-Stern interviews? Because they don’t make radio like that anymore.