Howard Stern Revives Old Trump Interviews, Exposing Crude Remarks About Women and Family

NEW YORK — Howard Stern, once a close friend and frequent interviewer of Donald J. Trump, has reignited controversy by resurfacing more than 35 hours of archived radio conversations in which Trump made graphic and objectifying comments about women — including his own daughter Ivanka, his wife Melania, and contestants in beauty pageants he owned.

The revelations, drawn from Stern’s syndicated show between 1993 and 2016, have been compiled and searchable since 2017 on the site Factba.se. They include Trump rating women on a numerical scale, describing Melania as “a great deal” he “got for the right price,” and engaging in extended discussions about Ivanka’s appearance that many listeners found deeply unsettling. In one 2004 exchange, Stern called Ivanka “a piece of ass,” to which Trump responded affirmatively without objection. Stern then asked if Ivanka had breast implants; Trump replied, “No, no, she didn’t. I mean, I would know if she did.”

Trump, who appeared on Stern’s program more than any other major media figure during that period, once described him as one of his “top five guests of all time” for being “wild” and “unfiltered.” Yet the relationship soured after Trump entered politics. Trump now calls Stern “weak” and claims he “dropped him like a dog,” dismissing his former host’s ratings as “very challenged.”

The resurfaced audio has drawn renewed attention amid Trump’s second term, as critics argue it reveals a long-standing pattern of misogyny and objectification. In a 2002 discussion, Trump described Melania’s appearance on a New York billboard as part of “a good deal” he secured. Stern pressed further, asking if she had cellulite; Trump deflected by saying “Melania doesn’t even know what the word cellulite means,” prompting a New York newspaper to publish a story implying she was uninformed.

More disturbing to many are the repeated comments about Ivanka. In 2006, Trump told Stern she was “voluptuous” and “an amazing beauty.” He later repeated in a Rolling Stone interview that if Ivanka were not his daughter, “perhaps I’d be dating her.” Stern also asked about her potential to pose nude for Playboy; Trump said he did not think she would appear inside the magazine but acknowledged she had “a very nice figure.”

As owner of the Miss Universe pageant organization for nearly two decades, Trump admitted to entering dressing rooms where contestants were changing. “I’m inspecting,” he told Stern in 2005. “I want to make sure that everything is good… They’re standing there with no clothes… And you see these incredible-looking women.” He added that he “sort of get[s] away with things like that.”

Stern, who once praised Trump’s candor, now uses the same recordings to criticize him. In recent interviews promoting his book, Stern has called Trump “demented” and suggested he would benefit from psychotherapy, citing what he sees as severe narcissism and a lack of empathy. The former shock jock has expressed regret over giving Trump such an unfiltered platform, noting that the interviews now serve as permanent evidence of attitudes many find disqualifying for a president.

Trump has not directly addressed the specific recordings in recent days but has continued to attack Stern personally, calling him “weak” and claiming their falling-out stemmed from declining ratings. The White House did not respond to requests for comment.

The audio archive has taken on new relevance as Trump faces ongoing scrutiny over his past behavior toward women. Legal experts note that while the remarks are not criminal, they reinforce long-standing allegations of misogyny that have shadowed his public life. For Stern, the revival of these clips represents both a personal reckoning and a journalistic one: the same openness that once made Trump a “great guest” now stands as a damning record.

As the 2026 midterms approach, the resurfaced interviews have fueled Democratic messaging that Trump’s character remains unchanged. Whether they shift voter sentiment remains unclear, but they have once again placed private conversations at the center of public debate — this time, with the full weight of hindsight.