How Howard Stern Owned Donald Trump Fourth Estate The Donald fancied himself a player in the ’90s, but the shock jock knew just how to play him. Now that’s back to haunt the candidate. To anyone who’s listened to “The Howard Stern Show” since it hit the national airwaves in 1986, Stern’s name still conjures the snicker of adolescent dirty talk, and the occasional sicko comment about Columbine or the developmentally disabled. But now, to the “WTF” of his own audience, Stern has emerged at the center of the national political conversation, a ghost in the machine of the 2016 presidential campaign. It was on Stern’s show, after all, that Donald Trump, then a playboy real estate mogul, called former Miss Universe turned Hillary Clinton supporter Alicia Machado an “eating machine.” It was on Stern’s show that Trump now infamously said he supported the Iraq War (“I guess so”)—a recording that flatly disproves his countless claims he was against it. On Stern’s show, Trump also said it’s “hard to be a 10” if a woman is flat-chested and called the challenge of avoiding STDs his “personal Vietnam.” If the political class is appalled by the notion that anything from the morass of ’90s shock-jock radio could become part of a presidential race, it may be just as surprising to Stern’s fans, who proudly embraced the outsider-ness of a guy who couldn’t seem further from inside-the-Beltway political chatter. But surprising as Stern’s sudden arrival at the center of American politics is, the Stern-Trump encounters are also strikingly revealing—showcasing a strange, mutually manipulative relationship that tells us a lot about both men. Age has chastened Stern, who’s now a more searching interviewer on SiriusXM, as the New York Times recently noted, but he was ascendant at the time, still playing the famous, if haggard, firebrand surrounded in-studio by his team of carnies. Trump, meanwhile, was in personal and professional trouble, fishing for any publicity he could get, and in Stern, he found someone who was willing to put him on national radio, over and over—some two dozen times in the ’90s and the aughts, according to counts by BuzzFeed and the Huffington Post. This much-craved publicity, of course, came at price: Stern has long had a devilish talent for lulling guests into a false sense of security—and then luring them into rhetorical traps. He casts his guests in a burlesque he scripts for them, and cattle-prods them into playing their parts, first fawning over them until they feel like celebrities, then bringing down the hammer of humiliation. He’s a diabolically domineering scene partner. No interviewer has ever been as adroit with treacherous leading questions in the vein of “When did you stop beating your wife?” Stern, in other words, gets people to publicly embrace their worst selves—and say things they live to regret. That’s exactly what happened with Trump. Today, as the Republican nominee, he may fashion himself as a boss and a master of the universe. But what comes across in old tapes of the show, resurfaced recently by BuzzFeed and other outlets, is that Trump, like many of Stern’s guests, was often the one being played. By nailing him as a buffoon and then—unkindest cut—forcing him to kiss the Howard Stern ring, Stern and his co-anchor, Robin Quivers, created a series of broadcasts that today showcase not just Trump’s misogyny but his ready submission to sharper minds. Why would people subject themselves to Stern’s hazing? Generally, his guests in those days—if not strippers and professional opera buffa types—had to have been brought pretty low, so that a combination of psychological fragility and hunger for celebrity made them vulnerable to his mock camaraderie. That’s why it’s important to remember that Trump in the period of his appearances on the show was deeply in the red. By the time he was a regular, he had blown it all in Atlantic City, run out on his vendors, left his imperious first wife, Ivana, for the commoner Marla Maples, earned the yearlong silent treatment of his namesake son and reported a loss of nearly a billion dollars. (Even a businessman of cognitive impairment would have to sweat that one.) His 1987 business advice memoir, The Art of the Deal, which briefly conferred valor on Trump’s scattershot career, was now a distant memory. Trump’s gilded glory belonged to the suddenly despised ’80s. But Stern took Trump’s calls, and even had him into the studio. He gave Trump free airtime, as would cable news much later. And so Trump became dependent on the shock jock. He even admitted at times to being addicted to Stern’s show, telling Stern during one episode that he was late to at least one “really important” meeting, because he couldn’t tear himself away from the broadcast. Trump’s attention was evidently sliding off the dreary business of becoming solvent again. He was finding his calling as a carny. Stern, of course, welcomed Trump to the show, like Willy Wonka with Augustus Gloop.But then he began the rapid-fire questions, shot with plenty of torque, so as to elicit unwholesome revelations. Take, for example, the Stern question that led to Trump’s assertion in 1997 that he could have “gotten” Princess Diana. No other cross-examiner could get away with this. Stern, out of nowhere, with zero reference: “Why do people think it’s egotistical of you to say you could’ve gotten with Lady Di? You could’ve gotten her, right? You could’ve nailed her.” “I think I could have,” Trump responds, uncertainly. But, with Stern’s nudging, he goes on to appraise the appearance of Diana—skin, height, etc., as if she were a horse—using the tone of sadistic connoisseurship he also used when talking about Machado. With this, Stern knows he’s got his checkmate. A fool’s mate, actually. Radio gold. Only a few sentences from Stern, and Trump has stooped to the show’s level of discussing every woman—and a princess, no less, who had recently died tragically—as though she were a stripper.