Virginia Heffernan is author of Magic and Loss: The Internet as Art.

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.

Time for a victory lap, Stern-style. “Can I feel your ass, Donald? Can I feel your ass?” Stern says, to howls from his studio sidekicks. “Check you for your wallet.” Trump had indeed been pickpocketed of his dignity.

The dignity theft, complete with Stern’s whoops of alpha dog dominance, would have delighted Stern’s regular listeners. After all, his mandate was, hour after hour, to induct new members into his notorious Wack Pack, the rotating parade of some 70 oddballs who regularly appeared on the show to be bullied by Stern, who gave them names like “Wendy the Retard,” “Crackhead Bob” and “Joe Cancer.” Here, Stern seems to have snagged another one, if only implicitly. Call him “Donald the Douchebag.”

The Wack Pack was a big deal in New York two decades ago, a part of the pushback against the sanitization of Times Square. Freak shows, neo-burlesque and clown schools were staging a comeback. The Wack Pack, then, was a repertory company of regular guests whom Stern caricatured for their deformities, personality disorders, speech impediments—a group so vulnerable and fame-hungry that they consented to be framed publicly as freaks. (In this way, they prefigured unpaid performers on shows like The Bachelor, The Real Housewives and cable news.)

The members of the Wack Pack, however, were at least groomed to believe they were in on Stern’s joke. The shrewder among them (“Hank the Angry Drunken Dwarf,” say) even were in on the joke, and managed to parlay Stern’s brutal hazing into some legit show biz moments.

Trump, however, was not in on the joke.

Listening now to the old Stern-Trump scenes, Trump clearly has none of Hank the Angry Drunken Dwarf’s integrity. At one point in 1997, Trump was asked about a list he had made of 10 women he considered the world’s most beautiful. It seems the list was almost entirely opportunistic, though—a way for Trump to curry favor with women who might help him rehabilitate his career (Diane Sawyer, for example). But Stern didn’t let the list gain for Trump a micron of respectability. Instead, he treated it as a lecherous artifact and made Trump squirm as he tried neither to disavow the women nor to join Stern in raunchy fantasies about them.

Trump couldn’t figure a way out of this monkey trap, as when Stern asked him about Cindy Crawford. “Her husband is a tenant. He’s a great guy,” Trump said, weakly. “Her husband is doing beautifully at his restaurant.” So, Stern persisted, determined to return Trump to the sexism that sells: Did he want to bang this guy’s wife or not? There was nothing left for Trump to do but chumpishly laugh along. After an appearance like this one, the audience is left with the impression that Trump is more outside the realm of polite society than ever, spending his workday pruriently ogling successful married women he doesn’t stand a chance with.

At last, Trump emerges in the Stern tapes as a kind of humorless George Hamilton figure—a lecherous has-been measuring his march to the grave in New York Post mentions. (Trump on the Stern show is, in fact, a big defender of the punchliner Hamilton, his tan-twin on the C-list.) To keep Douchebag Donald in character, Stern blows no end of noxious smoke, pushing Trump to preen pathetically and act the baller. But Trump never tells him off. Instead, he seems cravenly eager to please Stern, self-styled King of all Media, whose unlikely charisma—unceasingly onanistic and anhedonic, using others only to spark his disgust or his libido—seemed infinitely bankable at the time.

But maybe a Wack Pack wannabe shouldn’t have commented on geopolitics. In 2002, calling in to Stern’s show on the first anniversary of the 9/11 attacks, Trump, who by then had published The Art of the Comeback but was still two years away from The Apprentice, initially sounded self-assured. He started off plumping for—what else—the housing market as a sure thing, an antidote to “the Enrons, the Global Crossings, that garbage.”

Bored, Stern smartly steered Trump back into douchebag mode, with a nice assist from his deceptively gentle co-host Robin Quivers, a nurse and onetime second lieutenant in the Air Force who also works with the United Nations to help exploited girls around the globe. As Quivers oohed and ahhed cartoonishly at Trump’s BMOC routine, like a sweetheart with the Fonz, she got him to reflect nauseatingly on how on 9/11 compromised the view from his penthouse apartment: “I have two windows that are focused on the building. … You can’t believe that, after looking for 20 years at the World Trade Center, you can’t believe they’re not there.”

But Stern and Quivers in that interview were only softening Trump up for the rope-a-dope moment that has been so consequential in the 2016 election. Probing Trump’s thoughts on 9/11, they got him to complain that “we really don’t know the enemy.” Fair point, but it was the days of drumbeats: The hawks were gunning for war in Iraq. Confused about that enemy, Trump suddenly seemed perilously close to teeing up an emasculated antiwar position. Stern saw an angle. “Are you for invading Iraq?” Stern asked. “Yeah … I guess so,” Trump said. Without assenting, he would have been stuck making the case for diplomacy or police action—something consistent with an inchoate enemy—which is discourse way too subtle to interest Stern or, as the world now knows, Trump.

Can I feel your ass, Donald?

There was another time that Trump submitted even more fully to Stern—tapping out, as they say in Ultimate Fighting. Back in the discussion of Trump’s list of beautiful women, Quivers seemed to lose patience when lecherous talk of Trump’s daughter Ivanka, who was then 19, started.

“I was surprised she wasn’t on the list!” Quivers said, suddenly, of Ivanka. (In 1995, Quivers published a memoir, Quivers: A Life, in which she recounted having been a victim of sexual abuse by her father.) Hoots at Quivers’ audacity followed from the peanut gallery.

“That would be a front-page story,” Trump said.

“Would you like me to put her on my list?” Stern said, incredulous. “Maybe I’ll date your daughter.”

Astonishingly, Trump warmed to the idea. “She has very good taste,” Trump said. “She’d probably find you very attractive.”

The daughter-pimping moment met with audible shock, even on the original shock-jock set.

Quivers knew she had to keep Donald coming back, but you can hear the contrivance in her sign-off to him: “Donald, I love you, you know that.”

Trump’s run on “The Howard Stern Show” came to a close right around 2004, when he met his next Svengali: Mark Burnett, the creator of The Apprentice. Trump was slated to play a powerful kingmaker by then, and to dramatize both his setbacks and his ingenuity. Donald the Douchebag didn’t work in that context, so Burnett and Trump dreamed up what you might call the Brutal Tyrant, which worked so well that Trump took it to the political stage.

Stern, for his part, has said he’s supporting Clinton in the presidential election. “I don’t dislike Trump as a candidate,” he told the Washington Post, “but I am absolutely enamored by Hillary. And I’ve told Donald that.” But Wendy the Retard (a seemingly bright, if exceedingly accommodating woman, who uses this moniker herself) spoke recently on the SiriusXM show about politics. Wendy is voting for Trump. Stern is ever the ringmaster, but his Wack Pack sticks together. Trump, however, still isn’t in on the joke.

Correction: An earlier version of this article said Howard Stern had not said for whom he will vote for president; he has said he’s supporting Hillary Clinton.