There’s Wisconsin and there’s “The Howard Stern Show.” Add the legendary shock jock’s platform to the list of places Hillary Clinton should have campaigned in 2016. Stern makes that case persuasively in his latest book, which offers some unlikely insight into how Donald Trump managed to beat the former secretary of state, smack in the middle of wild interviews with Courtney Love, Michael J. Fox, and the Kardashians.
Clinton clearly wanted nothing to do with Stern, so he stuffed her into the book anyway. “Howard Stern Comes Again” is a mix of celebrity interview transcripts organized into subsections including “Drugs & Sobriety,” “Money & Fame,” and “Sex & Relationships.” Stern included 11 Trump interviews, spacing them out chronologically from 1995 to 2015. “Hillary Clinton: The Interview That Never Happened” falls under “Religion & Spirituality,” bookended by interviews with Amy Poehler and Trump himself.
It tells the tale of Stern’s desperate quest to get an interview with Clinton, whose campaign he passionately supported. “I don’t think I’ve ever tried harder to get a guest than I did with Hillary Clinton in the run-up to the 2016 election,” he writes.
Stern tried everything. He greenlit two previously declined profile attempts, one in The New York Times and one in The Washington Post, with the intent of assuring Clinton “she’d be in good hands.” He had an unnamed “network honcho” who happened to be “a huge financial backer of Hillary” offer her a television special with Stern (Trump would be given one as well). Nothing worked.
“I’m telling you, I was obsessed with this. I was Captain Ahab. I wanted it more than anything,” says Stern. Alas, Clinton could not be convinced.
It’s a mistake that may have proven fatal, according to Stern, who said he sensed Clinton’s troubles earlier than others thanks to his listenership in swing states. “I know these people,” Stern writes. “They’ve been listening to me my entire career. I could tell that they were just not feeling Hillary and that they were really embracing Donald.”
That contrast persisted. “Then I saw her in the debates,” Stern remembers. “Donald was shredding her. He knew how to do this. He was talking like a dude. He was saying things in a clear and definite way. People were digging it.”
Stern laments Clinton’s missed opportunity, at first stopping short of saying an interview with him would have “tipped the election,” but ultimately concluding it “might’ve.” He thinks of a hypothetical truck driver or contractor or store owner who may have heard Clinton on the show, “talking about her passion for people,” and been “d-mn impressed.”
It’s perfectly plausible. Stern’s talent these days is coaxing celebrities into candor. In the Clinton chapter he points to all the times people have told him they changed their minds about a particular guest after hearing them on his show. Stern assumes Clinton never took him up on the offer because she saw it as a “gamble,” and thought the election was “in the bag.” That, of course, would never stop Trump. This isn’t to say Americans need their presidents to be Stern guests, just that his failed bid to secure an interview with Clinton emphasizes the contrast that killed her electoral hopes.
Trump has instincts for connecting with the middle of the country that years of consultant-driven campaigning can’t teach. In the heat of presidential election, with polling skewing clearly in her favor, it’s hard to blame Clinton for rejecting Stern’s offer. But it reflects an overconfidence, one rooted in a disconnect with the truck drivers, contractors, and store owners Stern has known for years as his listeners.
It also speaks to the importance of Trump’s pop cultural cachet. Clinton could have the endorsements of every celebrity (and she almost did), but after Trump spent years in venues like Stern’s, she should have known that mattered, and had the respect for those voters to go into their spaces.
Let me rephrase that. Clinton thought it “mattered” but in a way that harmed Trump’s candidacy, assuming his freewheeling political incorrectness (a gentle way to describe some of his most quotable moments) was more of a liability, and to the point where it made her the obvious choice. With some persuadable voters, that was probably the case. With others, it either didn’t affect their decision or boosted Trump’s appeal.
There are many reasons the election went the way it did. Trump and Clinton’s relationships with Howard Stern are not the key to unlocking the Great Mystery of 2016. And Stern’s telling of his failed bid for a Clinton interview mostly emphasizes a dynamic we already understood. But with a large crop of Democratic hopefuls starting to jostle for the spotlight, it’s at least a timely reminder of an important lesson, and one it’s not clear most of Trump’s opponents have really learned.
