By David Canfield
May 13, 2019 at 11:00 AM EDT
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The following is an excerpt from Howard Stern Comes Again, the first book in over two decades from Howard Stern. In this selection, Stern reveals how close Hillary Clinton was to appearing on his radio show in the 2016 election, and why it didn’t happen. Read on below. Howard Stern Comes Again publishes Tuesday and is available for pre-order.

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.

As you know by now from reading this book, Donald Trump and I go way back, and had I endorsed him for president, publicly hitched myself to his candidacy and gone all in, who knows what might have come from it. Instead of writing this book, I might have been sitting on the Supreme Court. Chief Justice Stern. Imagine me in my custom John Varvatos robe, banging my gavel and picking the pubic hairs out of Clarence Thomas’s Coke can. Maybe I’d be chairman of the FCC, in charge of the government branch that tried to put me out of business. Think of the cosmic irony in that. Perhaps a cushy ambassadorship someplace warm, or at the very least I might have wrangled an invitation to Camp David.

But I’m no sellout. I have been a fan of Hillary for nearly as long as I’ve known Donald. This woman has dedicated her life to public service, and that’s what I look for in a candidate. She was a first lady, senator, secretary of state. Her entire life has been in the service of our country. People would say to me, “You’re just voting for her because she’s the lesser of two evils.” I’d say, “No, I wanted her as president before I wanted Barack Obama.” I love Barack Obama, but I was a Hillary Clinton supporter going all the way back to 2008. I think she would have been a great president.

I saw long before anyone else that it wasn’t going to be easy for her to beat Donald. I didn’t see her connecting. My audience spans the entire country, including the swing states. I know these people. 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. As I said in this book’s introduction, I consider Donald Trump one of the best radio guests ever. He just knows how to connect with an audience. Hillary does not.

I was talking to my agent, Don Buchwald, about this. I said, “If Hillary did the show, my listeners might appreciate her commitment to public service and her decency and humanity.”

Don immediately became obsessed with this idea. We both did. We wanted to do whatever we could to make it happen.

This wasn’t the first time we set our sights on a Moby Dick–type interview subject. In the early nineties, we tried to arrange an interview with Michael Jackson. He was looking to rehabilitate his image after the child molestation allegations, and his team reached out to us. They had the idea of me organizing some kind of rally in his honor in New York. I thought that was stupid and had my own idea of doing a TV sit-down with him at halftime during the Super Bowl. Don and I got as far as meeting Michael at his manager’s Central Park apartment. Michael walked in dressed in his full military getup and the tape on his nose. We talked for about ten minutes. I couldn’t stop staring at all the makeup on his face, which was practically dripping off. He was like the Elephant Man. After the meeting, we never heard from him again.

I knew I probably shouldn’t get my hopes up about Hillary. I couldn’t help it. I really believed that by coming on my show she would win over the type of voters she so desperately needed. I also thought my time on AGT might have made me more palatable in her eyes. I had been so astonished and humbled by how the American public had come to embrace me, thanks to that show. Often before we taped an episode, I would go out in front of the crowd and warm them up. I would tell the story of how in 1985 the chairman of NBC, Grant Tinker, had fired me from my radio show on WNBC and then said over his dead body would I ever be allowed back at the network. “Well,” I’d tell the crowd, “now Grant Tinker is dead, and guess what? Here I am at NBC.” They would laugh and applaud, and it felt like a victory lap—like Rocky running up the steps in Philadelphia. Sure, a less fit and muscular Rocky. I punch my own meat but not in a fridge. Still, I was on top of my game. Even if Hillary wasn’t a regular viewer of the show, maybe word would get back to her that it might be time to reconsider her opinion of me.

Thinking about the Michael Jackson Super Bowl idea and AGT, Don and I wondered if TV was the answer. Maybe Hillary would be more willing to do an interview on camera than on the radio. As fervently as I’ve championed the radio format throughout my career, I know there are still plenty of people who see TV as more desirable. There were a few big TV networks that had been after me to host an interview show. It wouldn’t be a regular thing, just a few specials. SiriusXM was cool with it, since it didn’t conflict with my radio show. But I’m very loyal to Sirius, and I wouldn’t consider doing one of these TV specials unless it was for a really big guest.

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The head of one of these networks was a huge financial backer of Hillary. Don went to him and said, “You get Hillary, and we’ll get equal time with Trump. Then you’ll get two specials.”

It would’ve been easy to get Trump for an interview. All throughout the campaign he had been reaching out to me. He even asked me to speak at the Republican National Convention. In my calculation, all I’d have to do is ask and he’d do it.

So this network honcho presents the idea to Hillary. And she says no.

This only makes Don more determined. He’s got a lot of connections of his own in the Democratic Party. Don went to them. He told them that we would even be willing to do a rehearsal before the show, so Hillary could see the line of questioning ahead of time. I wasn’t going to bring up Monica Lewinsky. The old me would have tried that. That would have been the first thing I said. Now I see how that could only be viewed as an attack. I wasn’t interested in that anyway. The interview would have been, “Who are you as a person? What makes you tick? Talk to me about your life as a young girl. What were your dreams? When did you first realize you wanted to be in politics?” I could have talked about her childhood for an hour. I wanted to get to know her as a human being. That Lewinsky stuff is pointless unless you get to know her first. Hearing her talk about the disappointments in her life? The audience would’ve fallen in love with her.

I’m telling you, I was obsessed with this. I was Captain Ahab. I wanted it more than anything. I did all this research on her and discovered she liked gardening. I ordered a huge gift basket of gardening supplies, thinking I’d send it to her to break the ice. The basket was enormous. There was all sorts of gardening crap in there, like packets of seeds.

Then I reconsidered. I thought that might be coming on a little strong. That’s not me. I don’t beg. What I did instead was agree to give an interview to the New York Times. They had contacted me a while before about doing a profile. I said no. I hate doing interviews. I hate being on the other side of the microphone. I told Don to tell them yes.

In July 2016, the Times ran a huge story in the Sunday paper about how my style had changed over the years. The headline couldn’t have been more perfect: “Confessor. Feminist. Adult. What the Hell Happened to Howard Stern?” Several celebrities were quoted saying what a great interviewer I was. Surely this would reassure Hillary about talking to me. I figured she reads the New York Times. Of course she does.

The article came out, and we heard nothing from her campaign. Then Don remembered this writer at the Washington Post who had been after him for a while about interviewing me. A few days after the Times story, another one dropped in the Post. This headline was even more direct: “Howard Stern Makes His Pitch: Why Hillary Clinton Should Do My Show.” If you look at that interview and the Times story, I’m basically telling her the plan. I don’t do that with guests, but I wanted her to know that she didn’t have to worry. She’d be in good hands. She could trust me.

The Post story came out. Again, we heard nothing from her.

Then I saw her in the debates. 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. I don’t want to sound arrogant.

I don’t want to say that I could’ve tipped the election. But how many votes did she actually lose by? In Michigan, Pennsylvania, Ohio, Florida—a couple thousand votes here, a couple thousand votes there. SiriusXM has thirty-three million subscribers in America. We consider each of these to represent at least two people, since households often share a subscription. Do the math. Because I can’t—multiplication isn’t my strong suit. I’m not saying all SiriusXM subscribers are Howard Stern listeners. But let’s just say that half are. Would that not have done something?

All it would have taken is for some guy to go, “You know, I work hard for a living. I drive a truck. I’m a contractor. I’m a store owner. I heard Hillary Clinton on the Howard Stern Show talking about her passion for people, and I was damn impressed.” Who knows what would have come out of our conversation. Some little story that people could identify with. I can’t tell you how many times I’ve done an interview where someone in my audience writes me and says, “I never cared about Lady Gaga.” Or, “I never listened to Sia.” Or, “I always hated Rosie O’Donnell.” And then they go, “But damn I love her now!”

To some people it wouldn’t have mattered what we talked about. Just the fact that she had the guts to show up might’ve done the trick.

So why didn’t she? I’ll tell you why. She was afraid. She got tight. She thought it was in the bag, and she thought, “I could go talk to Howard and really screw things up.” She thought it was a gamble. In my mind, the gamble was not coming on the show.

I was right. Had she done the show, it might’ve changed the election.

Becoming the first female president wasn’t the only thing Hillary missed out on. She also missed out on one badass gardening basket. I never sent it to her. For me to go to all that trouble, submit to those newspaper interviews—no way was I going to waste those seed packets on her. I divvied it up among my staff instead.

From HOWARD STERN COMES AGAIN by Howard Stern. Copyright (c) 2019 by One Twelve, Inc. Reprinted by permission of Simon & Schuster, Inc.

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