Publish date: 2023-12-30

In his combination memoir and book of interviews released earlier this year, Howard Stern lamented the one guest he regrets never being able to book.

“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,” Stern wrote, positing that if his listeners had gotten the chance to hear her through his show, she may have actually beaten Donald Trump.

“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,” he added. 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.” 

More than three years later, Stern finally got his wish on Wednesday when Clinton made her first-ever appearance on his SiriusXM show to promote The Book of Gutsy Women, her new collaboration with daughter Chelsea. 

She admitted in the interview that she may have made a “miscalculation” when it came to her campaign press strategy, especially given that Trump had a “constant presence” on television. “I often did not prioritize media the way I should have,” she told Stern. 

When he was trying to get her on the show in 2016, Stern promised that he wouldn’t lead with questions about Monica Lewinsky. “The old me would have tried that. That would have been the first thing I said,” he wrote. “Now I see how that could only be viewed as an attack.” 

And yet he still managed to end up in some classic “Howard Stern” territory with the former secretary of state. 

During a conversation about the man she dated before she “hooked up” with Bill, Clinton started talking about how “handsome” her old flame was. “He looked like a Greek god,” she said to Stern’s delight. “He was very attractive.” 

“Well, contrary to what you may hear, I actually like men,” Clinton added, cracking up Stern’s sidekick Robin Quivers. 

This set Stern off down a path that was more in line with the “old” him. “Raise your right hand, you’ve never had a lesbian affair?” he asked. 

“Never, never, never!” Clinton exclaimed. “Never even been tempted, thank you very much.” 

“Unbelievable,” Stern marveled. In the end, he was right. He was able to get something out of his guest that she had never expressed before. 

Elsewhere in the interview, Stern also got Clinton to open up more about her 2016 primary contest with Bernie Sanders than she has in the past.

Asked if she was “upset” with how long it took Sanders to endorse her after she won the Democratic nomination, Clinton answered, “No, disappointed. And I hope he doesn't do it again to whoever gets the nomination.” She added, “Once is enough. We have to join forces.” 

“Bernie could've endorsed you quicker,” Stern said.

“He could've,” Clinton agreed. “He hurt me. There's no doubt about it, he hurt me.”

Stern also wanted to know why Clinton has remained in the spotlight as much as she has over the past few years. “Do you ever just want to lay in bed and say fuck this?” he asked. “‘I'm going to go into full seclusion and they'll never hear from me again.’” 

“First of all, that would only delight my adversaries, so I would never do that,” she replied.

If she had lost the election to a “normal Republican,” Clinton said, “I would've been unhappy, but I wouldn't have had that pit in my stomach, like, ‘What the heck? What's going to happen? What's he going to do next?’ His impulsiveness, his vindictiveness. Where does this lead?” 

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