One thing is remarkably clear if you listen to The Howard Stern Show nowadays... he hates Donald Trump. Howard stands in total opposition to the vast majority of Trump's policies. He finds the man himself disgraceful. And he's publicly said that he 'despises' the people who voted for Trump, particulairly the ones who did it twice.
Despite all this, Trump has spent little to no time going after the self-proclaimed King Of All Media. Partly because the two have some supporters in common and Howard's influence over them remains nearly as strong as it was in the 1990s. But also because the two used to be friends. However, one moment ended this friendship forever...
Howard Stern Versus Donald Trump
There's no doubt that Donald Trump is a formidable political opponent. The former President continues to command unwavering support from his base who, in turn, force members of Congress and the senate who may not otherwise support him to bow to his every wish. The same goes for members of the right-wing media who need his supporters to stay in business. And for someone like radio legend Howard Stern, a lot could be lost from angering the Trump base... Yet, Howard does it all the time. He's made it clear... He loathes Trump's policies as much as the people who voted for him.
Without a doubt, Howard Stern remains Donald Trump's best opponent.
Howard's audience is more diverse than Trump's, after all it includes a lot of middle of the road and left-leaning individuals, and they are equally as loyal to him as Trump's base is to the now-disgraced former President. Sure, Howard's personal and creative evolution over the past two decades has lost him a few of his old-school fans, but he's still one of the most successful people in the entertainment buisness. His influence is far-reaching, which is one of the reasons why Donald Trump has spent almost no time attacking Howard publicly as he has with every other celebrity who has openly criticized him.
But part of the reason why Trump hasn't gone after Howard has to do with their history as friends.
Although, accoridng to Howard, the pair were more 'friendly' than 'friends'.
Trump was a common guest on The Howard Stern Show in the 1990s and early 2000s. Most of these interviews have gone on to be somewhat notorious. Howard even republished some of them in his excellent 2019 book, "Howard Stern Comes Again".
Because of Trump's numerous appearances on the show, as well as continuously bumping into one another at elite New York events, the two struck up a very positive connection. They were spotted sitting next to each other at a basketball game, Howard and his wife Beth flew down to Mar-a-Lago, and even included Donald and Melania at their wedding. Of course, this was a reciprocation of being invited to Donald and Melania's 2005 wedding which Bill and Hillary Clinton also attended.
But when Trump announced his presidential candidacy and started making highly controversial comments on the campaign trail, Howard's opinion of the man changed substantially. And things came to a head on one phone call.
The Phone Call That Destroyed Howard And Trump's Relationship
Even though Howard started to publicly condemning some of Trump's ideas as soon as he announced his presidential bid, he didn't start to really bash him until after a phone call prior to the Republician National Convention.
Prior to winning his party's nomination, Donald Trump even phoned in to The Howard Stern Show to attempt to campaign. But once Trump realized that Howard wasn't going to vote for him, Trump never went on The Stern Show nor ever spoke to Howard again.
And this was sparked by a phone call between the two of them.
While promoting "Howard Stern Comes Again" in 2019, Howard shared details about his final conversation with Donald Trump. He did this in his book, on talk shows, and on his own show. And each time he explained different aspects of the call.
To sum it all up, Trump phoned Howard to ask him to speak on his behalf at the Republican National Convention. Trump has always been interested in Hollywood and being a celebrity, and he did everything he could to get celebrity endorsements at the RNC... But he basically got none.
However, had he gotten Howard Stern, there's no doubt the RNC would have been a concert.
Despite Howard having some Libertarian leanings and a past of voting for both Republicans and Democrats, there was just no way that he was going to endorse Trump. In fact, Howard had always been a fan of Hillary Clinton and made that clear to Trump (who, ironically, had also been an endorser of Clinton before his presidential bid).
According to Howard, Trump did not take this well but remained polite as he hung up on him.
Afterwhich, the two had absolutely zero contact with one another.
Despite continuous criticisms, Donald Trump hasn't bashed Howard Stern. Could he be afraid of Howard's influence on some of his voters? Maybe it's because Howard knows private things about him that he wouldn't want public? Or maybe it's because they had a legitimately positive relationship before that call?
We'll never know. But we do know that these two are likely never to find common ground again.