As explained by Rolling Stone, Stern called Trump before he became president a “fantastic” interview. He also called the then-business mogul “unguarded” during the many times on Stern’s radio show where they touched on many topics during their talks, including how to avoid AIDS, beauty, and how to treat women, per this Factbase transcript.
Stern continued to have Trump on as a guest throughout his campaign, although he noted that the current U.S. president became “one of the worst radio guests” despite their long friendship. Stern famously attended Trump’s wedding to Marla Maples and in turn, Trump attended Howard’s marriage to his wife, Beth Stern.
“I was at Mar-a-Lago around when it was announced that Donald was going to run for president,” Stern said to The New York Times. “And like everyone else, I thought, ‘Ha-ha-ha.’ So, knowing Donald, I can tell you with some assurance that I don’t believe that he thought anyone would buy in. Lo and behold, people did. But I’m pretty sure that there was no intention of actually being president.”
He also stated to the New York Times that he feels “Donald is caught up in getting the love of the masses, which is unobtainable and leads to no good.
Stern also noted that while he no longer attempts to be as controversial as he once was on-air, where he was given the nickname of “shock jock,” he is now a thoughtful interviewer who carefully considers each question he asks his guests.
He also revealed that he had a cancer scare to The New York Times, not elaborating on it, but rather admitting that he took one sick day off from work to deal with his issues back in 2017. The outlet added that Stern had an MRI that revealed a probably cancerous cyst. His surgery to have it removed caused him to cancel a show. It was the first time he had done that and the publication noted that he was criticized for doing so.
Stern makes a reported $90 million a year for his radio show and has admitted to supporting Hillary Clinton both in 2008 and 2016, despite his friendship with the business mogul-turned-president. According to MarketWatch, Stern and Trump have not spoken since Stern declined his invitation to speak at the Republican National Convention in 2016.
Howard Stern’s radio show can be heard daily on Sirius XM.