Howard Stern said his relationship with Donald Trump effectively ended during the 2016 presidential campaign. Trump asked Stern to speak on his behalf at the Republican National Convention, but Stern declined because he supported Hillary Clinton. In 2019, Stern said he had also refused Trump’s request for an endorsement and had not heard from him since.
What caused Stern and Trump to fall out?
In his account, the break came down to politics and a specific request. Trump wanted Stern to endorse him and speak for him at the 2016 Republican National Convention. Stern said his support was with Clinton, so he would not do it.
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The Washington Post reported Stern’s recollection of telling Trump, “Donald, that’s not where my heart lies.” In a CBS interview preview published May 9, 2019, Stern described the endorsement request more directly: “I can’t endorse you.” The Washington Post’s 2019 account and CBS’s interview preview both report Stern’s explanation.
When did they stop speaking?
Stern placed the end of their contact after his refusal during the 2016 campaign. In the CBS preview, he said, “And I haven’t heard from him since. … We don’t talk at all.” That is Stern’s retrospective account, given in 2019; it does not establish the private terms of their relationship beyond what he said publicly.
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They had a long professional history
Trump had appeared on Stern’s programs many times before the political split. Roll Call’s archive project verified 35 Trump interviews spanning May 8, 1993, to August 25, 2015. Roll Call noted that records from before 1997 are difficult to establish definitively, so the count reflects its verified archive rather than a claim that no other appearances occurred. Roll Call’s interview archive documents its methodology and date range.
A recurring guest-host relationship is evidence of a long professional connection, but it does not by itself establish the private nature or emotional depth of a friendship. Stern’s own public explanation is the clearest basis for describing why contact stopped.
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How the later public disputes fit
Trump’s criticism of Stern after Stern interviewed Kamala Harris in 2024 was a later confrontation, not the original break Stern described. A 2025 Daily Beast account revisited the tension and Stern’s earlier explanation. The Daily Beast’s 2025 report covers that later period.
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