Did Howard Stern regret any Trump interviews after 2016?
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Executive summary
Howard Stern never said he regretted having interviewed Donald Trump in the specific, personal way of offering an apology or calling those interviews a mistake; instead he repeatedly framed the material as part of a public, entertainment-driven archive he won’t exploit, said some Stern-era quotes were taken out of context, and placed his regrets on other interviews and on his broader earlier conduct [1] [2] [3]. Multiple interviews and profiles show Stern refusing to rebroadcast Trump clips, acknowledging the public focus on those conversations, and distinguishing regret about his own past behavior from explicit regret about hosting Trump [4] [5].
1. Stern refused to weaponize his Trump archive — not an admission of regret
When old Trump clips resurfaced in 2016, Stern announced he would not replay past Trump interviews and called doing so “a betrayal” of guests, arguing Trump had been “having fun” on the radio and that airing the tapes now would be inappropriate; that refusal was framed as a protective choice rather than a confession of regret about having hosted Trump [1] [4]. Stern told media he “fully knew what I was doing when I interviewed Trump,” and said the conversations were done publicly for entertainment, not secret moments to be mined — language that distances him from regret and instead stresses intent and context [6] [1].
2. Stern said some Trump quotes were taken out of context, and that felt unfair
In interviews after 2016 Stern pushed back on how journalists used his Trump interviews, telling Good Morning America he felt it was “unfair to Trump” when lines such as Trump’s “personal Vietnam” quip about STDs were treated as serious rather than joking radio banter, which is an argument about interpretation rather than an expression of remorse for airing the segments [2]. That defense is consistent with Stern’s long-standing view of his show as “locker-room” entertainment, and his public position was to contextualize rather than apologize for what aired [6].
3. He conceded the interviews had to be included in his book because of public attention
Stern later said he “had to include Donald Trump” in his book because so much attention had been paid to their conversations during and after the 2016 campaign, a practical editorial decision that again signals responsiveness to public interest rather than personal regret about hosting the interviews themselves [5] [7]. Stern has described his relationship with Trump as complicated — warm at times but soured after he declined to introduce Trump at the 2016 convention — but that complexity is presented as a personal fallout, not a public apology about past interviews [7] [8].
4. Stern’s explicit regrets have centered elsewhere — therapy, early excesses, and specific interviews
Across memoir excerpts and profiles, Stern identifies regrets about his earlier career excesses and names specific interviews — most notably a “meaningless, antagonistic” interview with Robin Williams — as his biggest regret, and he credits therapy for changing his perspective on past conduct; these public admissions show he does regret some earlier practices generally, but he has not singled out his Trump conversations as the core of that remorse [3] [7]. That separation matters: Stern admits remorse about his own narcissistic impulses and some guest treatment, yet he stopped short of saying the Trump interviews themselves were something he wished he’d never done.
5. Alternative readings and the implicit political dimension
Observers can reasonably read Stern’s refusal to rebroadcast Trump clips and his contextual defenses as de facto regret or at least a moral distancing, especially given Stern’s public support for Hillary Clinton in 2016 and later criticisms of Trump’s fitness for office, which altered their relationship from social acquaintances to political adversaries [4] [7] [8]. But the record in the cited reporting is clear: Stern’s words emphasize context, boundaries around replaying archival material, and regret about earlier journalistic style rather than an explicit statement that he regrets interviewing Trump per se [6] [2] [3].