Trump expert exposes how his team shields him after latest 'bombed' speech

President Donald Trump takes the lectern to deliver remarks at the WHCA Dinner at the Waldorf Astoria hotel in Washington, D.C., July 24, 2026. REUTERS/Jonathan Ernst

President Donald Trump will probably never hear the tough truth about his latest "bombed" speech, because according to his one-time biographer, his team has consistently done everything they can to protect his ego from reality.

Michael Wolff is a longtime author and reporter best known for his extensive coverage of Trump's political career, including several books about his tumultuous first term in the White House. In the latest episode of his Daily Beast podcast, "Inside Trump's Head," Wolff discussed Trump's speech at Friday evening's White House Correspondents' Dinner (WHCD) and claimed that his staff will almost certainly have told him "you were fantastic," despite how poorly the address went. In turn, Trump will almost certainly believe that he did great.

"I can tell you that he came off that stage, everybody said that 'you were fantastic,' and that's exactly what he will believe," Wolff told co-host Joanna Coles, after she suggested that Trump was aware that his speech had been a flop. "Donald Trump, I feel safe to say, has never once in his life even entertained the possibility that he has bombed."

Wolff further argued that Trump appeared "desperate" throughout the address as he continually flubbed jokes, but nonetheless, the former biographer suggested that he felt some level of "fondness" towards the president for his approach to the WHCD crowd.

“Sometimes I get something like almost a little flash of fondness, could it be for Donald Trump? I mean, I hate this White House Correspondents’ crowd,” Wolff told Coles. “I hate them for their self-satisfaction, for their shared references, for their shared jokes, for their profound lack of originality at any level. So the idea that Donald Trump would go in there and say, you know, ‘I basically I don’t give a s——t about you.’"

He added: “And the interesting thing is that so many other politicians and presidents certainly have tried to adapt to what the White House press corps wants, what the press wants. And Donald Trump, even in his symbiotic relationship with the press, has just never done that.”

Coles responded that Trump, despite his attacks on press freedom, "loves the press," largely because "He couldn’t exist without the press." Even with that being true, Wolff asserted that Trump "has never done what they want him to do."

"He has never become what they want him to be, which every other politician has,” Wolff explained. “I feel this is a somewhat awkward position to suddenly be defending Donald Trump... but, you know, he doesn’t grovel.”

Coles added: “He was flailing. We’ve said he feels desperate. You know, the White House is leaking. He’s stuck in a war he can’t do anything about. And he read like an old Catskill comedian who was on his last desperate material.”

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