President Donald Trump listens to a reporter’s question aboard Air Force One en route from Florida to Joint Base Andrews, Maryland, January 4, 2026. REUTERS/Jonathan Ernst
President Donald Trump has found himself falling into the same trap of his own making over and over again throughout his career, his one-time biographer revealed, even before his entry into politics, but now, there is no guarantee that he will be able to escape it once again.
Michael Wolff is a longtime reporter and author with close connections to the Trump White House, best known for a series of tell-all books documenting his first term in office. During the latest episode of his Daily Beast podcast, "Inside Trump's Head," he observed how the president's entire professional life can be defined as a series of "predicaments" that he created for himself.
"I’ve seen him in the middle of the Russia investigation, in the middle when he fired... [former FBI Director James] Comey and everything seemed to be coming down on his head. I’ve seen him in the middle of COVID when he absolutely had no idea what to do," Wolff said "And, I’ve seen him in the middle of deciding... or believing that the election had been stolen from him."
He continued: "The truth is that Donald Trump’s entire... political career and maybe longer career has been a series of these predicaments — many of his own making— that he appeared not to be able to deal with, cope with or get out of. Now, the curious thing is that he has so often, in fact, gotten out of them."
Throughout all of this, Wolff noted that Trump has consistently avoided ever admitting his own failure, which is something that he attributed to his "remarkable" ability to deny reality and create his own world.
“How does he not fall on his sword and say, ‘I failed’? And the answer is, as it has always been in everything that he does, is this remarkable ability, this rhetoric and will to deny reality," Wolff explained. "And he has done that better than anybody else in so many situations. His entire life and persona is essentially that: ‘I am the world’s greatest businessman,’ where every piece of evidence suggests absolutely the opposite of that.”
During another recent episode, Wolff discussed the current predicament ensnaring Trump: his self-inflicted war with Iran, and his administration's inability to secure a peace and reopen the Strait of Hormuz. As he explained, staff within the White House "literally do not know what to do" to handle the situation at any level. In keeping with Trump's ability to ignore inconvenient realities, he also noted that Trump is insisting almost everyday that things are actually going well.