Inside Trump's Head

Episode: I Know Why Trump's Presidency Is Doomed: Wolff
Date: March 18, 2026
Hosts: Michael Wolff and Joanna Coles
Podcast by: The Daily Beast

Episode Overview

This episode offers a deep dive into the mounting chaos of Donald Trump’s second term, as interpreted by his biographer Michael Wolff and media veteran Joanna Coles. The discussion centers on the unraveling of Trump’s administration in the face of the Iran war, cabinet shakeups, and a presidency beset by both internal and external contradictions. With trademark candor and wit, Wolff and Coles explore Trump's psyche, decision-making, and the ripple effects throughout the Republican Party, highlighting how Trump’s character may ultimately doom his presidency.

Key Discussion Points & Insights

1. The War in Iran: Unintended Consequences and Trump's Mindset

[01:02–07:39]

• Michael opens with a bleak outlook: "The wheels are coming off... We're going to go from a political crisis to a political catastrophe. We're getting to the point because it's the second term in which he's not going to be able to recover." (02:01)
• Discussion of Joe Kent's resignation from a top counterterrorism role, citing disillusionment with the war’s rationale (Israel’s influence, failed promises to avoid endless wars).
• Michael comments on divisions within MAGA and the "right-wing, fundamentally anti-Semitic" drift.
• Trump's focus is singular: "So I think inside his head it's like, I'm bombing, I'm bombing, I'm blowing up, I'm obliterating. What more do you want from me?" (04:30)
• The fixation on "obliteration" and a binary view: Yes, we can destroy Iran’s military, but not the regime: "We have obliterated everything, but we'll continue to obliterate more." (06:21)
• Coles notes Trump’s surprise at the Iranian counterattack: “He seems completely blindsided by the fact that Iran would have any kind of response." (07:58)
• Wolff on Trump’s transparency: "It is part of his odd, shall we say, charm, that he is a transparent person." (09:11)

2. Trump’s Relationship with Truth and Self-Mythologizing

[12:34–15:57]

• Trump claims a former president wished they’d done what he’s doing in Iran—though no ex-president backs this up.
• Joanna: “...all the ex-presidents have come out and said that none of them have talked to him about this. None of them have said this. So he's just in his own world. He would like a president to have said this to him.” (13:57)
• Wolff breaks down Trump’s logic: "In Trump's mind... therefore they would have obliterated them if they had the guts to do the obliteration. But they didn't. But he does." (15:04)
• The hosts mockingly suggest Trump envisions secret talks with past presidents—or even George Washington—validating his actions.

3. Escalating Political Peril: The No-Win War

[17:11–20:46]

• Wolff summarizes Trump’s predicament: "He can't stay in Iran because oil is going crazy... But at the same time, he can't get out... The regime is not only going to stay in place, but... become more oppressive." (17:11)
• If he leaves, Democrats will attack him for a failed, pointless war.
• “He can't stay because those problems will increase almost on a geometric basis.” (18:40)
• Does Trump panic? Michael: "No, he doesn’t... he is always right. I mean, panic comes because you realize, oh my God, I might not be right... That never occurs to him." (20:02)

4. Cabinet Turmoil: The Blame Game

[25:38–32:46]

• Trump begins sacking officials—Kristi Noem, Rick Grenell—and might target RFK Jr. over the vaccine issue.
• Wolff: “The need to blame, not for any specific reason, but... if he doesn’t blame someone, the blame might come to him.” (30:02)
• The conversation probes Trump’s visceral, often irrational method of deciding who to blame and fire.

On RFK Jr.:

• Michael predicts, “I think he’s gonna get fired [before the midterms]…all the numbers are showing him to be a clear liability. The anti-vax thing is not a winning position.” (41:13-42:00)
• RFK Jr.'s utility was to peel away anti-Biden/anti-Trump voters, but Kamala Harris’s candidacy undercut that.

5. Civil War Within the Right / Marco Rubio, MAGA, and Neocons

[20:46–25:38]

• Marco Rubio seen as pushing Trump into a hardline neocon position: “Donald Trump is playing the Marco Rubio part... Marco Rubio is an obliterator.” (21:03)
• Coles presses on whether Rubio’s strategy is viable, suggesting the war is hardening the Iranian regime, not weakening it.
• Wolff discusses the lack of self-reflection among neocons and Trump alike: “Nobody ever realizes. I mean, Donald Trump certainly doesn’t realize he’s wrong...” (22:31)
• Wolff: “We’re at a contradiction on the right, we’re in a contradiction in how the American establishment has for so long seen things. We're in a contradiction within the close circle of Trump support.” (24:12)

6. Attacks on Gavin Newsom and Projections of Trump’s Own Issues

[31:17–36:46]

• Trump goes after Gavin Newsom’s dyslexia to distract and reposition the narrative:
  • Trump (via impersonator): "Honestly, I'm all for people with learning disabilities, but not for my president." (31:50)
• Joanna notes the irony: “From a president who clearly has all sorts of learning issues. You can’t fault the irony.” (32:46)
• Wolff recounts White House concerns over whether Trump is illiterate or dyslexic.
• Joanna: “There’s no question that Trump is voraciously unread.” (35:14)
• Michael: “Tony Schwartz wrote the Art of the Deal...often wondered if Donald Trump ever read the Art of the Deal.” (36:15)

7. The Role of Suzy Wiles and White House Stability

[37:15–40:43]

• Suzy Wiles’ illness is discussed; her absence is likely to destabilize the thin order in the White House.
• "She doesn't really fit into the Trump orbit... and the very fact that she is not of the Trump piece has allowed her... to hold this White House together." (39:05–39:36)
• Commentary on how she’s resisted the “MAGA makeover,” symbolizing both her uniqueness and fragility in the Trump world.

8. Jared Kushner's Expanding Influence and Financial Moves

[48:59–52:50]

• Michael: “He is the son-in-law who ate the father-in-law... He is the chief advisor and the chief negotiator on all things, well, on so many foreign policy things, but certainly on all things in the Middle East.” (49:16–50:00)
• Jared has leveraged his time in the White House to raise billions for personal investment funds, with possible policy implications.

Notable Quotes & Memorable Moments (with Timestamps)

• “The wheels are coming off... We're going from a political crisis to a political catastrophe.” – Michael Wolff (02:01)
• “Inside his head, it’s like: I’m bombing, I’m bombing, I’m obliterating. What more do you want from me?” – Michael Wolff (04:30)
• “Oh, my God. We didn’t expect them to fire back. How can they fire back when we’re obliterating them?” – Michael Wolff (09:11)
• “He can’t stay in Iran... but at the same time, he can’t get out... only worse things will happen.” – Michael Wolff (17:11)
• “He doesn’t panic per se... from his point of view, he is always right.” – Michael Wolff (20:02)
• “Blame—The need to blame, not for any specific reason, but because if he doesn’t blame someone, the blame might come to him.” – Michael Wolff (30:02)
• "I think inside his head it’s like, I’m bombing, I’m bombing, I’m blowing up, I’m obliterating. What more do you want from me?" – Michael Wolff (04:30)
• “Honestly, I'm all for people with learning disabilities, but not for my president.” – Trump (impersonator/clip) (31:50)
• “There’s no question that Trump is voraciously unread.” – Joanna Coles (35:14)
• "Tony Schwartz wrote the Art of the Deal... often wondered if Donald Trump ever read the Art of the Deal." – Michael Wolff (36:15)
• “He is the son-in-law who ate the father-in-law.” – Michael Wolff, on Jared Kushner (49:52)

Timestamps for Important Segments

• [01:02] The crisis of Trump’s second term, Iran war context
• [02:51] Joe Kent resignation & schisms in MAGA
• [04:30] Trump’s “obliteration” mindset
• [09:11] Trump’s view of war and reactions, transparency
• [12:34] Trump’s invention of ex-presidents supporting him
• [17:11] Trump’s political catch-22 over the Iran war
• [20:02] On Trump’s inability to panic or self-doubt
• [25:38] On the blame-shifting and firings beginning
• [31:50] Trump attacks Newsom over dyslexia (clip)
• [35:14] Trump’s alleged unreadness and literacy questions
• [37:15] Suzy Wiles’ pivotal role and recent illness
• [41:13] RFK Jr.’s looming sacking and role in the administration
• [48:59] Jared Kushner’s extraordinary influence and financial power

Takeaways for New Listeners

• Trump’s pattern is to reduce politics and foreign policy to a personal, visceral logic, often tangled in self-justification and a need for visible “wins.”
• The administration is internally fractured, with loyalty, ideology, and opportunism jostling for dominance.
• Trump’s inability to recognize flaws in his own strategy may spell disaster, as advised and enabled by a colorful, diverse, but ultimately unstable cast.
• Key cabinet and staff roles are vulnerable as blame increasingly becomes Trump’s escape valve.
• Jared Kushner’s influence continues to be enormous—and lucrative—while Suzy Wiles’ health may remove a rare source of order from the West Wing.

For anyone observing the Trump presidency through this podcast, the portrait painted is one of high-stakes, isolationist bravado, and an administration caught in a trap of its own making—a cycle fueled by stubbornness, projection, and a fixation on personal vindication above all.