On with Kara Swisher
On with Kara Swisher

Maggie Haberman and Jonathan Swan Take Us Inside Trump’s ‘Imperial Presidency’

In their new book, “Regime Change,” New York Times journalists Maggie Haberman and Jonathan Swan take readers inside President Trump’s return to the White House in 2025 and the chaotic year that followed. It’s an incredibly revealing look at a president and an administration untethered from the hist

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Episode Summary

Executive Summary: Kara Swisher interviews Maggie Haberman and Jonathan Swan about their book on Trump’s second term, focusing on how his White House is more transactional, more corrupt, and more structurally untethered than term one. The conversation highlights tech CEOs’ embrace of Trump, Elon Musk’s rise and fall, AI’s rapid political ascent, and the family’s direct monetization of presidential power.

Main Topics: Trump’s second term as a radically different presidency (Priority: 5/5): Haberman and Swan argue term two is defined by fewer reliable sources, more secrecy, and a smaller inner circle, forcing them to discard most reporting and verify only what could be tightly corroborated. Tech CEOs, flattery, and power bargains (Priority: 5/5): The hosts discuss how major tech leaders shifted from skepticism to active accommodation, showing up publicly behind Trump and sending flattering messages while seeking relief from regulation and competition. AI as a sudden policy obsession (Priority: 4/5): A Trump campaign meeting with OpenAI executives transformed him from an AI skeptic into a booster, helping set a hands-off regulatory posture and making AI a central policy battleground. Elon Musk’s influence and collapse inside the administration (Priority: 5/5): Musk is portrayed as a quasi–co-president who hijacked parts of the government, drove aggressive cuts, and then fell out with Trump once he became a liability and overshadowed him. Direct monetization of the presidency (Priority: 5/5): The discussion stresses that Trump and his family are openly using the White House for business advantage through crypto, licensing, donations, and foreign ties, collapsing any separation between office and enrichment. 2028 succession, impeachment, and Trump’s legacy mode (Priority: 4/5): Trump seems less focused on the midterms than on legacy-building, keeping potential successors off-balance while signaling he may not run again, though he will remain the center of MAGA politics. Health secrecy and institutional erosion (Priority: 3/5): Trump’s medical status is described as a persistent black box, while the broader administration is said to have weakened norms around DOJ independence, oversight, and congressional checks.

Key Arguments: Haberman and Swan say they assumed sources were lying by default and only included scenes that could be verified from overlapping accounts and details. The book argues Trump’s second term is more chaotic and more powerful than the first because he returned with a plan, loyalists, and far less institutional resistance. Tech leaders embraced Trump not just out of fear, but because they disliked Biden-era regulation and saw Trump as a vehicle for deregulation and competitive advantage. Trump derives pleasure from public humiliation because it forces converts to prove loyalty, especially when he can display flattering texts and stage public displays of submission. The OpenAI meeting in 2024 was pivotal because it turned Trump from someone who feared AI into someone eager to help the industry by removing constraints. Elon Musk used immense money, attention, and access to become deeply embedded in the White House, but his visibility and overreach ultimately made him expendable. The Trump family’s business activity is portrayed as unprecedented because money can be directed straight into the family’s ventures without intermediaries. Democrats face a structural problem: aggressive accountability efforts can energize Trump’s coalition and unify a fractured Republican Party around him. Trump is focused on legacy, not governance in the traditional sense, using the presidency to rename, brand, and reshape institutions and history.

Data Points: Book reporting jettisoned: 99% - Haberman says most of their original reporting was discarded to keep only verifiable material for the book. Book focus window: First 14 months of Trump’s second term - The authors narrowed the scope to the early part of the second administration. Trump family business gains after return: At least $2 billion - Kara cites the reported amount the family made after Trump returned to office. Crypto share of gains: About half - Kara says roughly half of the $2 billion comes from the family’s cryptocurrency business. Elon Musk spending to elect Trump: Around $300 million - Swan says Musk and allies spent roughly this amount to help elect Trump in 2024. Office rent reference: $2,000 a night - Swan notes Elon Musk lived in a Mar-a-Lago cottage Trump usually rents at this rate. Howard Lutnick donation: $25 million - Haberman describes Lutnick’s donation to Trump’s presidential library and Trump’s bragging about it. AI commuting/late adoption: 2022 - Swan says Trump only started text messaging in 2022, illustrating how late he came to AI and digital tools. Era gap in AI: More than 20 years - Swan notes Trump adopted text messaging more than two decades after many others. Mar-a-Lago gift display: Printed flattering texts - Trump showed messages from Zuckerberg and Bezos to guests as trophies.

Pivotal Quotes: "He is the most consequential president, certainly of my lifetime, certainly of Jonathan's lifetime." — Kara Swisher: Opening framing of Trump’s historical significance and the book’s premise. "False until proven otherwise became my default setting in the first term as well." — Jonathan Swan: Explaining his reporting mindset and how trust has shrunk further in the second term. "Trump is a coin-operated president." — Kara Swisher: Kara’s characterization of Trump as openly transactional and monetized.

Implications: The conversation suggests a presidency where private enrichment, tech influence, and weakened oversight are becoming normalized. For listeners, the takeaway is that Trump’s second term is less about policy continuity than about power, loyalty, and marketable access.

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