Pod Save America – "Why is Big Business Caving to Trump?"

Guest: Andrew Ross Sorkin (CNBC host, New York Times columnist, author of 1929)
Host: John Lovett
Date: October 19, 2025

Episode Overview

In this episode, John Lovett sits down with Andrew Ross Sorkin to discuss the troubling trend of big business leaders kowtowing to Donald Trump, drawing historical parallels to the 1920s and 1930s. The conversation draws on Sorkin’s new book, 1929, both to highlight how bubbles and capitalist excess can upend economies and to examine the psychology and morality of America’s elite. Also discussed: the dangers of deregulation, the evolving American Dream, AI and crypto market speculation, and whether CEOs (like Apple’s Tim Cook) are making pragmatic or cowardly choices in their dealings with Trump.

Key Discussion Points & Insights

1. Speculative Bubbles: Then and Now

[03:02–07:49]

• 1920s Bubble Dynamics: Ordinary Americans speculated on stocks for the first time, fueled by easy credit from banks, with brokerages cropping up “on the corners of streets like Starbucks.”
  • “Everybody’s watching the market go up... If so and so is making all this money, I should be making the money too.” – Sorkin [03:24]
• The Cassandra of the Era: Senator Carter Glass, despite being an ardent segregationist, warned of “Mitchellism”—excessive speculation led by Charles Mitchell and National City Bank (Citigroup precursor).
• Democratization or Danger? Market access was seen as “a moral good,” democratizing finance. Groucho Marx famously played the market and lost his home.
• Modern Parallels: Sorkin sees echoes in today’s rush for crypto and SPACs, with decreased guardrails and fraudsters emerging whenever regulation loosens.
  • “Speculation is almost like the twin of innovation…but you need to do it in a way where it’s not toxic.” – Sorkin [06:10]

2. Trump, Crypto, and Deregulation

[07:49–11:55]

• Trump’s Flip and Capture: Trump’s embrace of crypto is depicted as transactional, stemming from support and donations by the crypto world.
  • “Trump’s flip on crypto was almost 100% related to the fact that the entire crypto community decided to effectively back his campaign and buy him.” – Sorkin [08:46]
• Debanking & Ties with Crypto: Post-January 6, the Trumps leaned into crypto due to being “debanked,” as mainstream banks sought to restrict their business.
• The "Genius Act": Current moves to allow risky, opaque assets into Americans’ retirement accounts; $12 trillion in retirement funds could be exposed to VC, private equity, and crypto investments.
  • “The charlatans and the frauds emerge in those worlds. The valuations are effectively made up.” – Sorkin [10:42]

3. Presidential Power & the Morality of Crisis Response

[13:59–23:00]

• Bank Holiday Standoff: Hoover refused to declare a bank holiday before FDR’s inauguration, partly due to image and ego, and partly over doubts about presidential authority.
  • “Hoover knew that the second [FDR] got into the White House… he would get the credit for it. And he does.” – Sorkin [15:01]
• Authority and Precedent: FDR’s willingness to use seldom-invoked statutes (Trading with the Enemy Act) redefined the presidency.
  • “There might have been some kind of project behind the scenes to think through what were the levers a president could pull that hadn’t been pulled before.” – Sorkin [20:52]
• Comparing Trump & FDR on Power: FDR’s expansion of executive authority is remembered positively because “they worked,” were not self-enriching, and “the public believed he was doing this at their behest”—unlike Trump’s self-dealing style.

4. The National Mood, Communication, & Parallels to the Present

[28:19–32:51]

• Crisis as Mood vs. Reality: Hoover kept framing the Depression as a crisis of confidence—a disastrous communications error. Biden and Trump, similarly, have both failed to credibly address perceptions of the economy.
• The ‘It’ Factor: Hoover’s lack of charisma crippled his ability to lead (unlike Roosevelt), a parallel Lovett draws to Biden’s struggles with messaging.
  • “He was a terrible orator. Whatever you think the it factor is in politics, he did not have it.” – Sorkin [29:21]
• Narrative Power: Lovett and Sorkin agree that great stories and leadership let people find their own meaning; explicit moralizing can be less resonant.

5. Tariffs & Market Psychology Under Trump

[33:19–39:20]

• Tariff Policy as “Vibes-Based”: Trump’s erratic tariff decisions move markets wildly, but markets (and investors) remain “professional optimists.”
  • “I’m no longer surprised. The investor class… are effectively professional optimists.” – Sorkin [33:59]
• Markets as the Only Governor: Markets’ negative reactions are sometimes the only thing moderating Trump’s behavior.
  • “The only governor thus far actually on this presidency has been the markets, weirdly enough.” – Sorkin [34:55]
• Tariffs = Leverage, Not Strategy: For Trump, tariffs and threats are simply about gaining leverage—considering alliances “transactional” and viewing the world as a board for “chess pieces.”
  • “The through line in my reporting about Trump is simply leverage… It’s not about relationships, it’s always going to be transactional.” – Sorkin [36:33]

6. Business Capitulation & Collective Action

[39:20–62:04]

• 1929 Parallels to Now: In both periods, elite wrongdoing is often rationalized as “what anyone would have done,” and major reforms are hijacked by industry (e.g., Glass-Steagall written partly by Rockefeller’s son-in-law).
• Modern CEOs Facing Trump (Tim Cook Example):
  • CEOs weigh tradeoffs: Speak out and gain nothing, or oppose Trump and get “slaughtered.” Most go along to protect business interests, hoping to outlast the current regime.
    • “If I raise my hand and say there’s a problem, I will be slaughtered... It’s like a mafiosa thing.” – Sorkin [57:24]
• Fear Stifling Dissent: Business leaders privately convey fear of Trump’s retaliation and lack confidence that dissent would matter unless done collectively.
• Red Line Uncertainty: Some executives propose writing down what their red line is so it doesn’t keep moving.
  • “The line you thought nobody would cross seems to get crossed almost every day and we become to some degree a nerd to what’s happening.” – Sorkin [61:29]
• Why No Countervailing Pressure: CEOs aren’t afraid of Democratic retaliation since it has little precedent and rare follow-through.
• Mamdani’s Rise in NYC: Business elite uneasy about Zoran Mamdani potentially becoming mayor, but start cozying up to him as his candidacy grows more likely.

7. The American Dream and Economic Morality

[46:37–55:32]

• Shifting Ideals: The American Dream morphed in the 1920s from modest upward mobility (Horatio Alger) to lotto-ticket wealth pursuits. This persists today, with the lottery-ticket mentality dominant in social media culture.
  • “The dream shifted… it became about the lottery ticket. It wasn’t just about having a better life than your parents, it was about reaching for the stars in this other way.” – Sorkin [47:56]
• Nostalgia for the 1950s Dream: Post-WWII utopia, with its homeownership and stable unions, is explained not just by policy, but by America’s monopoly position after the war, per Sorkin—a controversial take.
  • “We were not competing with anybody. We were it. We were the entire game.” – Sorkin [52:16]
• Tariffs & Globalization: U.S. car industry’s future hinges on protective tariffs against cheaper, potentially higher-quality imports from China. Sorkin relays: “Most Americans are going to spend more for less quality cars than much of the rest of the world is likely to get…maybe we should be cool with that, maybe we shouldn’t.” [54:38]

8. Warnings About AI, Crypto & the Next Crash

[66:24–68:14]

• Humility and Resilience: Sorkin ends by highlighting the need for humility, not just “resilience,” in the face of economic cycle risks.
• Obvious Risks Hiding in Plain Sight: He warns current speculative fervor in AI and crypto, and the migration of risky assets into retirement accounts, may be seen as glaring errors by future generations.
  • “Look at companies that don’t have enough money, are not making any money…making massive commitments…on a hope and a prayer and a dream that this will be the future. Some of them will be Amazon, but a lot won’t be. And we will look around and we will say, that was a mistake.” – Sorkin [67:16]

Notable Quotes & Memorable Moments

• “Speculation is almost like the twin of innovation… but you need to do it in a way where it’s not toxic.” — Sorkin [06:10]
• “Trump’s flip on crypto was almost 100% related to the fact that the entire crypto community decided to effectively back his campaign and buy him.” — Sorkin [08:46]
• “The only governor thus far actually on this presidency has been the markets, weirdly enough.” — Sorkin [34:55]
• “If I raise my hand and say there’s a problem, I will be slaughtered. That’s where we are. It’s like a mafiosa thing.” — Sorkin [57:24]
• “The dream shifted… it became about the lottery ticket.” — Sorkin [47:56]
• “It almost doesn’t matter how much money you have in your bank account or what’s on your business card; emotionally you’re still in that scared place.” — Sorkin [59:21]
• “Write down what are the parameters and the metrics with which you would actually [raise the red flag]. Because what keeps happening is the line you thought nobody would cross seems to get crossed almost every day…” — Sorkin [61:29]
• “Look at companies that…are making massive commitments to buy data centers…on a hope and a prayer and a dream that this will be the future. Some of them will be Amazon, but a lot won’t be. And we will look around and say, that was a mistake.” — Sorkin [67:16]

Key Timestamps

• [03:02] – Parallels between the 1920s bubble and today’s speculative booms
• [07:49] – Trump’s transactional adoption of crypto and the risks of deregulation
• [13:59] – Hoover, FDR, and the struggle over declaring a bank holiday
• [20:23] – FDR’s use of executive power, historical context vs. today
• [28:19] – The “national mood,” crisis leadership, and communication
• [33:19] – Trump’s tariffs, market “vibes,” and the political psychology of investors
• [39:20] – Historical corruption of reform (Glass-Steagall), CEO capitulation today
• [56:10] – Tim Cook & the dilemma facing modern CEOs in Trump’s America
• [61:15] – Red lines, collective inaction, and business leaders’ fears
• [66:39] – Final thoughts on speculation, humility, and the next possible crash

Conclusion

Through lively, candid conversation, Lovett and Sorkin trace America’s repeated cycles of economic speculation, crisis, and elite complicity—from the Roaring Twenties to the crypto-chaos of today. Sorkin’s historical insights and journalistic perspective highlight both the perennial flaws in American capitalism and the difficulties facing contemporary business leaders caught between self-preservation and civic duty under Trump. The episode warns listeners to mind the red flags of speculative excess—and to remember that, as in 1929, the warning signs are easy to see… in retrospect.