Podcast Summary: To The Contrary with Charlie Sykes

Episode: Anne Applebaum: America’s Democratic Decay
Air Date: October 28, 2025
Host: Charlie Sykes
Guest: Anne Applebaum (The Atlantic, author of "Autocracy Inc.")

Episode Overview

This episode tackles the rapid decay of American democratic norms and institutions under the Trump administration, featuring an in-depth conversation between Charlie Sykes and renowned journalist Anne Applebaum. The discussion spans from current threats to election integrity and institutional kleptocracy to the cultural consequences of America’s shifting global image. Applebaum, speaking from Poland, offers comparative insights drawing from international examples of democratic backsliding, authoritarian consolidation, and public resistance.

Key Discussion Points & Insights

1. Speculation about a Trump “Third Term” and Institutional Fragility

Timestamp: 01:58 – 04:45

• Context: Discussion begins with Steve Bannon's recent claim that Trump could seek a third term.
• Applebaum’s Reaction: Dismisses Bannon’s comment as attention-seeking but highlights a more pressing concern: the vulnerability of U.S. institutions and the lack of political will within the GOP to constrain constitutional violations.
• Key Insight: The focus should be on immediate risks to the midterms and systemic gamesmanship, as “Americans lack imagination” for believing clear warning signs (“they will actually do what they say they're going to do”) are just political theater (02:38).

"My worry and my fear, where Americans lack imagination is I'm much more worried about the midterms and the various games that might be played to affect them." — Anne Applebaum [02:38]

2. Democratic Backsliding: Election Interference & Institutional Capture

Timestamp: 04:45 – 10:15

• Gerrymandering and Voter Restrictions:
  • The federal government is pressuring GOP-led states to increase gerrymandering in unprecedented open ways (04:45).
  • New federal demands for access to states’ voter rolls create openings for bad faith manipulation (05:22).
  • Additional voting barriers (e.g., requiring passports or birth certificates, complicating married women's registration) add new hurdles (06:30).
• Delegitimization Tactics:
  • Trump is seeding doubts about election outcomes, readying to contest results should Democrats win close races (07:18).
  • Fear of federal/militarized police intimidation at polling places, echoing Gov. Pritzker’s warnings (08:24).

"They're building a narrative that lots of illegal immigrants are voting... There's absolutely zero evidence of that." — Anne Applebaum [05:52]

3. The Normalization of Kleptocracy and Abuse of Office

Timestamp: 09:27 – 14:00

• Corruption as SOP:
  • Applebaum’s “Kleptocracy Tracker” documents rampant conflicts of interest, financial self-dealing, and using public policy for private gain.
  • The administration acts without fear of legal reprisal, showcasing new and dangerous precedent.

"This administration is the first that I can remember that doesn't act like anybody's ever going to investigate them or ever going to care." — Anne Applebaum [09:27]

• Supreme Court Implications:
  • Trump’s overconfidence is reinforced by broad Supreme Court immunity rulings, leading to unchecked executive action.
• Flooding the Zone:
  • The overwhelming volume and pace of scandals mean even major abuses no longer dislodge public focus or accountability.

"Their tactic is to violate the law and…commit these kleptocratic acts so quickly and in such fast succession that they aren't being held accountable." — Anne Applebaum [13:14]

4. Culture of Disdain and Authoritarian Playbook

Timestamp: 14:00 – 21:53

• Disdain for Opponents:
  • Discussion of Trump’s vulgar AI video depicting himself dumping excrement on protestors, symbolizing not just contempt but a sustained autocratic strategy to dehumanize critics (15:31).
  • Applebaum connects these tactics to autocrats globally — moving from silencing and violence to public shaming and humiliation as tools of repression.

"The attempt now is to make your opponents so unattractive, to mock them, to smear them... This seems to me that the Trump video was a continuation of that." — Anne Applebaum [15:31]

• Contrast with Overseas Protests:
  • U.S. reactions compared to large-scale Hungarian demonstrations against Orban, with Applebaum noting Americans may not have connected daily corruption to personal consequences — so anger has not yet peaked (20:04).

"Hungarians are much poorer than they should be because of the corruption in their country. And they've now made the connection... I don't know that Americans have made that link yet." — Anne Applebaum [21:33]

5. Rapid Authoritarian Consolidation

Timestamp: 21:53 – 24:24

• Comparative Speed:
  • Hungary’s Orban consolidated power over 15 years; in the U.S., Applebaum argues, “we’ve compressed 15 years of authoritarian drift into nine months” due to methodical study and deliberate action by Trump’s team (22:32).

"They weren't experimenting when they arrived in January... they were prepared in advance for, to carry this out." — Anne Applebaum [23:16]

• Urgency Before the Midterms:
  • The rush to entrench power comes from narrow electoral margins and the possibility of losing future elections (23:53).

6. The Bulldozing of Institutional Symbols and Press Complicity

Timestamp: 24:24 – 33:35

• Tearing Down the East Wing:
  • Symbolic attack on a shared national site, Trump’s unilateral demolition of the East Wing for personal gain represents disdain for tradition, history, and public ownership (25:03).
• Elite Enablement:
  • Financial and media elites, including the Washington Post/Jeff Bezos, condone and even praise this autocratic behavior, signaling the corrosive power of transactional loyalty and fear (28:31).
• Normalization of Autocracy:
  • Even famed American resistance to demagogues is not immune to “Caesar” appeal; “autocracy is the norm” historically, democracy the exception (30:50).

"People find autocracy appealing... the exception, historically, have always been democracies." — Anne Applebaum [31:47]

7. America’s Diminished Moral Example and Global Consequences

Timestamp: 33:35 – 38:56

• Loss of America as a Beacon:
  • Applebaum laments the rapid shift from America as a symbol of freedom and aid to one of “transactionalism and secrecy” (34:30).
• Global Reverberations:
  • Allies and adversaries alike feel the uncertainty; America’s withdrawal from leadership destabilizes world order, erodes trust, and may eventually have dire economic and security consequences even for Americans themselves (35:32).

"Almost everywhere I go, the one thing people want to talk about is what's happening in America and how will it affect us." — Anne Applebaum [35:36]

8. The Dangers of Hubris, Decision-Making in the Dark, and War as Diversion

Timestamp: 38:56 – 45:48

• Downsides of Authoritarian Rule:
  • Dense, loyalist circles around Trump mean policy is made without dissent or reliable data, paving the way for grave mistakes at home and abroad—e.g., botched Russia negotiations and impulsive economic or military actions (40:13).
• War as Political Tool:
  • Rumblings of war with Venezuela are discussed as a potential pretext for domestic crackdowns and emergency powers, with transactional motives (oil) also in play (42:40 – 45:48).

"I worry that their reasoning is that they want the US to be at war with somebody so that they have an excuse to declare an emergency..." — Anne Applebaum [44:20]

Notable Quotes & Memorable Moments

• On the normalization of unprecedented abuses:

  “Most of them [institutions], they failed... It’s a measure of how fragile things are that we can no longer count uncertainties.” — Charlie Sykes [04:20]

• On the loss of the U.S. moral example:

  “American culture is no longer synonymous with the aspiration to freedom, but with transactionalism and secrecy... The only Americans anyone can see are the ones trying to rip you off.” — Anne Applebaum [33:55] (as read by Sykes)

• On American complacency:

  “Maybe we have been broken out of our complacency. Maybe we had taken things for granted. We did think we were immune to history.” — Charlie Sykes [38:56]

Important Timestamps & Segments

• [01:58] - Applebaum opens with reflections on Bannon’s “third term” comment
• [04:45] - Applebaum details immediate threats to electoral integrity
• [09:27] - Discussing the administration’s lack of fear and unchecked kleptocracy
• [14:00] - Trump’s AI video and the culture of disdain/authoritarian strategies
• [21:53] - The rapid shift from democracy to authoritarianism: U.S. vs. Hungary
• [24:24] - Demolition of the East Wing and symbolic destruction
• [28:31] - Elite complicity and media praise as systemic enablers
• [33:35] - America’s global image: from beacon to cautionary tale
• [40:13] - Dangers of hubris: decision-making without oversight or information
• [42:40] - Venezuela as a case study in autocratic distraction

Tone, Style & Final Thoughts

This conversation is urgent, at times sobering, and rich in comparative history. Both Sykes and Applebaum are unsparing in their diagnosis of American democratic decay, drawing straight lines between American and global cases. The tone alternates between analytical and deeply concerned, with both speakers repeatedly stressing the importance of vigilance, imagination, and the risks of complacency. Applebaum’s international vantage point gives her warnings weight, often grounded in examples from Hungary, Poland, and Venezuela. The episode concludes with mutual concern for the future but also a reminder: “We are not the crazy ones.”