The Bulwark Podcast – Bill Kristol: March to Dictatorship (August 25, 2025)

Host: Tim Miller
Guest: Bill Kristol

Episode Overview

In this episode, Tim Miller interviews Bill Kristol on the current state of American democracy, arguing that the U.S. is not experiencing mere “democratic backsliding,” but is actively marching towards dictatorship. They break down recent troubling developments – military and law enforcement overreach, corporate extortion, political retribution, and a chilling conformity – while examining the Republican Party's silence and the strategic implications for democracy advocates. The episode is marked by historical analogies, present-day anxieties, and a call for resilience amid escalating authoritarianism.

Key Discussion Points & Insights

1. From "Backsliding" to "March Toward Dictatorship"

• Kristol’s Main Thesis (01:28–03:52):
  Bill Kristol critiques the use of “democratic backsliding” to describe America's plight, saying it’s more actively “a genuine purposeful march towards despotism, dictatorship.”

  “Authoritarianism seems a little too... too fancy and too nice almost... Authoritarian tendencies are in every society... but that doesn’t capture what Trump and his people are up to.”
  — Bill Kristol (03:35)

• On Eastern Europe vs. US:
  States that the term “backsliding” was apt for post-1989 Eastern Europe because of lingering authoritarian habits, but the US is witnessing deliberate choices leading toward dictatorship.

2. Militarization & Control of Law Enforcement

• Federal Takeover of Forces (04:22–07:32):
  Discussion covers Trump’s overt assertion of military authority in D.C., LA, with promises to expand similar tactics to Chicago, New York, Baltimore.

  "That's a pretty standard marker. That's not backsliding. That's Trump choosing to embrace an authoritarian and pre-dictatorial, as it were, method."
  — Bill Kristol (04:32)

• National Guard & State Rights:
  Trump’s actions undermine state control of the National Guard, eroding “the need for a well-regulated militia.”

• Comparison to Fascism:

  “It strikes me most of it actually is basically a giant ICE raid with some other stuff going on on the side... like a fascist play... playacting with ICE raids together.”
  — Kristol and Miller (07:08–07:32)

• Ludicrousness as a Weapon:
  Kristol draws from Mussolini and Hitler, noting that the clownish or “ludicrous” can coexist with danger.

  "Things can be ludicrous and dangerous at the same time... dictatorship becomes more entertaining."
  — Bill Kristol (08:29)

3. Purges & Retribution in Government and the Chilling Effect

• Military and Intelligence Firings (08:43–11:38):
  High-profile removals of dissenting military leaders (e.g., Lt. Gen. Jeff Cruz, Gen. David Alvin) signal not just retaliation but a systemic importation of loyalists.

  “Part of it is getting rid of people... who might offer an unbiased and honest opinion. They don't want that. But a lot of it is the message it sends to everyone else to shut up.”
  — Bill Kristol (10:38)

• John Bolton Raid as Show Investigation (11:38–15:21):
  The raid on John Bolton’s house demonstrates a campaign of intimidation against critics, especially high-credibility regime defectors.

  “He wants to punish Bolton. I don't think we should ever underestimate the retribution part of what Trump's doing... it has a real chilling effect.”
  — Bill Kristol (11:46)

• Broader Chilling Effects (16:02–17:32): The fear prevents potential critics, including officials, CEOs, and even entertainers, from speaking out.

4. Weaponizing Justice: Orchestrated Investigations

• JD Vance on Bolton and the DOJ (17:32–20:19): Vance openly embraces investigation as punishment, painting them as “neutral” but using process as deterrence and intimidation.

  “We're intimidating people. We're gonna intimidate you or investigate you. And maybe you won't be charged, maybe you will, but the punishment is the investigation.”
  — Tim Miller (18:57)

• Selective Use of Justice:
  Only critics are targeted. Allies, even if potentially complicit, face no such scrutiny.

5. Corporate Extortion and Precedents for Corruption

• Intel 10% Equity Case (22:55–26:35):
  The administration coerces Intel into handing a 10% equity stake to the government after Trump attacks the CEO, setting dangerous precedents for using state power for personal/political loyalty and financial gain.

  “You need to be nice to Trump or he's coming after your company... The price will be a fairly substantial chunk of change and obviously total silence and subservience for the next three and a half years.”
  — Bill Kristol (23:04)

• Implications for Business Community:
  Miller and Kristol note the contrast with past industry pushback (e.g., against Obama) and the total business community compliance now due to observable consequences for dissent.

• Long-Term Chilling Effects:
  Government capriciously turning loans/partnerships into forced equity stakes if a company’s CEO angers the White House.

6. Vindictive Immigration & Asylum Policy

• Case of Kilmar Abrego Garcia (27:52–33:17):
  The administration pushes for deportation to Uganda, a third country with which Garcia has no ties, as punishment for not pleading guilty, demonstrating both cruelty and transactional international deals.

  “It’s punitive and vindictive, to say the least.”
  — Bill Kristol (33:17)

• Behind-the-Scenes Deals:
  Miller and Kristol discuss possible quid pro quos with Uganda and other nations (tariffs, economic/trade arrangements), inseparably tying domestic cruelty to international black-box corruption.

7. Political Battles and Democratic Responses

• Maryland Governor Wes Moore Resists Militarization (33:30–39:45):
  Trump threatens to withhold disaster relief funding as political retribution; Moore responds with both political poise and sharp counterattacks.

  “...It would have been behavior that was resoundingly condemned in any other administration, almost impeachable.”
  — Tim Miller (34:35)

• Democratic Leadership Styles:
  Evaluating Moore’s “happy warrior” persona—visible, positive, but assertive in refusing to absorb Trump’s attacks unchallenged.

• Role of Never Trumpers in State Politics (41:12–43:44):
  Discussion of former Georgia Lt. Gov. Jeff Duncan considering a Democratic run for governor despite heterodox views, as a strategic model for expanding party coalitions—embraced more on state/local levels.

8. Israel-Gaza Conflict and Global Perceptions

• Concerns Over Israeli Tactics (44:00–49:38):
  The episode briefly shifts to discuss the humanitarian and strategic disaster of continued IDF strikes in Gaza, including attacks on hospitals and journalists.

  “It’s doing huge damage to support for Israel around the world... a real stain and... maybe an indelible one.”
  — Bill Kristol (45:32, 47:37)

• Lack of War Termination Strategy:
  Miller and Kristol question the logic and endgame, with “no clear alternate strategy,” defaulting into morally and politically costly conflict.

9. Transgender Ban in the Military: Discrimination and Strategy

• Conversation with Bri Farmer (49:38–52:04):
  Kristol recounts his conversation with Air Force Colonel Bri Farmer – her service story exposes the Trump administration’s renewed transgender ban as unambiguously discriminatory and counterproductive.

  “There’s no reason to do it, except if you want to just eliminate basically transgender people from... national life. You know, really is kind of a... totalitarian side of it is really horrifying.”
  — Bill Kristol (51:41)

• Importance of Speaking Out:
  Miller urges Democrats to highlight this injustice as both a moral and political imperative, noting the clarity of the issue compared to thornier trans rights debates.

Notable Quotes & Memorable Moments

• On the Absence of Republican Dissent:

  “I've heard almost no Republican voices objecting to any of this. It’s really kind of amazing.”
  — Bill Kristol (04:22)

• On Authoritarianism's Play-Acting:

  “Things can be ludicrous and dangerous at the same time.”
  — Bill Kristol (08:29)

• On Corporate Subjugation:

  “You need to be nice to Trump or he's coming after your company, and not in some complicated way...He's coming right at you and the price will be a fairly substantial chunk of change and obviously total silence and subservience for the next three and a half years.”
  — Bill Kristol (23:04)

• On Political Retaliation:

  “I'm not going to give money to Louisiana to rebuild after a hurricane because the governor said something mean about me on tv...”
  — Tim Miller (35:44)

• On Investigations as Punishment:

  “We're intimidating people... and maybe you won't be charged, maybe you will, but the punishment is the investigation.”
  — Tim Miller (18:57)

• On Transgender Ban:

  "There’s no reason to do it, except if you want to just eliminate basically transgender people from... national life."
  — Bill Kristol (51:41)

Timestamps of Important Segments

• Intro – 00:37–01:28: Bill’s “vacation” and news anxieties
• Defining the Crisis – 01:28–03:52: Backsliding vs. March to Dictatorship
• Law Enforcement & Military Overreach – 04:22–07:32
• The Danger-Farce Nexus – 07:32–08:43
• Military/Intelligence Purges – 08:43–11:38
• Bolton Raid & Chilling Effect – 11:38–17:32
• JD Vance & DOJ Weaponization – 17:32–20:19
• Corporate Extortion (Intel Case) – 22:55–26:35
• Immigration & Political Punishment – 27:52–33:17
• Wes Moore and Political Retaliation – 33:30–39:45
• Never Trumpers in State Races – 41:12–43:44
• Israel-Gaza Crisis – 44:00–49:38
• Transgender Military Ban – 49:38–52:04

Conclusion

This episode paints a stark, detailed portrait of America’s current lurch toward authoritarianism: a mixture of overt power grabs, intimidation, and systemic retaliation, with only subdued resistance from either opposition politicians or civil society. Kristol and Miller balance alarm with calls for resilience, strategic thinking, and determined opposition—whether in the media, politics, or personal engagement. The conversation is a sobering, necessary reality check condensed for the Bulwark’s “reality-based community.”