Podcast Summary: "The ACLU's War Against Trump"

Podcast: Hasan Minhaj Doesn’t Know
Host: Hasan Minhaj (186k Films)
Guest: Anthony Romero, Executive Director of the ACLU
Date: November 19, 2025

Episode Overview

In this episode, Hasan Minhaj sits down with Anthony Romero, the long-serving Executive Director of the ACLU, for an engaging conversation about the organization's historic and current battles to defend civil liberties—especially in the Trump era. Minhaj and Romero touch on questions of free speech, the nonpartisan nature of the ACLU, landmark legal strategies, and the fight against presidential overreach. They also dig into Supreme Court dynamics, strategies for defending rights in a polarized America, and Romero's personal view as a barrier-breaking leader.

Key Discussion Points & Insights

1. The ACLU’s Mission and Approach

• Protecting Rights for All:
  • The ACLU is committed to defending civil liberties, regardless of political affiliation or the popularity of the client.
  • "We represent the people's interests, the rights of individuals who come to us if they encounter some injustice... We do it for free. We don't charge any of our clients any money." — Anthony Romero (03:53)
• Long Game Litigation:
  • Cases often take years and go through multiple courts before reaching the Supreme Court.
  • "You have to play the long game. We map it out... You want to make sure you put multiple irons in the fire because you’re not sure how far it’s going to go." — Anthony Romero (06:04)

2. Nonpartisanship and Principle Over Politics

• Despite public perception, the ACLU pursues civil liberties irrespective of partisan considerations, sometimes representing deeply unpopular groups (NRA, KKK, neo-Nazis) to protect foundational rights.

• "If we ever become the civil liberties wing of the Democratic Party, we're dead... There is zero potency in a civil liberties agenda that doesn’t try to span across the political spectrum." — Anthony Romero (08:07)

• Memorable Moment: Romero describes representing the NRA against NY Governor Cuomo not for their gun policies, but for the principle of the First Amendment (09:22).

  • "We don't align with the NRA on gun policy issues. But the governor...was saying if you do business with the NRA, I’m going to cut business ties with you. And the NRA had a case...we took it. We represented the NRA for free... And we won." — Anthony Romero

3. Holding All Power to Account

• The ACLU scrutinizes all administrations—Democrat and Republican—on civil liberties.

• They challenged Obama on surveillance and drone policy and Bush on torture and Guantanamo.

• Despite differences in policy, "presidents are going to president; state power will always protect itself" (06:56).

• Hasan’s Challenge:

  • "Do you miss George W. Bush?"
  • Romero: “Who knew how bad it could get? ... The George Bush years...the idea of torture, of rendition, Guantanamo... But we have an administration now that’s gone way further.” (10:25)

4. Supreme Court Dynamics & Legal Realism

• Romero emphasizes not "writing off" the Supreme Court, arguing even conservative justices care about their legacy.
• "I think seven of them are in play for us. Three for sure, maybe the other four." — Anthony Romero on the possibility of swaying justices (13:14, 14:35)
• Discusses how public opinion, media, and history influence justices—comparing landmark cases like Korematsu as cautionary tales.

5. The Fight Against the “Unitary Executive”

• The "unitary executive" theory is critiqued as a threat to checks and balances, letting presidents act like kings:
  • "It's the idea that the executive branch...should be unitary, a step above the legislative and judicial branches." — Anthony Romero (15:35)
• This theory has emboldened Trump-era policies, leading ACLU to file "over 430 legal actions...over 100 with Trump 2.0 within the first hundred days" (17:01).

6. Legal Strategies: Volume and Delay

• Large amounts of litigation serve to dilute executive power, rob the government of momentum, and buy critical time for affected individuals.
  • "If you play for time, that can be a success...even if you know you're going to lose, playing for time is an effective strategy." — Anthony Romero (19:01)

7. High-Stakes Cases: Alien Enemies Act & Birthright Citizenship

• Alien Enemies Act:
  • Originally from 1798, used historically during declared wars to deport enemy aliens. The Trump administration invoked it against Venezuelan immigrants, despite no war.
  • "If we gave the German citizens due process during WWII, we have to give [Venezuelans] due process...I think we win this one hands down." — Anthony Romero (21:13)
• Birthright Citizenship:
  • Central to post-slavery America and the 14th Amendment. Trump’s attempts to end birthright citizenship are viewed as direct attacks on America’s core.
  • "This is the soul of America. It's how America fixed its original sin of chattel slavery." — Anthony Romero (24:44)
  • The ACLU prepped cases months in advance, mobilizing within two hours of Trump’s executive order (28:00).

8. Immigration Enforcement: "The Existential Thing"

• Ongoing expansion of federal deportation and detention infrastructure.
  • “$170 billion...to put the Department of Homeland Security on steroids, to build more prisons...We are just watching the beginning of this, ramping up on this attack on immigrants. And that's what I'm most worried about.” — Anthony Romero (29:13)

9. Supreme Court: Reading Justices, Dissents, and Briefs

• Lawyers pay close attention to dissenting opinions and oral argument dynamics to develop future legal strategies.

  • "Dissenting opinions...are critically important because they also give you nuggets about how to think about where to go forward. It's like a treasure hunt." — Anthony Romero (32:50)

• Insight:

  • The "game is to count to five" (majority of Supreme Court), and understanding each justice’s motivations is key (31:21).

10. Free Speech and Its Limits

• ACLU’s absolute defense of unpopular speech protects everyone by limiting government censorship powers.
  • "If you allow the government to censor the speech of someone you disagree with...they can come back and use that power against your own speech." — Anthony Romero (44:35)
  • Compares free speech precedents used to protect BLM with those established from defending Nazis, underscoring the universal application of rights.

11. Modern McCarthyism and Institutional Capitulation

• Romero warns of a new era where activists and immigrants are targeted for speech, likening it to McCarthyism.
  • Quoting the classic: "Have you no sense of decency, sir? At long last, have you left no sense of decency?" — Joseph Welch, cited by Romero (37:23)
• Disappointment in media and institutions quickly capitulating to executive pressure rather than upholding principle (39:08).

12. Civic Engagement and the “Firewall for Freedom”

• Romero encourages activism beyond voting or donating—local governments and officials play a vital role.
  • “If we can make those local jails off limits to the federal immigration officials, they're not going to be able to pick people up, they're not going to be able to deport them.” — Anthony Romero (48:05)
• Federalism is a strong check on the executive, and mobilizing local officials is crucial.

13. Personal Reflections: Leading as a Barrier-Breaker

• Romero reflects on being the first Latino and first gay head of the ACLU, and the Founders’ foresight:
  • “The genius of the founding fathers...is that they wrote in such a way that provided enough give in the joints so that people like me could step into roles and that the society...could envelope people that they didn't initially envision.” — Anthony Romero (51:25)
• He asserts hopefulness and a refusal to cede patriotism or optimism, arguing freedom is "about unleashing the great potential in every single person."

Notable Quotes and Memorable Moments

• On defending free speech:

  • "If you allow them to do this against people you don't like, they're gonna use that power on individuals you do like." — Anthony Romero (03:14)

• On being attacked from all political sides:

  • “I'm proud to eat takeout if necessary.” — Anthony Romero, on dining out after representing unpopular clients (09:28)

• On the Supreme Court’s motivation:

  • “They care, they care about what people think or say. They live in communities...” — Anthony Romero (14:35)

• On legal writing and advocacy:

  • “You got to give me a case for the history books...Amicus briefs, I need this to be a hit, baby.” — Anthony Romero (35:51, 35:59)

• On hope for the future:

  • "I refuse to cede the flag. I refuse to be pessimistic...this is really about unleashing the very best in each of us." — Anthony Romero (53:47)

Timestamps for Major Segments

• The ACLU’s Mission & GoFundMe Analogy: 03:53–05:19
• Nonpartisan Approach & NRA Case: 08:39–10:14
• Supreme Court Cynicism & Hope: 13:14–14:35
• Unitary Executive & Legal Overreach: 15:35–18:45
• Legal Strategy: Volume, Delay, and Defense: 19:01–21:54
• Alien Enemies Act Explained: 21:54–23:46
• Birthright Citizenship & ACLU’s Readiness: 24:44–28:00
• Fears for Immigration Enforcement: 29:13–31:00
• Supreme Court Dissent Analysis: 32:41–34:23
• Free Speech Defense & ‘Brandenburg v. Ohio’: 44:35–46:36
• Modern McCarthyism: 37:12–38:06
• Firewall for Freedom and Federalism: 47:54–49:58
• Romero’s Personal View on the Founders & Optimism: 51:25–53:47

Tone and Style

• Minhaj’s questioning is pointed but playful, frequently using humor to diffuse tension and make legal complexities accessible (“So it’s essentially a civil liberties legal GoFundMe?”).
• Romero is measured, principled, and direct but open about the emotional and strategic realities facing civil rights defenders.

Summary Takeaway

This episode is an incisive look at how civil liberties are protected and challenged in contemporary America. Whether discussing unpopular clients, the mechanics of Supreme Court persuasion, or how to mount a legal "shock and awe" against government overreach, Romero insists that principles must always trump partisanship. Amid criticisms of both political parties and a sobering analysis of current threats, he ends on a note of stubborn optimism—insisting that the American project’s greatest promise is to protect everyone’s right to self-actualization.