The Weekly Show with Jon Stewart

Episode: A Conversation with Gov. JB Pritzker
Date: September 11, 2025
Theme: Responding to Federal Immigration Crackdowns and Threats to Democracy in “Operation Midway Blitz”
Guest: Illinois Governor JB Pritzker

Overview

In this episode, Jon Stewart sits down with Illinois Governor JB Pritzker to discuss Operation Midway Blitz—a massive federal immigration enforcement action targeting Chicago. The conversation delves into the current political climate’s implications for immigration, law enforcement, federal-state relations, rising authoritarianism, and the responsibilities of Democratic leaders. Stewart’s trademark wit frames a serious and urgent dialogue about threats to civil liberties, community safety, and democracy at large.

Key Discussion Points & Insights

1. Operation Midway Blitz: Federal Immigration Crackdown

• Context: The operation is a large federal initiative with ICE agents descending on Chicago, executing arrests with little coordination with local authorities. (03:12)
• Governor’s Perspective:
  • Less than ten arrests so far, but 300 agents are believed to be on the ground, led by Gregory Bovino, previously behind high-profile raids in LA. (03:12–04:29)
  • The intention, according to Pritzker, is to provoke unrest so the federal government can justify sending in the National Guard.
  • “Donald Trump wants to create a situation for Chicago where he can bring in the National Guard.” – Gov. Pritzker (04:05)

2. Legal & Constitutional Issues

• Posse Comitatus Act: Stewart raises the issue of using military forces for law enforcement, noting the Supreme Court recently ruled such use unlawful in LA; Pritzker explains how these rulings don’t automatically transfer to other jurisdictions. (04:29–05:09)
• Supreme Court Fallout: Supreme Court decision purportedly allows arrest based on skin color, accent, or language—Pritzker decries this as a dangerous precedent.
  • “Now… the Supreme Court ruled yesterday… it’s okay to arrest people just because of the color of their skin or because of an accent that they may have…” – Gov. Pritzker (05:09)

3. Chicago’s Resistance & Sanctuary Status

• Local Protections: Illinois has a consent decree making it harder for ICE to detain bystanders without cause. (07:16)
• Community Education: Ongoing education helps people know their rights—ICE cannot forcibly enter homes without a judicial warrant.
• Sanctuary City Clarification: Stewart and Pritzker clarify that sanctuary status does not bar cooperation with federal law on violent criminals but pushes back against administrative warrants. (13:01–13:06)
  • “We honor all judicial warrants… But an administrative warrant is just something an ICE agent can write themselves…” – Gov. Pritzker (12:38/13:06)

4. Differences Between Administrative and Judicial Warrants

• Administrative Warrants:
  • Issued by ICE agents without probable cause or judicial oversight; used broadly under Trump’s guidance.
  • “That whole paperwork thing that's called due process is habeas corpus, for goodness sake.” – Gov. Pritzker (14:33)
• Judicial Warrants:
  • Sought with evidence and due process—Chicago will cooperate in these cases.

5. Coordination (or Lack Thereof) with State Authorities

• Exclusion of Local Authorities:
  • ICE did not inform Illinois officials of their plans or operations, unlike previous administrations where coordination was at least attempted. (15:55–17:36)
  • Under Trump, ICE acts as a “rogue agency.” (17:00–17:36)
• Past vs. Present:
  • Biden-era operations more often involved notification and judicial warrants, Trump-era has returned to surprise actions and aggressive tactics.

6. Law & Order, Guns, and Political Narratives

• Chicago Stereotypes: Trump characterizes Chicago as uniquely dangerous, justifying extraordinary measures.
• Real Reasons for Crime:
  • Gun violence is exacerbated by lax gun laws in neighboring states, not by local policy failures.
  • “About 50% of all the gun crimes that are committed in Chicago are committed with guns that were purchased in another state.” – Gov. Pritzker (19:45)
• Weapons Policy: Illinois has banned assault weapons and adopted universal background checks, unlike surrounding states. (19:46–21:01)

7. National Guard and Militarization of Law Enforcement

• Risks of Deploying Out-of-State Troops:
  • “These folks are extremely well trained... They are not trained to do law enforcement.” – Gov. Pritzker (22:26)
• Request for Real Resources:
  • Pritzker calls for more ATF, FBI agents, not military deployments. (23:31)
  • “Please send us more ATF agents… Do NOT send military.” – Gov. Pritzker (23:31)

8. Federal Funding Cuts and Political Retaliation

• Cuts Harm Law Enforcement: Trump administration cuts ATF by 30% while claiming to fight crime. (26:40)
  • “Let’s debunk the myth that we have somehow defunded police. It’s Donald Trump that’s defunded police.” – Gov. Pritzker (27:25)
• Effective Violence Reduction: Illinois invests in community violence intervention and mental health programs—these are cut by federal government. (27:25–29:01)

9. Criminal Justice Reform: Ending Cash Bail

• Motivation & Results:
  • Illinois eliminated cash bail, letting judges detain based on danger, not means.
  • Results show no decrease in trial appearance rates since reform. (32:23–35:47)
• Accountability for Judges:
  • Ultimately, voters can remove judges making poor judgments, but recourse is limited. (34:03)

10. Root Causes: Poverty, Disinvestment, and Education

• Historic Disinvestment:
  • Focus on lack of state/federal support leading to entrenched inequalities in cities like Chicago. (36:09–37:47)
• Education as Crime Prevention:
  • Early childhood investments have proven effects on later life crime reduction. (37:47–38:28)
  • “Someone who goes to preschool is much less likely to end up in prison during the course of their life…” – Gov. Pritzker (37:49)

11. Democratic Governors, Collective Action, and the Limits of Power

• The Need for Unified Opposition:
  • Stewart presses Pritzker on why blue-state governors haven’t built a stronger, collective response to federal overreach. (43:09, 44:05)
  • Pritzker: “I believe…at the moment that Democratic governors should be standing up and speaking out, fighting forcefully, rhetorically…” (43:37/43:50)
• Coordination & Constraints:
  • Democratic governors and attorneys general share information and file lawsuits, but state-level levers against the federal government are limited. (45:27–47:21)
• Inspirations from History:
  • Pritzker invokes the example of Terry Sanford, arguing public officials must “be an upstander” in defense of democracy. (48:36–51:04)

12. Erosion of Democratic Norms

• Authoritarian Drift:
  • Worry about unchecked presidential power, Supreme Court’s abdication of its role, and GOP lack of independence. (52:01–53:31)
• Protecting Rights:
  • Pritzker’s administration is actively providing sanctuary protections for reproductive rights, within what state power allows. (54:04)
• COVID as Model for Collective Action:
  • Democratic governors coordinated in the pandemic and continue to consult, but large-scale unified action is hard.

Notable Quotes & Memorable Moments

• On Trump’s Chicago Operation:

  • “What they're trying to do is create a situation for Chicago where he can bring in the National Guard.” – Gov. JB Pritzker (04:05)

• On Administrative Warrants:

  • “An administrative warrant is what they are carrying around, looking for people. Now if they have somebody who's committed a crime, they can get a judicial warrant. That's not hard to get if you have evidence of it.” – Gov. JB Pritzker (14:03)
  • “That whole paperwork thing that's called due process is habeas corpus, for goodness sake.” – Gov. JB Pritzker (14:33)

• On Defunding Police:

  • “Let’s debunk the myth that we have somehow defunded police. It’s Donald Trump that’s defunded police.” – Gov. JB Pritzker (27:25)

• On Community Programs:

  • “We have peacekeepers that sit in the most violent communities on the corners and talk to those young people who are wanting to get involved in gangs… it’s worked… homicide rate has been cut in half.” – Gov. JB Pritzker (29:01)

• On Democratic Unity:

  • “I'm on Team Fight. I believe that we all ought to be standing up right now. This is about preserving our democracy.” – Gov. JB Pritzker (44:05)

• On Historical Perspective:

  • “What the survivors [of the Holocaust] taught me is…to ask yourself about what your values are…are you a collaborator? Are you a bystander…or are you an upstander? The survivors would tell you, be an upstander.” – Gov. JB Pritzker (48:36)

• On the Importance of Education:

  • “Someone who goes to preschool is much less likely to end up in prison during the course of their life… they've done longitudinal studies over 40 years to determine these things.” – Gov. JB Pritzker (37:49)

• Stewart’s Sarcasm and Resilience:

  • “If the Fourth Amendment means nothing, why does the Second Amendment mean something? I mean, they're picking and choosing...” – Jon Stewart (59:01)

Important Timestamps

• 03:12: Gov. Pritzker describes ICE operations and context of Operation Midway Blitz
• 04:29: The legal limits of using military for law enforcement
• 07:16: ICE’s disregard for local protocols and the value of community education
• 12:38–13:58: Detailed explanation of judicial vs. administrative warrants
• 19:45: Discussion of gun violence and “iron pipeline” from neighboring states
• 27:25: Pritzker on who is really defunding police and local programs
• 29:47: Broader discussion: crime, poverty, and community investment
• 32:23–35:47: Explanation of ending cash bail and results in Illinois
• 43:09: Stewart asks about collective action by Democratic governors
• 44:05: Pritzker on the need for unity and “Team Fight”
• 48:36: Holocaust museum lesson; upstander vs. bystander
• 59:01: Stewart’s Constitutional challenge: “If the Fourth Amendment means nothing...”

Tone and Final Thoughts

Stewart punctuates the urgent discussion with humor and skepticism, drawing out Pritzker’s passion and frustration regarding federal overreach and the erosion of democratic norms. Governor Pritzker is candid about both the limits and opportunities of state-level resistance, advocating for collective, outspoken Democratic action but acknowledging institutional constraints.

The episode closes with an affirmation of the need for local engagement, creative legal strategy, and—above all—moral clarity in the face of creeping authoritarianism.

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