Post Reports — "The National Guard arrives in Chicago"

Date: October 8, 2025
Host: Colby Ikowicz
Guest: Kim Bellware (National Reporter, The Washington Post)

Episode Overview

This episode delves into the recent escalation of federal immigration enforcement in Chicago under President Donald Trump, climaxing with the deployment of the National Guard to the city. Host Colby Ikowicz interviews Washington Post reporter Kim Bellware, who has been covering the developments from Chicago. The discussion covers the origins and realities of the crackdown, local reactions, high-profile incidents, legal challenges, and potential consequences for the city and nation.

Key Discussion Points and Insights

1. Intensified Immigration Enforcement and Political Context

• Chicago as a Political Symbol:
  • President Trump has made Chicago a focal point in his rhetoric about "Democratic cities" and crime.
  • "Chicago has always been a city that President Trump has fixated on... It's a shorthand for Democrats. It's a shorthand for liberalism. It's a shorthand for all of the things that are, you know, counter to what he supports in many ways." (Kim Bellware, 02:39)
• Operation "Midway Blitz":
  • The Trump administration launched "Operation Midway Blitz" in September, billing it as an effort to arrest undocumented immigrants with violent criminal records in Illinois.
  • In practice, arrests swept up long-time residents, workers, and even U.S. citizens, not just individuals with violent records.
  • "One of the most striking examples...immigration officials came and arrested a young family in front of their daughter." (Kim Bellware, 04:09)

2. Reality on the Ground vs. Federal Rhetoric

• Contrasting Narratives:
  • Federal authorities depict Chicago as descending into chaos, using "killing field" rhetoric.
  • Residents and reporters describe most neighborhoods as calm, with crime issues being serious but localized—not requiring military intervention.
  • "It's so incongruous with what we're hearing from the administration...with the reality on the ground." (Kim Bellware, 05:30)
• Effect on Community:
  • Residents, including children, witness traumatic raids and the disappearance of familiar community members like street vendors and service workers.
  • The police presence, raids, and reports of mistaken detentions have created widespread fear and confusion.

3. Notable Incidents and Media Coverage

• ICE Raids and Use of Force:
  • Raids have included militarized tactics, such as late-night assaults on apartment buildings with helicopter support.
    • "There was a Black Hawk helicopter hovering over the building. You have agents rappelling down, kicking in windows, arresting people..." (Kim Bellware, 07:50)
  • Local officials, like a city councilwoman, have been arrested for questioning ICE tactics.
• ICE Shooting Incident:
  • A woman was shot (at least five times) by a CBP agent in an altercation on the southwest side.
    • Differing accounts: DHS claimed the agents acted defensively after being boxed in; the woman's lawyer disputed key details.
    • The event triggered swift protests and amplified distrust.

4. Official Response and Legal Pushback

• State and City Leaders:

  • Governor J.B. Pritzker and Mayor Brandon Johnson have forcefully condemned the administration's tactics and rhetoric.
    • Pritzker: "Donald Trump is using our service members as political props and as pawns in his illegal effort to militarize our nation's cities." (Pritzker, 10:49)
  • Both leaders are united in litigation challenging the deployment of federal troops, arguing it's unconstitutional and unnecessary.
    • They filed for a temporary restraining order, but the judge postponed a decision.

• Federal Legal Grounds:

  • The President’s authority to "federalize" the National Guard is limited—typically requiring a state of insurrection or direct threat to federal property.
  • The Insurrection Act has only rarely been used (last in 1992 during the LA riots, at local request).

5. Grassroots Resistance and Community Mobilization

• Neighborhood Organization:

  • Residents are mobilizing through "know your rights" sessions, whistle-blower programs, phone/Signal trees, and social media.
  • Efforts are highly localized and personal—neighbors protect each other, especially the most vulnerable.
    • "These individuals who have been arrested by ICE...are absolutely the fabric of these neighborhoods." (Kim Bellware, 16:03)

• Whistle-Assembly Events:

  • Community events are distributing whistle kits to warn about ICE activity.
    • Imelda Milagro: "The purpose...is to be able to alert if they're nearby or if they're currently detaining somebody...That way, your neighbors could start showing out if somebody is being detained, and you could come out, take video of...the detention to make sure that their rights aren't being violated." (Milagro, 18:40/19:30)

Notable Quotes & Memorable Moments

• On Militarization and Political Motive:

  • Protester: "You don't ransack the building, break the windows...They're doing that because they want to create the pretext for bringing troops in, for making it seem like there is a war zone in Chicago. They're the ones creating that war zone." (Protester, 09:31)

• On the Real Impact of ICE Raids:

  • "These are the flower vendors. These are the ladies that make tamales. These are the guys who are, you know, working at grocery stores...when one of these people goes missing, there's that hole in the school community." (Kim Bellware, 16:03)

• On Legal Efforts:

  • "[Governor Pritzker's attorney] said the sovereign injury grows only more grave if the National Guard is allowed to be deployed in the city. He described this as really just government hostility towards a population and political leaders...that are at odds with the president." (Kim Bellware, 23:13)

Timestamps of Major Segments

• [00:02] — Introduction: National Guard arrives, ICE raids peak, protests erupt
• [02:39] — Bellware on Trump's narrative vs. Chicago's reality
• [03:41] — Launch of Operation Midway Blitz
• [04:09] — Real-life examples: Family arrests, community fear
• [05:30] — Contrasting administration rhetoric and local reality
• [07:50] — South Shore apartment raid
• [09:31] — Anti-militarization protester voices
• [10:15] — Pritzker and Johnson's pushback
• [11:02] — ICE-involved shooting described
• [15:44] — Grassroots resistance: Neighborhood organizing, whistle events
• [18:40/19:30] — Whistle assembly, Imelda Milagro's perspective
• [20:10] — State and city unity, legal challenge discussion
• [21:19] — Legal analysis on National Guard federalization
• [23:13] — Federal lawsuit development and judge's response
• [24:44] — Comparison to Portland, Insurrection Act explained
• [26:26] — LA riots precedent vs. today's federal deployments
• [26:54] — Fears for escalation and the future

Conclusion: Where Does Chicago Go Next?

With the National Guard present and ICE raids ongoing, many Chicagoans fear further confrontation and escalation instigated by federal forces could be used to justify even greater force, possibly under the Insurrection Act. At the same time, community solidarity and legal challenges continue to grow in defense of city residents.

"People are trying to keep a level head and are hoping that this dies down, is diffused somehow. But for the moment, it looks like it's only going to escalate in the short term."
— Kim Bellware (26:54)

Episode takeaway:
A fraught standoff between local democracy, federal power, and the lived reality of Chicagoans is unfolding—marked by deeply personal community resistance, heated legal battles, and an uncertain path forward. This episode offers nuanced, on-the-ground reporting that captures the crisis's complexity and its profound impact on the city's social fabric.