The Briefing with Jen Psaki

Episode: Pritzker readies residents for a CHICAGO SHOWDOWN as Trump amasses troops
Date: September 6, 2025
Host: Jen Psaki (MSNBC)
Main Guests: Illinois Governor J.B. Pritzker, Congressman Jamie Raskin, Iowa State Representative Josh Turek

Episode Overview

This episode centers on the looming standoff in Chicago as former President Trump prepares for a possible federal deployment—mirroring controversial actions previously seen in Los Angeles. Jen Psaki interviews Illinois Governor J.B. Pritzker, delving into his response and preparations amid a lack of communication from the federal government. The show also covers new developments in the investigation into the Epstein files and finishes with a discussion on the 2026 Senate race in Iowa and the economic impacts of Trump’s recent policies.

Key Discussion Points & Insights

1. Federal Deployment Threats in Chicago

Host Commentary (01:00–04:55)

• Trump is preparing to send federal immigration agents and possibly the National Guard into Chicago, under the pretext of fighting crime.
  • Despite dropping crime rates in Chicago for four years (violent crime has dropped for a decade), Trump called Chicago a "hellhole" and stated:

    “We're going in. I didn’t say when, but we're going in.” (01:55)

• Parallels drawn between this and Trump’s recent Los Angeles deployment, which reportedly cost taxpayers $120 million and likely violated civil rights.
• The Pentagon has approved use of the Great Lakes Naval Station, 35 miles north of Chicago, as a hub for immigration operations.
• Hundreds of federal immigration agents and unmarked vehicles are reportedly en route; local authorities have limited info about the federal government’s precise plans.
• Security fences are being erected in downtown Chicago, particularly around the Federal Plaza—considered the likely epicenter of both the operations and ensuing protests.
• Governor Pritzker’s strategy includes proactive communication with residents to avoid panic and resist the “cynical effort” to normalize military presence.

2. Interview: Governor J.B. Pritzker on Defending Chicago

(04:55–23:19)

Lack of Federal Communication

• Pritzker confirms there has been almost no communication between the White House and state officials.

  "No. Which is shocking, really. The federal government not communicating with state government about what is supposed to be a law enforcement action by themselves. That's unheard of, really." (05:20 – Governor J.B. Pritzker)

• Only received a belated call from Gregory Bovino (CBP and ICE leader involved in LA) to state they’d be “in place by the end of this week” with no details on the number of agents, scope, or neighborhoods affected. (06:11)

Scale & Rumored Scope

• Pritzker relies on second- and third-hand reports (often from concerned federal/military employees) indicating:
  • Estimated 300 agents to be stationed at Great Lakes, possibly targeting communities like Little Village and Pilsen as early as the next morning. (08:26)

Repetition of LA "Playbook"

• Psaki and Pritzker see a repeat of LA’s tactics: a federal ICE operation intended to incite protest, then claim that unrest justifies greater federal and military presence.

  “It's, I believe, a nefarious plan… one that's been repeated over and over again by tyrannical dictatorships across history…” (09:59 – Governor J.B. Pritzker)

• Pritzker vows to fight any illegal deployment, warning of the possible constitutional crisis if courts don’t enforce restrictions like Posse Comitatus.
• Emphasizes that federal troops are "trained for war", not "crowd control or fighting crime," and suggests if Trump wishes to help with crime, he should send more ATF/FBI/DEA civilian law enforcement—not the military. (12:24)

Public Response and Legal Tools

• Residents are urged to film federal actions and ICE activity to document any potential legal violations.

  "Pull out their iPhone or their Android phone and film what they're seeing… so we can know if, in fact, laws are being broken by these federal officials..." (13:59 – Governor J.B. Pritzker)

• Administrative warrants do not allow forced entry; only judicial warrants (rare in these scenarios) would suffice.

National Guard Concerns & Elections

• Once federalized, National Guard troops' legal role is extremely limited to the protection of federal property, unless there's an insurrection or attack.

  "What it has to do with is he's trying to set the stage for interference in the elections in 2026 and in 2028." (16:26 – Governor J.B. Pritzker)

• Pritzker suspects the ultimate objective is election interference, citing requests for voter data and mid-decade redistricting pushes.

Court Battles and Blue State Targeting

• Legal action is planned but effectiveness is uncertain until Illinois courts rule, even if precedents are set in California.
• Trump’s deployments notably target blue states/cities despite Republican-led areas experiencing higher crime rates.

  "You don't see any activity in a Republican state or Republican city. And yet when he says it's all about crime, those Republican states have higher crime rates... So, you know, this isn't about that." (22:04 – Governor J.B. Pritzker)

3. Epstein Files and DOJ Cover-Up

Guest: Congressman Jamie Raskin (27:27–31:24)

• Congressional Republicans’ resistance stalls the release of the full Epstein files; DOJ has released only about 1% of the documents.
• Raskin previews an upcoming Democratic report documenting how the Trump administration has gutted anti-human trafficking and anti-domestic violence efforts.

  "This is now becoming clear a whole system that the Trump administration is committed to." (28:12 – Congressman Jamie Raskin)

• Strong criticism of Speaker Mike Johnson’s attempt to paint the Epstein investigation as a "hoax".

  "A hoax is a corruption scandal or a crime that Donald Trump doesn’t want anybody talking about anymore. It couldn’t be any clearer." (30:11 – Congressman Jamie Raskin)

• Victims are actively advocating, and there is bipartisan support for full transparency despite attempts at stonewalling.

4. Economic Policy Rollbacks & Consequences Under Trump

Host Commentary (33:25–37:51)

• Trump administration has repealed multiple consumer protection rules enacted under Biden—airline compensation, overdraft fee caps, and the Click to Cancel rule for subscriptions.
• Host lampoons Trump’s out-of-touch attitude with the infamous "$2 plane ticket" remark:

  "Take an airplane, it costs you $2. It costs you nothing." (33:48 – Trump, quoting)

• August jobs report: only 22,000 new jobs, unemployment up to 4.3%, June numbers revised downward (first net job losses since peak pandemic).
• Trump fired the head of the Bureau of Labor Statistics after last month's poor report.
• Economic prospects "will be better in a year or two, maybe even two," according to Trump, walking back earlier promises of immediate recovery.

  "The real numbers that I'm talking about... will be in a year from now. And our big year won’t be really next year. I think it’ll be the year after." (37:39 – Trump)

5. Iowa Senate Race Spotlight: Josh Turek

Guest: Iowa State Rep. Josh Turek (39:56–44:34)

• Turek distinguishes himself through his athletic and advocacy background, flipping a deep-Trump county in his own state race by six points.
• Asserts that Iowa remains a "common sense state" with a history of electing Democrats, despite recent GOP victories.

  "At our essence, Iowa, we are a common sense state... and we've got an amazing opportunity for Iowa to be the center of the political universe in 2026." (41:14)

• Central campaign issues: lowering costs, health care, wage growth, pharmaceutical costs, water quality, “kitchen table” matters.
• Describes his personal experience with economic hardship and extensive medical issues as core to his credibility.
• Denies Washington meddling in his candidacy after a rival's early endorsement:

  "Absolutely not. J.D. and myself, we are very close friends. This was about friendship. It's sad that people are that cynical." (43:48 – Josh Turek)

Notable Quotes & Memorable Moments

• "We're going in. I didn't say when, but we're going in." (01:55 – Donald Trump, quoted by Jen Psaki)
• "I've never seen anything like this... It's kind of a frightening development in the history of the country..." (05:20 – Gov. J.B. Pritzker)
• "We're ready to go to court when they kind of trip the wire, so to speak... If the courts don't rule... we're then at the whims of a fighting force that they're planning to send here." (09:59 – Gov. J.B. Pritzker)
• "Pull out their iPhone... and film what they're seeing. Take a video of everything that you see so that we can know if, in fact, laws are being broken..." (13:59 – Gov. J.B. Pritzker)
• "What it has to do with is he's trying to set the stage for interference in the elections in 2026 and in 2028." (16:26 – Gov. J.B. Pritzker)
• "This is now becoming clear: a whole system that the Trump administration is committed to." (28:12 – Congressman Jamie Raskin)
• "A hoax is a corruption scandal or a crime that Donald Trump doesn’t want anybody talking about anymore." (30:11 – Congressman Jamie Raskin)
• “Take an airplane, it costs you $2. It costs you nothing.” (33:48 – Donald Trump)

Timestamps for Key Segments

• Federal Deployment Threat in Chicago – 01:00–04:55
• Interview: Gov. J.B. Pritzker – 04:55–23:19
  • Lack of communication – 05:01–06:30
  • Potential scale and agents – 08:26–09:30
  • Legal response/playbook – 09:59–13:01
  • Public documentation strategy – 13:59–15:55
  • National Guard and elections – 16:26–18:23
• Epstein Files (Rep. Jamie Raskin) – 27:27–31:24
• Economic Rollbacks Under Trump – 33:25–37:51
• Iowa Senate Race: Josh Turek – 39:56–44:34

Episode Tone & Style

The episode maintains Jen Psaki’s signature sharp, informed, and occasionally sardonic tone, with a clear, urgent warning regarding the Trump administration’s maneuvers in Chicago and elsewhere. Guest segments maintain a serious and direct approach, focused on constitutional, legal, and electoral issues, as well as stories of resilience and advocacy.

For listeners seeking clarity on current government actions, strategies for resisting federal overreach, and the state of key midwestern political races, this episode provides crucial, up-to-date insight.