Bulwark Takes – “Even MEGYN KELLY Admits Trump's Chicago Threats Are Illegal!”

Podcast: Bulwark Takes
Date: September 7, 2025
Hosts: Sam Steinman (A), Tim Miller (B)
Main Theme:
This episode dives into recent comments from Donald Trump about sending troops into Chicago, analyzing the ominous social media messaging and legal boundaries, and featuring a notable moment: even conservative commentator Megyn Kelly admits Trump’s threats are illegal. Tim and Sam explore the significance of these statements and discuss the political and legal nuances, offering insight into the broader implications for U.S. democracy and law enforcement.

Key Discussion Points and Insights

1. Dissecting Trump’s Chicago “Deportation” Threats

• Trump’s social media post: “I love the smell of deportations in the morning. Chicago about to find out why it’s called the Department of War,” accompanied by an AI-generated ‘Apocalypse Now’-style image with helicopters and a burning Chicago skyline [00:00–00:53].
  • Tim: “I’m a little confused… I thought that they were talking about how the city was already on fire and that law and order was going to bring peace. I’m a little confused why in this AI image, Trump is kind of overseeing… a reign of fire on the city of Chicago.”
  • Sam agrees, noting the inconsistency in the imagery versus the rhetoric.

2. Megyn Kelly’s Legal Commentary

• Sam pivots to discuss Megyn Kelly’s recent show, in which she clearly states Trump cannot deploy federal troops to Chicago without state approval [01:21–02:53].
  • Megyn Kelly (clip): “He does not have the constitutional permission to do it. And I think, and I hope… I will [side with Governor Pritzker over Trump] if he does it because he can’t do it legally.” [02:53]
• Tim notes the significance:
  • Tim: “Megan, just calling balls and strikes. Love that from Megan… I think this signals real internal dissent and conversations about this [within the right].” [02:53]
• Discussion expands to whether Trump’s comments are mere “saber rattling” or preview attempts to test or push legal boundaries.

3. Trump’s Strategy: Wordplay, Signals, and Possible Moves

• Tim speculates Trump may be testing the waters, floating these ideas as trial balloons, and considers whether the next move is targeting blue cities in red states where the governor might cooperate [03:23–05:20]:
  • Tim: “Maybe the first step is to not go over the blue state governor’s heads, but go to blue cities and red states where you think the governor will welcome you and, you know, see how that goes… then maybe if something happens in Chicago… you can have a plausible excuse.”
• The hosts agree the legal pushback in previous attempts (e.g., L.A. riots, D.C.) has thus far limited federal overreach.

4. Legal Distinctions: ICE Operations vs. National Guard Deployments

• Sam raises the legal difference between ICE immigration raids and using the National Guard for crime suppression [05:20–06:49]:
  • ICE has different authorities than using military force for civilian law enforcement.
  • Reports Trump’s team is considering using a military base near Chicago as staging for an ICE operation, potentially circumventing the stricter legal constraints on National Guard deployments.

5. Blue State Governors’ Response

• Both discuss Illinois Governor Pritzker’s and Maryland Governor Wes Moore's messaging and pushback:
  • Tim: “I think Pritzker has been really strong… making it clear that it’s going to be a fight is an important first step here.” [06:49]
  • The hosts point out that while the threats are concerning, clear legal and political resistance exists.
  • There’s mention of more extreme counter-proposals from blue states, but consensus is that restraint and preparedness are effective for now.

6. The Power of Rhetoric, Memes, and Base Mobilization

• Analysis of Trump’s communication strategy that mixes literal threats and double meanings (dog-whistle effect) [08:31–09:40]:
  • Tim: “It’s that double meaning, he wants both. Some of his base want there to be a war on Chicago… and he wants the other members of his coalition to say, ‘Oh, the liberals are so crazy…’ It’s intentional.”
  • Both hosts stress the real-world consequences of such rhetoric, even if partially performative.

Notable Quotes & Memorable Moments

• Megyn Kelly (clip – Legal stance):
  “He does not have the constitutional permission to do it… I will if he does it [take Pritzker's side] because he can’t do it legally.” [02:53]

• Tim Miller (on GOP internal dissent):
  “I think this signals real internal dissent… I suspect she’s heard from people around Trump on this question.” [02:53]

• Sam Steinman (on justification language):
  “If you need a murder in Chicago as justification for going in, well, Chicago’s got those. Don’t worry, you have the justification.” [05:20]
  (Sardonic summary of how excuses for federal intervention might be manufactured)

• Tim Miller (on Trump’s approach):
  “With Trump, you always never really know, right. Is he just doing word diarrhea… or is he saying something because… he’s not a really good poker player. He’s kind of revealing where he’s going to go.” [02:53]

• Tim Miller (on the meaning of Trump’s meme):
  “It’s intentional. He wants that double meaning. And… it’s ominous. It’s not, not ominous.” [09:02–09:40]

Podcast Timeline & Timestamps

• [00:00–00:53] – Open: Trump’s message and Apocalypse Now meme dissected
• [01:01–02:53] – Megyn Kelly’s legal analysis, hosts’ reactions
• [02:53–05:20] – Tim unpacks Trump’s legal strategy, signals, and what GOP insiders might be hearing
• [05:20–06:49] – ICE vs. National Guard legality and speculation on operational approaches
• [06:49–08:31] – Evaluation of blue state governors’ responses and what’s working
• [08:31–09:40] – Importance of Trump’s rhetorical strategy and the danger of his "double meaning"
• [09:40–11:15] – Light banter, Tim’s history with Megyn Kelly and a peek into GOP media relations

Tone and Takeaways

• Candid, wry, and skeptical: Blunt, informed, and irreverent banter paired with clear-eyed analysis.
• Both Sam and Tim bring personal experience and a policy-savvy, narrative-driven feel, breaking down legal, political, and cultural stakes while maintaining their characteristic Bulwark edge.

Summary for New Listeners:
This episode is a sharp, accessible breakdown of Trump’s latest authoritarian-leaning rhetoric about Chicago, blended with astute legal and political commentary—made especially notable since even Megyn Kelly (a frequent Trump media booster) calls out the illegality of the proposal. If you want an informed, behind-the-lines take on why these debates matter and what they might signal for 2025 politics, Bulwark Takes provides just that.