Bulwark Takes: Tim GRILLS Daily Caller Editor (w/ Dylan Houseman)

Date: September 25, 2025
Host: Tim Miller (The Bulwark)
Guest: Dylan Housman (Editor-in-Chief, Daily Caller)

Episode Overview

In this episode, Tim Miller invites Dylan Housman of the Daily Caller for a frank cross-ideological discussion, responding to The Bulwark’s recent critiques of a Trump interview published by Housman’s newsroom. The conversation winds through media bias, the challenges of political interviews, Trump administration controversies (from border policy to foreign affairs to corruption), and broader debates about free speech, immigration, and even USAID. The tone is pointed but open, with both participants pressing hard on each other’s assumptions.

Key Discussion Points & Insights

1. Setting the Stage: Mocked Interview and Cross-Ideological Dialogue

• Tim explains the origin of the episode: a Bulwark video critiqued a Daily Caller-Trump interview for being “absurd,” and Housman felt the criticism was unfair ([00:52]).
• Dylan defines the Daily Caller as a “conservative right-wing, fact-based news publication” and outlines its history, noting Tucker Carlson’s past involvement ([01:46]).

2. Media Dynamics & Trump Interviews

• On Interviewing Trump:
  • Housman insists it’s tricky to get substantive answers from Trump without first making him comfortable, defending lighter, attention-getting moments chosen for the Daily Caller feature ([04:07]):

    “If you want to make news, if you want to get interesting things out of [Trump], you have to get him comfortable and have him in a place where he's not going to be overly defensive.” ([04:07] — Dylan Housman)

• Tim argues some questions were “a little bit of a suck up—about Mount Rushmore and media bias”—and wonders if the coverage glossed over more serious issues ([03:56], [05:16]).

3. Trans Shooter Narrative & Mass Shooting Statistics

• Contention over framing:
  • Tim challenges Daily Caller’s framing connecting mass shootings to “gender ideology,” questioning the accuracy and potential to stoke animus toward trans people:

    “Obviously half the mass shootings in this country aren't from trans folks. And if you're going to look at a more common trend about mass shooters, like, they're mostly 20 year old white dudes.” ([07:45] — Tim Miller)

  • Dylan counterargues definitions of “mass shooting” are flexible and views trans identity as “an ideological, social contagion.”

    “If you view it as this ideological, you know, social contagion of sorts... then it doesn't really make sense to lump it in as a demographic category, like someone's skin color.” ([08:21] — Dylan Housman)

• Tim asserts the comparison isn’t neutral and would be provocative if applied to, say, Christians instead:

  “You guys would be mad at me if I had an interview with a prominent Democratic official and said, you know, half the shooters have been Christian. Maybe Christian ideology is running them down...” ([08:55])

4. Trump Administration Performance: Foreign Policy, Corruption, Immigration

• Foreign Policy – Ukraine & Gaza:
  • Dylan credits Trump with having “an end state in mind” for conflicts, regardless of changing tactics ([11:39], [14:49]).

    “I think he has an end state in mind. He wants the war to end.” ([11:39] — Dylan Housman)

  • Tim calls out inconsistency and failed strategy:

    “His entire stated policy was a complete failure ... now they just switched sides to go to essentially the Biden position yesterday. How is that not a demerit?” ([12:10] — Tim Miller)

• Border Policy:
  • Dylan touts success in securing the border via executive action, claiming it addressed a “kitchen table issue” for voters ([26:20]).

    “Trump came into office and it basically instantly stopped just based on executive actions of what he was doing in his rhetoric alone...” ([26:20] — Dylan Housman)

  • Tim pushes back against negative migration:

    “I don't think you want to live in a country that has net negative migration. I think it's against the American tradition.” ([27:53] — Tim Miller)

• Controversial Deportations:
  • Tim presses Housman on Trump’s policy of sending suspected gang members (including possible innocents) to foreign prisons in El Salvador ([16:40]-[21:14]) and likens it to a violation of due process.

    “We never sent people to a foreign prison camp before this time.” ([18:05] — Tim Miller)

  • Dylan concedes some may have been wrongly deported but maintains this isn’t uniquely atrocious compared to past issues in law enforcement ([19:05], [20:20], [20:39]).
• Corruption and Cryptocurrency Controversies:
  • Both agree the Trump administration shouldn’t be selling stablecoin to foreign (esp. Chinese/UAE) interests ([25:10]):

    “I don't think it's a good look to be selling crypto to foreign investors and, and have foreign countries involved...” ([25:46] — Dylan Housman)

  • On bribery scandals (e.g., Tom Homan), Housman is unhappy with shutting down investigations if credible evidence exists ([24:18]).

    “If one of my reporters took 50 grand to write a story in a kava bag. No, I would not keep them.” ([24:30] — Dylan Housman)

5. Free Speech, Crackdowns, and Campus Rhetoric

• Disagreement over Vice President's Call to Report “Wrong Talk”:
  • Tim flags concern about the Vice President encouraging people to report neighbors and colleagues for “wrong talk” ([28:15]).
  • Dylan:

    “If you publicly celebrate the execution of someone for their political statements, I'm very comfortable with you losing your job.” ([28:36] — Dylan Housman)

  • Both concede discomfort with overreach, especially in prosecutions and mob-piling over Israeli or Palestinian discourse ([30:17]).

    “The Israel stuff is, I think, different. I do not think we should be deporting people just because they write an op ed about Israel being bad. I think that's... silly.” ([30:17] — Dylan Housman)

6. Foreign Aid and USAID Discussion

• Policy Tension between Soft Power and Scrutiny:
  • Tim wonders if Housman’s Christianity inspires second thoughts about cutting aid to vulnerable populations, contrasting limited USAID costs with other policies ([32:25]-[33:09]).
  • Dylan clarifies:

    “I think we should be funding things like PEPFAR and programs that help vulnerable people and protect them... What I think is bad is using USAID to try to destabilize foreign governments or spread wacky left wing ideology around the world, which doesn't really serve anybody's interest.” ([34:03] — Dylan Housman)

  • The two end on common ground: opposition to “starving children.”

Notable Quotes & Memorable Moments

• On Media Framing:

  “A little bit of suck. I mean, we start with media bias. We talk about whether we're going to name things after him. It's going to be on Mount Rushmore.”
  — Tim Miller ([03:56])

• On Trump’s Ukraine Policy:

  “He tried to butter up Putin, and now he's switching because it didn't work. So I don't think that's a demerit...”
  — Dylan Housman ([11:39])

• On Reported Corruption:

  “If one of my reporters took 50 grand to write a story in a kava bag. No, I would not keep them.”
  — Dylan Housman ([24:30])

• On Crypto Ethics:

  “I don't think it's a good look to be selling crypto to foreign investors and, and have foreign countries involved... No, it's not a good look.”
  — Dylan Housman ([25:46])

• On Border Security:

  “We had an entire discourse for weeks about how we needed to pass new laws ... and Trump came into office and it basically instantly stopped just based on executive actions ...”
  — Dylan Housman ([26:20])

• On USAID & Christian Values:

  “You know, I'm against starving children. I don't think that's a crazy take. I think Marco Rubio is as well.”
  — Dylan Housman ([34:27])

Timestamps for Important Segments

• [00:52] — Tim introduces Dylan and sets up the episode’s cross-ideological aim.
• [03:54] — Tim critiques the tone of the Trump interview.
• [06:40] — Debate over mass shooting statistics and trans shooter narratives.
• [10:29] — Dylan offers his broad assessment of Trump’s presidency.
• [11:05]-[12:57] — In-depth back-and-forth on Ukraine strategy under Trump.
• [16:40]-[20:39] — Dispute over the ethics and process of deportations to foreign prisons.
• [23:26]-[25:58] — Corruption, Epstein files, and criticisms over selling crypto to foreign interests.
• [28:15]-[31:30] — Controversy over crackdowns on speech about Israel, Charlie Kirk, and campus activism.
• [32:25]-[34:03] — The ethics and politics of foreign aid, USAID, and American values.
• [34:38] — Episode closes amicably, with Tim thanking Dylan for engaging across lines.

Concluding Tone

This episode reveals sharp ideological divides but doesn’t devolve into personal attacks. Both Miller and Housman stand by their political commitments, probe for logical consistency in each other’s views, and close on a note of grudging common ground, especially on the humanitarian front.

For listeners craving nuanced debate across the partisan divide—especially around media coverage, policy ethics, and the fraught language of today’s political culture—this fast-paced, sparring episode delivers clarity, disagreement, and occasional consensus.