Bulwark Takes — Conservative Podcaster BLASTS Trump’s Kimmel Crackdown!

Podcast: Bulwark Takes
Hosts: Sam Stein and Tim Miller
Date: September 18, 2025

Episode Overview

This episode examines the conservative and "free speech bro" podcast world’s reaction to former President Trump’s advocacy for a crackdown on Jimmy Kimmel and the fallout from Kimmel’s ouster. The hosts delve into how this incident has shifted the discourse on free speech, cancel culture, and government overreach, especially among right-leaning media figures who typically criticize liberal “cancel culture.” Notably, reactions from Barstool Sports, comedian podcasters, and others reveal cracks in conservative media’s support for Trump, with some calling out hypocrisy and expressing deep concern about government pressure on speech.

Key Discussion Points and Insights

1. Broad Reaction from Podcast/Comedy Right (00:00–02:14)

• Predictable yet Surprising: While it was expected that free speech advocates would dislike Trump’s crackdown on Kimmel, Sam and Tim are surprised at how many in the “bro” podcast world did not shy away from condemning it, despite traditionally being unsympathetic to Kimmel.
• Distinct Camps: These figures are culturally conservative, but not necessarily aligned with Kimmel, making their defense noteworthy.

“None of them really find him funny. Right. So for these guys, like, they could have just ignored this ... The fact that so many of them have spoken out, I think is pretty [noteworthy].” — Tim Miller (01:01)

2. Barstool Sports Response: Internal Division (02:14–07:31)

• Dave Portnoy’s Position (02:14–02:47):
  • Portnoy, Barstool’s founder, defended the network’s decision to oust Kimmel, trying to argue it wasn't cancel culture but legitimate consequences.
• Pushback from Barstool Personalities (02:47–04:53):
  • KFC Barstool: Provided a detailed critique, connecting FCC pressure to corporate mergers, and exposed it as being driven by money, not free speech.

    “It's always about the money. It's never about the free speech. It's never about protecting rights. It's always about the money and how to get it. I was dead wrong. Shit is fucked on so many levels.” — KFC Barstool (03:31)

  • Hosts note that this is a nuanced, sophisticated argument from a culture often stereotyped as vapid.
• Barstool Nate on Twitter (05:12–06:09):
  • Described the crackdown as “overreach and pretty insane,” wishing political affiliation wouldn’t obscure the reality.
  • Host comments on the “reverberation” of outrage across their feeds, with many recognizing this as direct pressure from Trump.

3. The Kirk Minahan Show: Brutal Takedown (06:45–07:56)

• Minahan, a conservative Barstool personality, offers the harshest rebuke, mocking the “extreme right” as hypersensitive and accusing Trump and Portnoy of opportunism.

“The extreme right are the biggest group of pussies that has ever existed in America ... because once in a while a fucking guy swam against girls, you fucking pussies have broken in half.” — Kirk Minahan (06:45)

• Hosts' Reflection: The language and attitude, taken from inside conservative podcast culture, is seen as potentially effective in calling out right-wing “snowflakery,” using their own tone to puncture MAGA grievances.

4. Comedians and Sports Podcasters Speak Out (10:24–12:27)

• Tim Dillon: Known for Trump-sympathetic jokes, posts that Kimmel’s ouster sets a bad precedent, and jabbed at both Trump and progressive censorship.
• Andrew Schulz: Issues a “both sides” post, less pointed but notable for the shift away from defending Trump.
• Akash Singh (Flagrant Podcast):
  • Expresses alarm, likening Trump’s move to government crackdowns on free speech in India, drawing a distinction between mob-based cancel culture and state-backed attacks.

    “Freedom of speech, I've seen it truly under attack in India ... This is closer to that than I think what the left was doing ... that's what makes it an actual attack on free speech to me.” — Akash Singh (11:57–12:27)

5. Underlying Motivations, Shifting Alliances, and Thin Skins (12:33–15:30)

• Changing Issues: Many in the right-leaning podcast/comedy space are animated by free speech, Covid restrictions, opposition to “woke” cancel culture, and a general anti-establishment stance—not traditional conservative policies.
• Trump Is Losing Them: These voices note that Trump is failing them issue by issue—on free speech, war, even their favored conspiracy theories.
• Audience Influence: Hosts highlight that these podcasters both shape and respond to their audiences, amplifying the significance of their criticisms of Trump.

6. Broader Implications: Chilling Effect, Media Silence & What It Means (15:30–20:24)

• Significance Beyond Podcast World: The hosts argue that podcast/comedy right’s condemnation signifies a real shift and reflects an emerging discomfort in Trump’s coalition.

• Chilling Effect in Corporate Media: While independent voices are outspoken, traditional corporate media (e.g., the Washington Post) have been slow, muted, or caveated in addressing the Kimmel ouster.

  “If you go to their editorial page, their actual editorial page ... there's nothing on Kimmel.” — Sam Stein (18:30)

• Local Media Concerns: Tim warns of further consolidation and right-wing, Fox-style control of local news as a looming threat.

  "We might be getting to a place where the local media is very foxish in huge swaths of the country, and that is bad." — Tim Miller (20:06)

• Silver Linings: Despite grim trends, the hosts see the open resistance from influential, right-leaning voices as positive, suggesting Trump’s attempts to intimidate or chill speech aren’t yet succeeding.

Notable Quotes & Timestamps

• Tim Miller (regarding Barstool criticism):
  “None of them really find him funny. Right. So ... the fact that so many of them have spoken out, I think is pretty [noteworthy].” (01:01)

• KFC Barstool:
  “It's always about the money. It's never about the free speech. ... I was dead wrong. Shit is fucked on so many levels.” (03:31)

• Kirk Minahan (about the MAGA right):
  “The extreme right are the biggest group of pussies that has ever existed in America.” (06:45)

• Akash Singh (Flagrant Podcast):
  “This is closer to [India] than I think what the left was doing ... that's what makes it an actual attack on free speech to me.” (11:57–12:27)

• Sam Stein (on mainstream media response):
  “If you go to their editorial page, their actual editorial page ... there's nothing on Kimmel.” (18:30)

• Tim Miller (on media consolidation):
  “We might be getting to a place where the local media is very foxish in huge swaths of the country, and that is bad.” (20:06)

Conclusion and Takeaways

• A significant segment of the right’s podcast and comedy world, often critics of “cancel culture,” are openly denouncing Trump’s effort to oust Jimmy Kimmel—a moment of rare cross-ideological consensus on free speech.
• The criticism is not tepid but forceful, with some using blunt, even profane language to call out hypocrisy and authoritarian overreach.
• The episode frames this as a meaningful, representative indicator of fraying support for Trump in cultural spheres crucial to his coalition.
• Simultaneously, the hosts highlight a worrying chilling effect within corporate and broadcast media, as well as potentially dangerous trends in local news consolidation.
• Despite concerns, the resistance of prominent cultural voices signals that, for now, America’s speech culture is “not cowed,” and there is room for optimism.

Listen if you want: A smart, unsparingly honest rundown of how culture-war podcasters are breaking with Trump over free speech—and why that matters more than it seems.