The Next Level - BONUS Secret: Why Are America’s Billionaires So PATHETIC?!

Episode date: October 14, 2025
Host: The Bulwark (JVL, Sarah Longwell, Tim Miller)
Episode starts: [00:30]

Episode Overview

In this energetic live episode, Jonathan V. Last (JVL), Sarah Longwell, and Tim Miller grapple with the baffling behavior of America’s billionaire class—particularly their recent political maneuvers and complicity in MAGA politics. The conversation quickly veers into a sprawling dissection of tech wealth, political cowardice, the shifting winds among elite donors, and the ongoing fallout from the Trump era in American politics. Laced with their trademark banter, sharp commentary, and memorable personal anecdotes, the podcast examines both current events and larger cultural and political trends, culminating in thought-provoking (and sometimes hilarious) exchanges about the state of American democracy, elite incentives, and what the future might hold.

Key Discussion Points & Insights

1. Why Are Billionaires So Pathetic? (Marc Benioff as Exhibit A):

• Tim Miller lambasts Salesforce CEO Marc Benioff, who has recently lamented San Francisco’s direction, called for the National Guard, and retreated to a life of luxury in Hawaii.

  • Quote: "Marc Benioff...has the big penis tower in San Francisco that he's created. He's made money. I mean, I guess this is capitalism ... He was a big donor to liberal causes...If there was a nonprofit group doing the stupidest progressive shit imaginable, Marc Benioff was funding them." ([02:33])
  • Quote: "He thinks San Francisco is a shithole now and he wants to send in the National Guard. ... These pieces of shit. Can you believe how cowardly these fucking people are?" ([04:21])

• Sarah Longwell points to peer pressure and shifting social norms among billionaire donors:

  • Quote: "It's actually social ... The billionaires moved ... as their peer group shifted ... we now have a billionaire class that is firmly in Trump's camp because ... they're too scared. ... It's a peer problem." ([05:57])

• Tim recalls a meeting with Keith Raboy (PayPal mafia) that soured him:

  • Quote: "This guy was like the fourth guy at PayPal ... this is why ... I still want somebody who supports capitalism. I know that trickle down economics works... My chef and my trainer, they get paid way more than the other chefs and the trainers in the marketplace." ([07:18])
  • Quote: "I walked out of there...I'm Bernie. I'm with Bernie now. This is it." ([08:23])

• Sarah on crony capitalism:

  • Quote: "What they are doing right now isn't capitalism. These same people who are preaching capitalism, they are putting the crony in crony capitalism." ([08:48])

2. Trump's Legal Persecutions and the Chilling Effect

• JVL wonders if Trump's legal attacks on enemies and critics (Comey, Tish James, John Bolton, Pam Bondi) could backfire or just further his narrative.
  • Quote: "Does the public go, oh, maybe that was fascism? Or does Trump just go, look, look at these rigged judges." ([11:02])
• Sarah: Downside risk to Trump is negligible; the chilling effect among elites and donors is very real.
  • Quote: "If you have... Pam Bondi comes out, and she's like, we cannot defend hate speech... She was doing that on behalf of Trump... But I think the downside risk is negligible." ([11:14])
  • Quote: "These people ... are maybe the first people we've seen really stand up... Every single one of them is saying, go fuck yourself, Donald Trump. ... I do think that emboldens people." ([12:14])
• Tim: Chilling effect is working; people are scared, and it's expensive.
  • Quote: "I think the chilling effect is so real and, like, the hassle is real. I mean, look at Jim Comey's life sucks right now." ([13:20])

3. Democratic Legal Strategy: Did Tish James and Alvin Bragg Overreach?

• Sarah argues cases against Trump in NY (Tish James, Alvin Bragg) were strategic mistakes, distracting from more substantive charges (Jan 6th, documents):
  • Quote: "I want to just give voice ... Both of those cases, I think were a huge mistake to bring, knowing what we know now." ([16:28])
  • Quote: "I can't make a folk hero out of her because ... she ran saying she was going to prosecute Donald Trump. She got elected doing that. And I just, I can't make a folk hero out of her because I think that that was an enormous mistake to run saying she was going to prosecute him..." ([17:43])
• Tim: The GOP's promise to let the "legal system work" was always a ruse—they never intended to convict or prosecute Trump legitimately.
  • Quote: "I think that many of...us would have made that deal... If Mitch McConnell and seven other Republican senators had voted to convict him and he never was gonna run again in exchange for not going to jail, I would have been happy..." ([18:29])
  • Quote: "There was never going to be an actual criminal case ... that he or any other Republican was ever going to admit was legitimate." ([20:19])

4. No Kings Protests and Right-Wing Fearmongering

• JVL raises the issue of the right labeling upcoming "no Kings" protests as antifa-driven and a "domestic terrorism" threat.
• Sarah: Exposes the right’s hypocrisy—chastising left-wing rhetoric while stoking threats against peaceful protesters.
  • Quote: "The idea that they have ... spent the last six weeks ... chastising people for their rhetoric ... to then turn around and put a target on ... people’s backs ... is bad." ([24:33])
• Tim: This won't work politically—no Kings crowd is “not scary” and is quintessentially American.
  • Quote: "That rhetoric worked in 2020... Like, that ain't fucking working here with this crowd. ... It's not a hate America rally." ([25:18])
• Sarah: The GOP is trying to foment civil conflict, but Americans haven't taken the bait.
  • Quote: "Their strategy is about turning Americans against each other ... actively...But I don’t think Americans want civil war at all." ([26:59])

5. Analysis of Governor Races: Safe Democrats or Missed Opportunities?

• JVL expresses concern about Mikie Sherrill’s race in New Jersey and general Democratic caution.
  • Quote: "She's running a real safe race ... I'm not ringing the alarm bells, but..." ([29:38])
• Tim critiques both Sherrill and Spanberger for running “bad...safe races” instead of seizing the narrative and capturing political energy.
  • Quote: "I think they've both run really bad races actually, like really bad, really safe races that are not up for the moment." ([31:15])
• Sarah: These are "stars," but now is the time to define the party more boldly.
  • Quote: "This is the time ... you get a chance to define what the Democratic Party is at a time where it desperately needs definition." ([33:30])
• Debate over Winsome Sears (VA): Her extremist views (e.g., okay to fire someone for being gay) are a liability, but the Democratic response needs more courage and directness.
  • Quote: "Winsome Sears wasn't saying...that's not true. She was saying, that's not discrimination." ([35:31])

6. Swing Voters and Complicated Political Calculus

• JVL & Sarah discuss findings from recent focus groups:
  • Swing voters are frustrated with Trump for different reasons, but their concerns vary—some dislike his economic policy, others are upset about culture-war issues, and some are simply “balancing columns” of pros and cons.
  • Quote (Sarah): "The most interesting thing ... was the way in which voters ... take some things from column A...'I don't like these things.' What we don't do, though, that these voters do is say, but there's a handful of things I do like that he's doing, and I'm gonna balance these two things out." ([43:06])
• Key insight: Some will trade substantive economic pain for culture-war victories, e.g., “I’m so angry about prices ... but I’m glad you can’t transition ... anymore.” ([44:07])
• Quote (JVL): "I'll take fascism so trans kids can't play soccer. And I think that's a super weird trade." ([44:07])

7. The Perverse Appeal of 'Sincere' MAGA: Marjorie Taylor Greene and Others

• JVL raises the idea that some figures like Marjorie Taylor Greene (MTG) are at least authentic—can that be useful or less dangerous?
• Tim (unexpectedly) agrees MTG’s populist wedge, especially on economic resentment, is the correct break point to fracture MAGA.
  • Quote: "Only one [House Republican]...looked in the mirror and said, I don't think I can sleep well at night... and that somehow is Marjorie Taylor Greene." ([48:17])
• Sarah strongly disagrees MTG is acting morally—she sees her positioning as calculated, aiming for post-Trump relevance.
  • Quote: "Marjorie Taylor Greene understands the MAGA base...better than Trump does ... She sees a political future for herself in a post-Trump world." ([51:05])

Notable Quotes & Memorable Moments

• Tim Miller, on Billionaires:
  “These pieces of shit. Can you believe how cowardly these fucking people are?” ([04:21])
• Sarah Longwell, on Social Incentives:
  “The billionaire class that is firmly in Trump's camp...it's a peer problem.” ([05:57])
• Tim, after a tech billionaire meeting:
  “I'm Bernie. I'm with Bernie now. This is it.” ([08:23])
• Sarah, on Tish James and Bragg:
  “I can’t make a folk hero out of her because...she ran saying she was going to prosecute Donald Trump.” ([17:43])
• JVL, mockingly:
  “I would take Marjorie Taylor Greene over JD Vance every damn day.” ([52:27])
• Sarah, shutting it down:
  “She sees a political future for herself in a post Trump world...and that is going to have some juice. And I'll tell you the scariest thing about it is that it is going to make the Marco Rubio JD Vance ticket look positively normal by comparison.” ([51:05])
• On swing voters (Sarah):
  “I'm so angry about prices. ... But I'm glad you can't transition ... anymore. ... Is that, like, does it matter to you so much what somebody else does with their body that, like, you're gonna continue to just be that poor?” ([44:07])

Important Timestamps

• Marc Benioff rant – ([02:20]–[05:13])
• Billionaire social incentives – ([05:57])
• Keith Raboy/PayPal mafia anecdote – ([07:18])
• Crony capitalism breakdown – ([08:48])
• Trump’s legal strategy/chilling effect – ([09:49]–[15:31])
• Dems’ indictment strategy critique – ([16:28]–[21:06])
• No Kings protest, right-wing backlash – ([23:20]–[26:59])
• Mikie Sherrill/Abigail Spanberger critique – ([29:38]–[34:26])
• Winsome Sears debate – ([35:11]–[36:53])
• Swing voter discussion – ([39:22]–[45:08])
• Marjorie Taylor Greene authenticity debate – ([45:49]–[53:35])

Tone and Style

• Language: Candid, occasionally profane, direct.
• Tone: Sardonic, skeptical, self-aware, irreverent, but alternates between genuine frustration and hope.
• Speaker attribution: Clear, with playful ribbing and fast-paced banter, especially between Tim and Sarah.

Conclusion

This episode is a tour de force of Bulwark-style political commentary: equal parts condemnation of billionaire cowardice, darkly funny confessional about the frustrations of modern political activism, and sharp, sometimes despairing insight into both elite and voter psychology. The hosts’ exasperation over the complicity and herd mentality of the ultra-wealthy is matched only by their frustration with Democratic caution and the persistent, puzzling resilience of Trumpism—but they never lose sight of the baffling, human idiosyncrasies that shape American politics.

[Want the rest of the show? Join Bulwark Plus, says JBL at the end.]