Podcast Summary

Podcast: Free Thinking Through the Fourth Turning with Sasha Stone

Episode: Barack Obama and the "Bitter Clingers"
Date: November 16, 2025
Host: Sasha Stone

Overview / Main Theme

Sasha Stone, a former Democrat who has re-evaluated her place on the political spectrum, delves into the deepening ideological and cultural rift in America, tracing today’s polarization back to Barack Obama’s 2008 “bitter clingers” comment. She contends this moment was a catalyst for the “virtual civil war” currently dividing the nation. Stone critiques leftist orthodoxy and media narratives, exploring how race, class, media power, Trump Derangement Syndrome, and the redefining of citizenship and American identity have fractured the country.

Key Discussion Points and Insights

1. Psychological Impact of Trump Derangement Syndrome

• Opening Reflection: Stone describes a landscape where friends and families are broken over political differences (00:21). She cites a viral tweet and features a psychotherapist diagnosing "Trump Derangement Syndrome" (TDS)—a pathological obsession and trauma response to Donald Trump.
  • Quote:
    Psychotherapist: “People are obsessed with Trump... They can’t sleep. They feel traumatized by Mr. Trump... This is a profound pathology. I’d even go so far as to call it the defining pathology of our time.” (01:15)
• Stone likens this to the South’s utopian vision prior to the Civil War, arguing the modern left is similarly gripped by mass psychosis when its worldview is threatened. (03:04)

2. The 2008 Fourth Turning: Bitter Clingers and the Birth of a New Divide

• Sasha Stone: Cites Neil Howe’s ‘Fourth Turning’ theory, arguing 2008 (Obama’s election, iPhone, bailout, and rise of social media) was the crisis that birthed twin populisms: Occupy on the left, Tea Party on the right (05:45).
• Obama’s “Bitter Clingers” Comment: Explored as a key moment where the left alienated large swathes of America.
  • Quote:
    Sasha Stone (citing NYT): “[Obama said] small town Pennsylvania voters, bitter over their economic circumstances, cling to guns or religion or antipathy to people who aren’t like them as a way to explain their frustrations.” (07:35)
• Political opponents framed this as “condescension” and evidence of elite detachment. (06:26)

3. Weaponization of Race and Media Narratives

• The Obama/Palin/Ayers controversy is revisited, showing how opponents used "guilt by association" and how the media started to polorize along racial lines (08:38–11:00).
• The Tea Party emerges and is quickly labeled racist by legacy media and organizations like the NAACP (11:45).
  • Quote:
    David Webb (Tea Party): “I think the NAACP... needs an enemy to maintain its power base.” (12:49)
• Narratives about race become the default tool to disqualify opposition, as opposition to Obama is routinely dismissed as racist (13:42–15:04).

4. The Rise of Identity Politics and Cultural Power-Shifts

• Critical race and gender theory entrench in academia and media as a reaction to alleged racism and classism on the right. Stone describes this as the “great feminization and the great awokening” (16:00).
• Hollywood and Big Tech are said to have consolidated cultural power for progressives. HBO’s "Game Change" (2012) is cited as a hit piece against Sarah Palin, cementing media narratives of Good vs. Bad Republicans (17:38–20:05).

5. The Flexibility and Power of Language in Shaping Reality

• Stone rues how the left's “superpower” is the manipulation of words and media: “‘Binders full of women’ becomes ‘good people on both sides,’ or ‘fight like hell’... The reality we shaped was everywhere.” (21:01)
• Accusations of racism and Islamophobia are characterized as potent “kryptonite” for silencing dissent (21:31).

6. The Changing Meaning of “American Identity”

• Stone draws a direct line from elite “utopia” thinking to the erasure of American commonality, replaced by globalist and identity-group alliances (32:14). Defending national citizenship or advocating for secure borders is reframed as racist.
  • Quote:
    Sasha Stone: “Your citizenship matters less than your white privilege. That is how illegal immigrants became the oppressed group...” (32:14)

7. Media, Monuments, and the Power of Symbolism

• Walter Kern and Matt Taibbi argue that even in poverty, people need things of beauty and shared meaning (34:37–35:16).
  • Quote:
    Walter Kern: “Trump is... speaking to a new kind of America in which a lot of people who don't feel particularly proud of anything at least will have a stake in a beautiful ballroom. That's a psychological technique of identification for people who feel powerless...” (35:18)

8. The New “Bitter Clingers”: Progressive Elites

• Stone turns Obama's phrase back on the left, calling Hillary Clinton, Barack Obama, and other progressive elites the new "bitter clingers" who cannot relinquish their utopian fantasy or their power (37:43).
  • Quote:
    Sasha Stone: “Now it's the left who are the bitter clingers. They can't accept defeat and they won't let go of the past of utopia.” (37:43)
• Stone concludes with a warning: the reality constructed by media elites is a false, divisive utopia that never existed and cannot last.

Notable Quotes and Memorable Moments (with Timestamps)

• On Mass Psychosis:
  “Trump's win in 2016 was a sign that half the country was not happy with how things were going and wanted change... the freeing of the slaves sent the south into mass psychosis... After 8 years of deeply-rooted propaganda... our country could not survive, sent those of us inside utopia cascading into madness.”
  Sasha Stone (03:04)

• On TDS as the Defining Pathology:
  “People are obsessed with Trump... This is a profound pathology. I’d even go so far as to call it the defining pathology of our time.”
  Psychotherapist on Fox News (01:43)

• On Obama’s “Bitter Clingers” Comment:
  “...small town Pennsylvania voters, bitter over their economic circumstances, cling to guns or religion or antipathy to people who aren't like them...”
  Sasha Stone quoting NYT/Obama (07:35)

• On Patronizing Racism:
  “The study found that when white liberals talk to black people, they... dumb down their vocabulary... white conservatives don’t do this... what could be more racist than the patronizing view that black people need to be protected from our big vocabularies?”
  Batya Unger Sargon (30:45)

• On Manipulating Reality:
  “Our superpower in the Obama years was manipulating the flexible nature of words to make them mean anything we wanted them to mean...”
  Sasha Stone (21:01)

• On the New “Bitter Clingers”:
  “Now it’s the left who are the bitter clingers. They can’t accept defeat and they won’t let go of the past of utopia.”
  Sasha Stone (37:43)

Important Segments with Timestamps

• [00:21] – Introduction to current climate and TDS
• [01:05] – Psychotherapist explains Trump Derangement Syndrome
• [03:04] – Stone draws analogy to Civil War and left’s utopian psychosis
• [05:45] – The “Fourth Turning” and 2008 as crisis point
• [07:35] – Obama’s “bitter clingers” and political aftermath
• [11:45] – Tea Party vs. NAACP and the emergence of media-weaponized accusations of racism
• [16:00] – The rise of cultural progressivism, “great awokening”
• [21:01] – Language manipulation as a tool of power
• [30:45] – Batya Unger Sargon on the patronizing racism of white liberals
• [32:14] – Citizenship, identity, and progressivism
• [34:37–35:18] – Walter Kern and Matt Taibbi on the power of communal symbols
• [37:43] – The left as today’s “bitter clingers” and concluding warnings

Tone and Style

Sasha Stone’s narrative is reflective, sometimes confessional, often pointed and critical of leftist orthodoxy. The tone alternates between personal reminiscence, polemic, and cultural criticism—mirroring the blog-essay style carried over from her Substack.

Conclusion

This episode examines how a fateful phrase from Barack Obama helped ignite the current American culture war and how control of language and narrative became the chief weapon of the ruling class. Sasha Stone contends the left, consumed by its own ideological certainty and media power, became the very “bitter clingers” it once derided. Through historic parallels, media case studies, and psychological analysis, the episode invites listeners to reconsider what it means to be American—and whether utopian dreaming is a dangerous substitute for reality.

For More

Visit sashastone.com for essays and future episodes.