Sarah Longwell: Trump’s Failures Give Democrats a Once-in-a-Generation Opening | Bulwark on Sunday

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Kristol, W. (2026, September 6). Sarah Longwell: Trump’s Failures Give Democrats a Once-in-a-Generation Opening | Bulwark on Sunday. The Bulwark. https://www.thebulwark.com/p/revealing-the-bulwarks-secret-origin

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Quick Summary

Sarah Longwell argues in her new book that the failures of Donald Trump's presidency provide Democrats with a rare opportunity to make significant gains. Longwell, who has conducted extensive voter focus groups, believes that Democrats can learn from Republican political infrastructure and create a broad pro-democracy coalition to take down Trumpism. The key to success, according to Longwell, is finding ways to manage internal disagreements within this coalition. In her book, "How to Eat an Elephant: One Voter at a Time", Longwell draws on years of research to outline a strategy for defeating Trumpism.

Written locally by qwen2.5:14b on 2026-09-07, using this article's own text rather than the other coverage of the same event (that is the story summary below).

AI analysis runs on qwen2.5:14b, locally

Story summary

Sarah Longwell, author of the book How to Eat an Elephant: One Voter at a Time, believes that Donald Trump's failures have created a rare opportunity for Democrats to make significant gains in the upcoming elections. According to her, this is a "once-in-a-generation opening" for Democrats, who can learn from Republican political infrastructure and use it to their advantage. Longwell argues that the changing media environment has shifted the balance of power in favor of Democrats, allowing them to capitalize on Trump's weaknesses. She suggests that a broad pro-democracy coalition can be formed to manage internal disagreements and develop a successful strategy against Trumpism.

Written for “Trump's Election Impact Assessed” on 2026-10-22, grounded in this article and the 0 other(s) covering the same event.

Story

📰 Trump's Election Impact Assessed

Politics · 1 article(s) covering the same event.

Compared with similar articles

This article reads centre and hedges 25% of its claims. Each row says how that neighbour differs.

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Noahpinion

⚖️ Leans strongly left further left than this 🔴 6% hedged 5 of 78

“Article A is an opinion piece about Donald Trump's failures, while Article B is an interview with Sarah Longwell about her book on opposing Trump, which does not describe the same specific happening”

Legal veterans lead fightback against Trump’s ‘full-out assault on democracy’ different event · 90%

The Guardian

⚖️ leaning not scored 🔴 18% hedged 11 of 60 📰 publisher trust 69

“Article A mentions Trump's failures in general, while Article B specifically refers to 'Trump’s authoritarian executive orders on voting and other presidential actions'”

The Stakes of America’s 2026 Midterm Elections different event · 80%

TIME

⚖️ Leans left further left than this 🔴 15% hedged 5 of 34 📰 publisher trust 59

“The articles discuss unrelated topics: one about the state of democracy in the US and the other about a book discussion on opposing Trump”

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Toronto Star

⚖️ Leans left further left than this 🔴 19% hedged 10 of 53 📰 publisher trust 63

“Article A appears to be a general reflection on the 2024 election cycle, while Article B discusses a specific book by Sarah Longwell and its discussion of Trump's failures”

Democrats hoping to appear ‘normal’ as they roll out their blue wave of weirdos ahead of critical midterms different event · 80%

New York Post

⚖️ Leans strongly right further right than this 🔴 6% hedged 2 of 36 📰 publisher trust 66

“Article A discusses a book discussion about Trump's failures giving Democrats an opportunity, while Article B is a general commentary on the upcoming midterm elections and the choice between Trump's administration and the Democratic party.”

Adam Jentleson and Pablo Torre: This Country Is Being Scammed different event · 80%

The Bulwark

⚖️ Leans strongly left further left than this 🔴 7% hedged 1 of 15

“Article A discusses Sarah Longwell's views on Trump's failures and a potential opportunity for Democrats, while Article B mentions Adam Jentleson and Pablo Torre discussing corruption and the rich getting rewarded in the US, without any apparent connection to Longwell or the topic of Trump's failures”

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Washington Examiner

⚖️ leaning not scored 🔴 10% hedged 3 of 29 📰 publisher trust 66

“Article A discusses a book about opposing Trump and does not mention an election or convention, while Article B talks about a Republican midterm convention putting Trump on the ballot”

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Uncertain

25%

1 of 4 hedged ("reportedly", "may", "according to")

Leaning

Centre

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Publisher

The Bulwark · 479 article(s) · 0 correction(s) detected

No corrections detected for this publisher. That may mean careful reporting, or simply that nothing has been checked.

Who wrote this

William Kristol

21 article(s) here · 1 carrying a prediction

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2026-10-07 · assertive framing · Reasons for Hope. Reasons for Alarm.

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2026-10-06 · assertive framing · Grandpa Trump Is Getting Desperate

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2026-10-01 · assertive framing · Trump + AI = Blue Tsunami

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Also by William Kristol

James Carville’s Midterm Predictions | Bulwark on Sunday

2026-10-18 · The Bulwark

Hegseth Wants You to Watch a Snuff Film

2026-10-09 · The Bulwark

Reasons for Hope. Reasons for Alarm.

2026-10-07 · The Bulwark

Grandpa Trump Is Getting Desperate

2026-10-06 · The Bulwark

Nothing else under this byline is closely related to this article, so these are simply their most recent.

All 21 articles by William Kristol →

Narrative

Claims (4 extracted, 1 hedged)

Sarah Longwell: Trump’s Failures Give Democrats a Once-in-a-Generation Opening | Bulwark on Sunday asserted

Failures → give → Sunday

Bill Kristol and Sarah Longwell discuss Longwell’s new book, How to Eat an Elephant: One Voter at a Time, tracing the origins of The Bulwark and their efforts to oppose Trump while drawing lessons from years of voter focus groups. asserted

Kristol → discuss → groups

They consider how the media environment has changed, what Democrats can learn from Republican political infrastructure, how a broad pro-democracy coalition can manage internal disagreements, and what a successful strategy against Trumpism could look like. uncertain

strategy → consider → Trumpism

Help others find Bulwark on Sunday: hit that like 🤍 button and restack it. asserted

others → help → it