Bulwark Takes

Episode: Bill Kristol and JVL on Dick Cheney’s Legacy
Date: November 4, 2025
Host: The Bulwark (JVL, Bill Kristol)

Episode Overview

This episode of Bulwark Takes is a timely reflection on the legacy of Dick Cheney, who has just passed away. JVL and Bill Kristol engage in a deep, candid conversation about Cheney’s extraordinary influence on American politics spanning five decades. The discussion critically examines Cheney’s career trajectory, his personal attributes, his political evolution, and his complicated public image—from consummate inside operator, to George W. Bush’s “Darth Vader,” to a voice of conscience during the Trump era. Both hosts reveal personal anecdotes and provide keen insights into Cheney’s substance, style, and the lessons that can be drawn from his long life in public service.

Key Discussion Points & Insights

1. Cheney’s Unlikely Rise (00:59–04:00)

• Self-Made Ascent:
  JVL opens by highlighting Cheney’s origins:

  "Cheney sort of comes from a very different place... Very much a self made guy. Comes out of Wyoming, small state with no electoral importance..." (00:59)

• Early Achievements:
  Bill Kristol notes Cheney became White House Chief of Staff at just 34 and had no family dynasty to lean on:

  "He is White House chief of staff at age 34 and ends up in his 80s being a major force as a Republican... So that's 50 years really right in the public eye." (01:52)

• House Leadership:
  Cheney quickly advanced in Congress, becoming #3 in leadership within two terms—a testament to his inside-game skills and seriousness, not charisma.

2. The Multiplicity of Cheney’s Public Image (04:00–05:44)

• Generational Lens:
  JVL points out how Cheney’s persona shifted with the times:

  "If you came of age during the Bush presidency...Dick Cheney is Darth Vader...If you came of age during the Trump years, he is this voice of conscience..." (04:00)

• Multiple ‘Acts’:
  Cheney is among the rare figures to play several defining roles over a very long public career.

3. Cheney, the Power Broker Who Never Ran for President (04:59–08:00)

• Comparison to Other ‘Nearly Presidents’:
  Kristol notes:

  "There's this category of people who never became president, but who are extremely important in American history. And it goes all the way back to Henry Clay..." (04:59)

• Cheney chose not to run, despite encouragement to do so in 1996 after being a highly regarded Secretary of Defense.
• Contingency in Politics:
  The outcome of Cheney’s career hinged on unexpected turns—such as his appointment as Secretary of Defense when John Tower's nomination failed.
• Merit over Politics:
  Kristol underlines that Cheney’s selection as Bush’s running mate was about “help to govern,” not electoral calculus.

4. Vice Presidential Archetypes & Comparisons (08:00–09:47)

• Shifting VP Strategies:
  JVL notes Cheney’s selection started a trend—vice presidents picked more for governing than for succession/ambition.
• Kristol compares Joe Biden’s experience to Cheney’s as providing “a sound hand...someone who understands how the federal government works.” (08:36)
• Obama’s compressed political arc is contrasted with Cheney’s long-term influence.

5. The Substance of Cheney’s Public Service (09:48–12:12)

• Respected, Not Always Agreed With:
  Kristol emphasizes that Cheney was “respected by everyone and taken seriously by everyone,” not a “self-promoter.”
• War on Terror Debates:
  There were policy disagreements—even among allies—especially with McCain on Guantanamo and war conduct, but Cheney’s positions were driven by public service, not personal advancement.

6. Cheney’s Integrity in the Age of Trump (12:12–14:12)

• ‘He Meant It All’:
  JVL makes a core claim:

  "You can be on the fence as to whether or not you believe Cheney meant it all until the Trump Years...the Trump years prove that he, I mean, whereas many of the old guard...they went like W has never said anything publicly, right, about Trump. ...I think Cheney's the only one from that generation who really publicly came out against and said, no, this is dangerous." (12:12)

• Liz Cheney Parallel:
  Kristol notes Dick Cheney’s open break with Trump was tied closely to his daughter Liz’s moral stand, emphasizing familial influence and consistency.

7. Personal Character & Public Persona (15:24–20:49)

• Never Caricatured Himself:
  Cheney defied the modern urge to become a social media “character.” JVL highlights the contrast:

  "...the idea of Dick Cheney tweeting is almost impossible to...or Dick Cheney is a shitposter. Very hard to...see any of that." (15:24)

• Private Dick Cheney:
  Kristol notes Cheney’s wry humor, candor, and loyalty—especially within his inner circle and family.
• Reflective & Well-Read:
  Cheney admired history and literature, and was deeply invested in civic responsibility and the burdens of leadership.
• Common With McCain:
  Both men were multi-faceted, serious, and “not one-dimensional figures.”

8. Legacy and What Public Service Means (20:49–24:02)

• Integrity and Seriousness:
  JVL sums up Cheney’s approach:

  "The guy was not positioning. He was not...it was not kayfabe for him. It wasn't team politics either...He was thinking seriously about America as a place and history as a thing that happens and making his best judgments." (20:49)

• A True Public Servant:
  Kristol links Cheney to Teddy Roosevelt’s “man in the arena”:

  "He fought hard for what he believes he got in the arena. He took the blows, he behaved honorably and an impressive man." (22:17)

• Contrast with the Present:
  JVL offers a pointed comparison:

  "If you want to understand what Cheney was, think of J.D. Vance. And everything goes the exact opposite. That that's what Dick Cheney was." (23:16) Cheney defined meaning and conviction; present figures, in their view, are often defined by posturing.

Notable Quotes & Memorable Moments

• On being a self-made political figure:
  Bill Kristol:

  "It is really a remarkable career. One shouldn't lose sight of that. Just that side of things in addition to everything else he then did substantively in his different positions." (03:32)

• On Cheney’s multifaceted legacy:
  JVL:

  "So if you came of age during the Bush presidency...Dick Cheney is Darth Vader and ...this evil figure...If you came of age during the Trump years, he is this voice of conscience..." (04:00)

• On conviction and public service:
  JVL:

  "...whatever else you want to say about Dick Cheney, he meant it. Right? ...He wasn't just wearing the jersey. He was thinking seriously about America..." (20:49)

• On Cheney during the Trump era:
  JVL:

  "I think Cheney's the only one from that generation who really publicly came out against and said, no, this is dangerous." (12:44)

• On what separates Cheney from modern politicians:
  JVL:

  "If you want to understand what Cheney was, think of J.D. Vance. And everything goes the exact opposite." (23:16)

• On public service:
  Bill Kristol:

  "We use that term public servant all the time…but he really was a public servant." (22:18)

Timestamps for Key Segments

• Cheney’s Determined Rise & Early Career: 00:59–04:00
• The Many 'Acts' of Cheney’s Public Life: 04:00–05:44
• Significance Despite Never Running for President: 04:59–08:00
• Starting the Modern VP Trend (for governing, not winning): 08:00–09:47
• His Substance & Disputes (Guantanamo, War on Terror): 09:48–12:12
• Meaning It During the Trump Years: 12:12–14:12
• Personal Side & Private Character: 15:24–20:49
• The Final Word on Legacy & Contrast with Today’s Politics: 20:49–24:02

Tone & Takeaway

The episode’s tone is reflective, respectful, and keenly analytical, occasionally wry but always serious about the weight of Cheney's career. Both hosts, despite differences with Cheney on policy, acknowledge his seriousness, substance, and underlying integrity—a foil for much of today’s political culture. The discussion insists that, for all his controversies, Cheney’s courage of conviction and stamina in serious public service deserve special recognition as his legacy comes to a close.