Bill Kristol: Trump's Iran Disaster Is Also a Defeat for the U.S.

Summary of Bill Kristol: Trump's Iran Disaster Is Also a Defeat for the U.S.

by The Bulwark

29mMay 25, 2026

Overview of Bill Kristol: Trump's Iran Disaster Is Also a Defeat for the U.S.

Tim Miller and Bill Kristol spend most of this abbreviated Memorial Day episode unpacking the fast-moving Iran situation and arguing that, whatever deal emerges, it should be understood as a U.S. defeat rather than a victory. They also discuss the Trump coalition’s reaction to the crisis, the prospect of lingering energy and security fallout, the administration’s use of the DOJ against political enemies, Trump’s health, Democratic Party leadership troubles, the Texas Senate race, and a reflective close on Memorial Day and military sacrifice.

Iran, Trump, and the Likely “Deal”

What Kristol thinks is happening

  • Trump clearly wants an Iran deal and wants out of the escalation.
  • The Iranians understand this and are squeezing for leverage while still leaving Trump enough political cover to declare success.
  • Kristol says the likely end state is a murky deal, not a clean resolution.

Why Kristol calls it a defeat

He argues that none of the administration’s original goals are being achieved:

  • No regime change in Iran
  • No liberation of the Iranian people
  • No clear nuclear resolution
  • No strong, durable guarantee on the Strait of Hormuz
  • No decisive weakening of Iran’s regional power

His bottom line: even if the deal is preferable to a broader war, it still amounts to a loss of ground for the U.S.

Lingering consequences

  • Oil and gas markets may remain unsettled for weeks or months.
  • Shipping through the Strait of Hormuz may not normalize quickly.
  • Iran will likely keep flexing its ability to disrupt trade and remind the world of its leverage.
  • Trump’s ability to credibly threaten force is diminished.

The Political Fallout Inside the Trump Coalition

Hawks vs. America First

  • The initial reaction from pro-war Trump allies was anger and panic.
  • Kristol expects most of them to eventually fold back into support and rationalize the outcome.
  • But he and Miller note that the coalition may be more fractured than usual because:
    • America First voices will claim vindication.
    • Traditional hawks may not all be willing to spin this as a win.
    • Some Republicans outside the Trump core seem less willing to fall in line.

Israel and the Abraham Accords

  • Trump appears to be trying to “sweeten” the Iran deal by invoking the Abraham Accords.
  • Kristol is skeptical that this will amount to much:
    • Saudi Arabia is unlikely to join without movement on Palestine.
    • Egypt already has its own peace arrangement with Israel.
    • Trump’s effort to fold Iran into this framework struck the hosts as unserious and awkward.
  • They also note reports that Israeli officials were unhappy with the contours of the deal.

DOJ Weaponization and Cuba

Subpoenas targeting anti-war activists

The hosts flag subpoenas reportedly served to:

  • Hasan Piker
  • Medea Benjamin of Code Pink

The probe concerns their aid trips to Cuba.

Why it matters

  • Miller argues this fits a broader pattern of Trump using the DOJ against people he views as politically expendable.
  • Kristol adds that this may also be part of a larger Cuba escalation:
    • Rubio has been calling Cuba a national security threat.
    • A crackdown on Cuba critics could be groundwork for a tougher policy.

Trump’s Health and Diminished Capacity

What they notice

  • Trump is scheduled for another medical checkup at Walter Reed.
  • The hosts note:
    • multiple Walter Reed visits in a short span
    • two dental visits in Florida
    • visible bruising and signs of physical decline

Why it matters politically

  • Miller sees Trump’s diminished health as especially relevant during a high-stakes foreign policy crisis.
  • Kristol suggests it could make Trump either:
    • more risk-prone, or
    • somewhat more politically sensitive if he fears he may not be around for another campaign.

Democratic Party Troubles and Ken Martin

DNC leadership concerns

  • The conversation turns briefly to reporting about a list of possible replacements for DNC chair Ken Martin.
  • Kristol and Miller are skeptical of the current party setup and emphasize that the key issue is fundraising credibility.
  • Their view:
    • the DNC needs a leader donors trust
    • competence and communications discipline matter more than internal factionalism

Texas Senate Race and Other Electoral Notes

Texas

  • They discuss the Republican primary in Texas, where John Cornyn is expected to lose to Ken Paxton.
  • Miller notes Republicans are already spending money against Democrat Colin Allred-style opposition in the state, signaling concern.
  • Kristol and Miller both see this as a sign of how much the political environment has shifted.

Broader takeaway

  • A year ago, aggressive GOP spending to protect Texas would have looked very different.
  • The fact that it’s happening now suggests the map is less secure than it once seemed.

Memorial Day Reflections

The key message

The episode closes with a serious reflection on Memorial Day and military sacrifice.

What they emphasize

  • Veterans understand Memorial Day differently than civilians do.
  • It is not just “one day a year” for those who served or lost comrades.
  • Kristol recommends reading pieces by:
    • Mark Hertling
    • Will Selber
    • and listening to their interview with Michael Wood

Tone and meaning

  • They describe Memorial Day as one of America’s most sincere traditions:
    • cemetery flags
    • local parades
    • Arlington ceremonies
    • modest, respectful remembrance
  • Kristol contrasts that with Trump’s performative, flashy style and says the holiday should be about humility and remembrance.

Main Takeaways

  • Trump is likely headed toward an Iran deal, but Kristol sees it as a strategic and political defeat for the U.S.
  • The administration’s original Iran goals have mostly collapsed.
  • The fallout may continue through higher energy prices, uncertain shipping lanes, and unresolved nuclear tensions.
  • Trump’s coalition may show cracks, even if many hawks eventually resume spinning for him.
  • The DOJ subpoenas and Cuba posture fit a broader pattern of selective political targeting.
  • Memorial Day, the hosts argue, should be a day of sober remembrance rather than spectacle.