Bulwark Takes: "Tom Nichols: There Are 500 Ways This War Goes Wrong"

Host: Mona Charen

Guest: Tom Nichols

Date: March 3, 2026

Episode Overview

On this urgent special edition of the Mona Charen Show (presented within Bulwark Takes), Mona is joined by Tom Nichols, former Naval War College professor and Atlantic contributor, to break down the U.S.-led war against Iran. They candidly explore the immense risks, possible outcomes, the administration’s lack of preparation, the historical record of “regime change” wars, and the constitutional and geopolitical challenges at stake. Nichols’ central warning: while some hope exists for a positive outcome, there are "500 ways this war goes wrong," and America is perilously unprepared for most of them.

Key Discussion Points & Insights

1. The Best Case – and Why It’s Improbable

[01:00 – 05:00]

• Nichols: “The President is trying to draw to an inside straight … look, that can happen, but that’s not the way to bet.”
• The best case (the regime falls, replaced by something better) is possible but highly unlikely.
• Genuine regime collapse would require armed security forces to defect en masse to an organized opposition—a dynamic absent in Iran today.
• Nichols and Mona agree that simple bombing, no matter how targeted, doesn’t create a power structure for opposition groups.

2. Lessons from Previous Regime Change Efforts

[06:00 – 15:00]

• Libya Comparison: Obama’s strategy involved no boots on the ground, hoping rebels would take advantage of the weakened regime. But Libya already had armed rebel groups, unlike Iran.
• Iraq (1991 & 2003): In both Gulf Wars, U.S. leadership called for locals to rise up—often with catastrophic consequences, e.g., “tens of thousands of people died” ([12:33], Nichols).
• Memorable Quote:
  “There are 500 ways to do this wrong and only two or three ways to do it right. … What I didn’t count on was that we were going to do all 500 ways first.” — Barbara Bodine, quoted by Nichols ([09:54])
• Kosovo as Anomaly: The successful NATO bombing was focused, specific, and immediately followed by a robust peacekeeping presence—nothing like the Iran scenario.

3. The Many Ways This Can Go Wrong

[10:25 – 16:42]

• Country could fracture into mini-dictatorships or juntas.
• Replacement leadership might be “just as bad or worse.”
• Foreign powers, especially China, could seize the post-war vacuum.
• The administration hasn’t built infrastructure for even a best-case transition.

4. The Fallacy of “No Rules of Engagement / No Nation-Building”

[15:49 – 19:43]

• Discussion of Defense Secretary Pete Hegseth’s tough-guy rhetoric: “no stupid rules of engagement,” “no nation building quagmire.”
• Nichols (mocking Hegseth): “Yeah, sure, we’re going to send up a bunch of strike aircraft, say, all right boys, weapons, do whatever. … That’s not how any of this works.” ([17:33])
• Even purely air campaigns require rules for targeting and collateral damage.
• Real situations (Somalia’s child soldiers) demonstrate the moral and psychological toll of ill-conceived rules.

5. The Endurance of Repressive Regimes

[19:43 – 22:05]

• Iran’s rulers are skilled at absorbing pain: “This is a regime that just killed between 30 and 40,000 of its people simply for the crime of protesting in the streets.” — Charen ([19:43])
• The regime may survive punishment and only double down on nuclear ambitions to prevent future attacks.

6. Nuclear Weapons & the “Security Dilemma”

[21:42 – 24:39, 52:04–54:47]

• Destroying regime may push future Iranian leaders to seek nukes more aggressively.
• Nichols: “Hope’s not a strategy.” ([24:39])
• Even if nuclear sites are destroyed, regime survivors may look to North Korea as a model for deterrence.

7. The Value and Absence of Allies

[27:34 – 31:39]

• Israel is America’s sole ally in this conflict; most traditional partners are absent.
• Looks like the U.S. is “the junior partner” to Israel—a dangerous perception.
• Memories of Gulf War coalitions (40+ countries) contrast starkly with U.S. and Israel alone.
• Risk of China or other adversaries filling the void postwar.

8. Strategic, Legal, and Constitutional Perils

[33:09 – 39:24]

• Trump’s disregard for Congressional approval marks a dramatic break from all other modern presidents, even for limited interventions.
• Nichols: “He’s just giving the finger to his own constituency. His base is not behind him on this.” ([41:53])
• Congress must demand a reckoning: “You need to come to us as the representatives of the American people.” ([39:38])

9. Trump’s Management Style – Simple-Mindedness and Narcissism

[42:11 – 44:49]

• Trump’s guiding assumption: everything is easy unless you’re “stupid.”
• Repeatedly claims to invent concepts or policies already well-known (e.g., “I call them groceries”).
• Nichols: “It’s funny when you’re talking about groceries. It’s not funny when you’re talking about a major war in the Middle East.” ([44:39])

10. The Most Likely Outcome

[45:04 – 48:35]

• Charen: U.S. may end up supporting a “bad person” from the existing regime, rebranded but essentially the same, now rushing for nukes.
• Nichols: Unlikely Iran will go nuclear immediately; more probable is a tactical pause, but U.S. will have only stalled the program at great cost.

11. The American System at Risk

[55:19 – 57:37]

• The “mad, violent king” problem: America, designed to avoid kingly power, now finds itself under a president waging war by fiat.
• Risk of Trump using war powers domestically to stifle dissent: “Dissent will be considered unpatriotic and harming the troops.” — Charen ([57:43])

Notable Quotes & Memorable Moments

• “There are 500 ways to do this wrong and only two or three ways to do it right. … What I didn’t count on was that we were going to do all 500 ways first.” — Amb. Barbara Bodine, quoted by Nichols ([09:54])
• “We’re going to just bomb the hell out of everything and then we’re going to see what happens.” — Nichols ([11:24])
• “If we win this war, it’s going to take a lot of people to help... There has been no depth of thinking about this.” — Nichols ([29:15])
• “The only way to prevent the Iranians from wanting a nuclear weapon is if there were a real change of government, a change of who runs the place, who has the power.” — Charen ([52:04])
• “Hope’s not a strategy.” — Nichols ([24:39])

Important Timestamps

• 01:59 – 05:02: Setting the odds for best-case/worst-case war outcomes
• 09:45: Bodine’s “500 ways to do it wrong” Iraq quote
• 12:33 – 14:47: Iraq, Kosovo, and the history of “regime change” by bombing
• 17:07 – 19:43: Hegseth, rules of engagement, and how real officers think
• 21:42 – 22:05: Iran’s likely reaction—rush for nukes
• 27:49 – 31:39: Geopolitics of fighting with only Israel as an ally
• 33:09 – 39:15: Congress’ power and Trump’s indifference to legal/constitutional norms
• 44:39 – 44:49: The gravity of Trump’s simplistic approach in the context of major war
• 45:04 – 48:35: Predicting the most likely outcomes
• 52:04 – 54:47: The nuclear question and why airstrikes alone can’t prevent it
• 55:19 – 57:37: Erosion of constitutional checks; domestic risks of war powers

Closing Thoughts

Tom Nichols and Mona Charen, with clarity, draw on decades of foreign policy experience to lay out the stunningly high risks and the frightening lack of planning or support for this war. Their warnings—on both practical and constitutional grounds—are conveyed with dry wit and deep concern. The episode is an indispensable guide for understanding not just the situation in Iran, but the broader crisis facing American governance and international standing as the nation stumbles into possibly its most consequential military adventure of the century.

For listeners who missed the episode, this summary captures both the gravity and urgency of the conversation, and the indelible skepticism Nichols and Charen bring to the unfolding events.