In the months leading up to the 2003 invasion of Iraq, I served as a strategist at the Pentagon, where I had unusual access to military thinking, intelligence assessments, and senior-level discussions. I regularly attended meetings hosted by Secretary of Defense Donald Rumsfeld and Chairman of the Joint Chiefs General Richard Myers.
From the outside, it looked like Washington spoke with one confident voice. The Bush administration telegraphed certainty, and much of the media echoed it.
That was not my view.
The more information I received, the more questions I asked. What would victory look like? How many troops would be required? What would follow after Baghdad fell? Were we prepared for a prolonged occupation? Did we fully understand the political, tribal, religious, and regional forces we were about to unleash?
PRESIDENT TRUMP’S IRAN WARNING IS SERIOUS — BUT AMERICANS NEED THE FULL FACTS
Those questions were swept aside by confidence in America’s military superiority.
The regime fell quickly. The war did not.
What followed cost America more than 4,400 military deaths, over 32,000 wounded, and more than two trillion dollars. The conflict created the conditions that gave rise to ISIS, a threat that still plagues the region.
One hundred days into the Iran war, I find myself asking many of those same questions again.
THE CEASEFIRE THAT ISN’T
The fragile pause that began in early April has unraveled. On June 9, an Iranian Shahed drone struck a U.S. Army AH-64 Apache helicopter patrolling near the Strait of Hormuz — the first Apache loss of the conflict. Both crew members were rescued and are safe. President Trump immediately declared on Truth Social that “the United States must, of necessity, respond to this attack.” U.S. Central Command launched retaliatory strikes the same day.
Iran answered by targeting U.S. military bases in Bahrain, Kuwait, and Jordan — the second consecutive day of Iranian strikes on American positions in the region.
A second wave of U.S. strikes hit “multiple targets” in Iran on June 10. The Strait of Hormuz — the chokepoint that carries 20 percent of global oil — remains contested. Brent crude climbed to $91.10 per barrel Wednesday. The S&P is down 4.5 percent from its June 2 record high.
Even as the bombs fell, Trump told reporters a deal was “two or three days” away and that the Strait would reopen “immediately” once Iran signed. The Iranian parliament speaker said Trump’s public statements “contradicted the agreed-upon sections,” signaling that Tehran sees no agreement close at hand.
The administration’s theory is understandable. Increased costs will eventually convince Tehran that compromise is preferable to continued punishment. History suggests the matter is not that simple.
PATTERN WASHINGTON KEEPS MISSING
Iran has responded as it has for nearly half a century. It negotiates. It delays. It demands concessions. It links one issue to another. It seeks leverage while avoiding irreversible commitments.
In recent Fox News columns, I have argued that Washington’s greatest misunderstanding of Iran is the assumption that the regime thinks as we do. America seeks resolution. Tehran seeks survival. America wants closure. Iran wants time.
The 60-day MOU framework that emerged in late May offered Iran the ability to sell oil freely, a moratorium on enrichment in exchange for sanctions relief, and a path to nuclear talks. Tehran’s foreign minister called a deal “just inches away” while simultaneously accusing U.S. negotiators of “maximalist demands.”
That pattern — advance and obstruct, concede, and reclaim — has defined Iranian diplomacy since 1979. It should not surprise anyone in Washington. The surprise is that we keep expecting a different result.
TRUMP’S IRAN WAR NOW COMES DOWN TO ONE BRUTAL QUESTION: WHAT COMES NEXT?
Iran’s foreign minister put it plainly after the Apache was downed: “Foreign forces in proximity to our territory are at constant risk. To reduce risk, best solution is for them to leave.”
That is not the language of a government preparing to sign a final agreement. It is the language of a government buying time.
THREE CHOICES, EACH WITH A PRICE
President Trump now faces three stark choices, and each carries costs Washington has yet to honestly acknowledge.
The first is escalation. If the objective is the permanent elimination of Iran’s nuclear program and Tehran refuses to surrender it, the logic eventually points beyond airpower to something far larger. Iran is not Iraq in 2003. It is larger, more populous, and more difficult geographically. Mountain ranges dominate much of the country. Tehran sits deep inland. The force required would dwarf even what we assembled for Iraqi Freedom in 2003 — and that coalition included the British, Australians, Poles, and dozens of other contributing nations. No comparable alliance exists for a war with Iran. Europe would sit this one out. That means mobilizing not just the active force but much, if not all, of the National Guard and Reserve components, without the allied burden-sharing Washington had in Iraq. That arithmetic has not been put before the American people.
Capturing Tehran would be difficult. Holding it would be a generational commitment. Determining what follows would be harder still.
The second is long-term containment. This accepts an uncomfortable reality: Iran may never willingly negotiate away what its rulers consider a strategic necessity. Containment combines military deterrence, sanctions, maritime security, intelligence operations, and stronger regional partnerships. It requires patience rather than dramatic declarations. It lacks the appeal of decisive triumph, but it may better reflect the realities of confronting a regime that measures time in decades rather than election cycles. We held the Soviet Union at bay for fifty years through exactly this approach — containment reinforced by mutually assured destruction. The Soviets had thousands of nuclear warheads and the means to deliver them. The strategy worked not because we liked the odds, but because we were honest about them. The same discipline applies here.
The third is an armed truce, which is what Trump is still pursuing. Negotiations continue despite the renewed strikes. But any agreement must be judged by results, not promises. A deal that pauses the fighting while leaving the core dispute unresolved does not solve the problem. It postpones the next crisis — and likely at higher cost.
In my books Preparing for World War III and Kings of the East, I argued that America’s principal adversaries think in generational terms. China does. Russia does. Iran certainly does. They absorb setbacks today to improve their position tomorrow. Every week of ceasefire that does not produce irreversible denuclearization is a week Tehran uses to reconstitute, reposition, and wait out Washington’s political calendar.
THE QUESTION THAT STILL HAS NO ANSWER
The president’s challenge is not a lack of military options. The United States remains the world’s most capable fighting force. The challenge is defining an achievable political objective and being honest with the American people about what it costs.
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If the goal is regime-ending victory, the American people deserve a frank accounting of the scale, duration, and human cost of that commitment.
If the goal is containment, Washington must stop suggesting that additional bombing runs will force Tehran’s surrender.
If the goal is a negotiated settlement, verification must matter more than optimistic timelines. An Iran that agrees today and reconstitutes tomorrow is not a solved problem.
The hardest question facing President Trump is the same one I asked while sitting inside the Pentagon before Iraq.
Not whether America can win battles. We can.
Not whether America can destroy targets. We can.
The real question is what political outcome justifies everything that comes afterward — and whether we are prepared to be honest about the answer before the next Apache goes down.
Wars of choice begin with confidence. They end when leaders finally confront the choices they hoped to avoid.
