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The Free Press

Trump’s Endgame

Through the fog of war, it’s possible to see where all this is heading.

michael_doran
michael_doran
Senior Fellow and Director, Center for Peace and Security in the Middle East
Michael Doran
President Donald Trump sits at a table monitoring military operations during Operation Epic Fury against Iran on March 2, 2026. (Getty Images)
Caption
President Donald Trump sits at a table monitoring military operations during Operation Epic Fury against Iran on March 2, 2026. (Getty Images)

The fog of war does not prevent us from peering into the future and catching a glimpse of the exact moment when this conflict will end. Donald Trump will pick up the phone and tell Benjamin Netanyahu, “Bibi, it’s time for a ceasefire.” Netanyahu will reply, “Yes, I agree.”

The cooperation between Trump and Netanyahu is unprecedented in U.S.-Israeli history. American and Israeli forces operate as a tightly integrated unit, closer than ever before. Yet the underlying power dynamic remains unchanged from June 2025, when the first U.S.-Israeli joint operation against Iran ended abruptly.

Television cameras captured the moment for posterity. On the White House lawn, a visibly frustrated Trump vented not just at the Iranians but also at the Israelis for not respecting the ceasefire he was trying to impose. “We have two countries that have been fighting so long and so hard,” he said, “that they don’t know what the fuck they’re doing.”

Moments earlier, Trump had ordered Netanyahu to recall Israeli aircraft—already airborne, bomb-loaded, and en route to Iranian targets. Netanyahu complied immediately.

When Trump brings the current war to a close, the conversation will be far more cordial. No public outbursts. Trump will defer to Netanyahu, giving him the final say. But it will be “I agree.”

The Iranians understand this power dynamic. Their strategy, therefore, is to force Trump’s hand sooner rather than later by raising costs at every opportunity—regionalizing the war and generating diplomatic and economic pressure on the United States to end it quickly.

Iranian Revolutionary Guard Corps (IRGC) threats and attacks on tankers have shut down the Strait of Hormuz, through which roughly 20 percent of global oil and liquefied natural gas (LNG) flows. The waterway is now closed in practice: Tanker traffic has collapsed to near zero, major shipping companies including Maersk and Hapag-Lloyd have suspended transits entirely, and more than 150 vessels are anchored outside the strait. Hundreds more are stranded, disrupting global energy flows. Iran has struck key energy infrastructure, including Saudi Arabia’s Ras Tanura refinery and facilities in Qatar such as Ras Laffan, halting LNG production. Oil prices, already in the mid- to high-$70s before the escalation, have surged into the $80s and could easily exceed $100 if disruptions continue.

The United States and Israel likely do not possess enough interceptors to shoot down Iran’s entire stockpile of missiles, which it stores in vast underground “missile cities”—hardened complexes built with North Korean assistance, extensive tunnel networks that are extremely difficult to eliminate. The allied strategy therefore prioritizes targeting launchers, launch crews, and command infrastructure over deep stockpiles: Destroy the archers, because their arrows are out of reach.

Iran’s approach exploits the finite and costly nature of defensive systems like Patriot, THAAD, and Arrow batteries. Relentless barrages of missiles and drones aim to deplete interceptor stockpiles. Systems often commit multiple interceptors to each high-priority threat, especially over civilian areas.

The overriding goal is regime survival. Tehran calculates that it can endure defeat much as Saddam Hussein did after 1991—militarily weakened but still in power. In the modern Middle East, regimes rarely disappear simply because they lose on the battlefield. The Taliban never won a conventional engagement against the United States, yet they rule Afghanistan. Hamas, though devastated militarily, retains influence in Gaza. Hezbollah, severely weakened, remains central to Lebanese politics.

The Iranians are betting that sustained pain—political, economic, diplomatic, and military—will eventually convince Trump to end the campaign and declare victory before toppling the regime. They know he will go to great lengths to avoid putting American troops on the ground. They also know he is reluctant to precipitate a civil war like the one that ravaged Syria and destabilized the region. American self-restraint tells the Iranians that they have a chance to hold on.

Upon entering the war, President Trump made two promises that, while not contradictory, do not fully align in practice. The first promise was concrete. Iran, Trump said, will not possess nuclear weapons; its missile program will be dismantled; and it will cease financing and arming proxies across the Middle East.

The second promise was aspirational. Trump promised the Iranian people freedom and dignity. Regime change, however, requires fracture from within—security forces turning on the leadership, elites breaking ranks, or mass uprising forcing the regime to flee. Thus far, none of this has materialized. The political system remains cohesive. Security forces show no visible defections. While crowds may celebrate Ayatollah Ali Khamenei’s death, public resentment has not translated into a coordinated challenge to the regime.

The core obstacle is the IRGC, which has evolved from an ideological militia into the regime’s backbone. The IRGC operates alongside the regular army but controls missiles, drones, the Quds Force, and the Basij militia responsible for domestic repression. It influences intelligence and controls key broadcasting arms. The judiciary enforces ideological discipline. Even with senior leaders killed and headquarters struck, the system adapts. No single decapitation severs these networks.

But the IRGC is far more than a military force. It penetrates all levels of society. Economically, it functions as a parallel state. Through entities such as Khatam al-Anbiya Construction Headquarters, the Guards control major infrastructure (railways, gas pipelines, dams, oil and gas fields, ports, and energy projects), often through no-bid contracts. The bonyads, quasi-charitable foundations under Supreme Leader patronage, operate as vast conglomerates with tax exemptions, opaque finances, and dominance across industries including agriculture, banking, and real estate.

The IRGC sells oil abroad and operates sanctions-evasion networks. Estimates place IRGC-affiliated activity at a staggering share of national output, perhaps as much as half of Iran’s GDP. It employs millions of people and concentrates loyal constituencies in every major city. In short, dismantling this system means uprooting an entire political economy that took decades to build.

External force alone is therefore unlikely to produce regime collapse. Airpower can degrade capabilities and create openings. But uprooting the IRGC requires internal fracture or sustained mass mobilization—neither of which has yet emerged.

This brings us back to Trump’s two promises. The first—neutralizing nuclear capabilities, degrading missile forces, and constraining proxies—is achievable through sustained military, economic, and diplomatic pressure.

The second—freedom for the Iranian people—depends on Iranians themselves: politicians recognizing that survival requires change; security officers refusing to fire on their own citizens; young people willing to risk confrontation. The United States can shape conditions. It cannot create a revolution by remote control.

Trump is giving himself wide latitude to define the endgame. He has repeatedly said the war will continue until its objectives are achieved. When asked Monday night how he would know when that moment had arrived, he replied: “I know a lot, and I will absolutely know when it’s achieved. It’s getting very close, too. We’re doing a lot of damage, we’re setting them back a lot.” This gnomic confidence is vintage Trump—positioning himself as the ultimate decider while preserving maximum freedom of action.

The first major decision he faces is whether to insist on formal acceptance of all three objectives before declaring a ceasefire—effectively demanding unconditional surrender. Past patterns and his public messaging suggest he will not. Such an ultimatum risks prolonging the war, alienating allies weary of rising energy costs, and inviting domestic backlash over casualties and economic disruption. Trump has already signaled openness to talks with members of the regime, framing negotiation as proof of American dominance rather than weakness.

If Trump announces a ceasefire while the regime remains intact, he will de facto choose regime preservation. Negotiating with the regime to dismantle its capabilities is therefore not merely a diplomatic step—it is a strategic decision to leave that regime in power. This is the most likely outcome. He will point to degraded missile stocks, crippled naval assets, damaged nuclear infrastructure, and weakened proxies as evidence that his concrete promise to the American public, the West, and Israel has been fulfilled. The aspirational promise to the Iranian people—freedom and dignity—would remain unresolved.

But ending the war without securing a path to regime change raises three critical follow-up questions. Does Trump force Tehran to accept, as the price of a ceasefire, all three core demands—nuclear dismantlement, missile elimination, and an end to proxy financing? Does he try to settle for progress on the nuclear file alone? Or does he repeat his behavior of last June and end the fighting before receiving any concrete commitment from the Iranians at all?

Tehran, of course, will seek a ceasefire without binding conditions. If forced to make a concrete concession up front, it will discuss, as it did in the recent talks in Geneva and Oman, nuclear compromises while resisting negotiations on missiles and proxies.

Trump cannot afford to blink here. The endgame requires a comprehensive settlement, not tactical trades.

If Iran dismantles its nuclear program in exchange for sanctions relief while retaining its missile arsenal and proxy networks, the regime will simply rebuild. Hezbollah, Hamas, the Houthis, and Iran-backed militias in Iraq would soon be flush with cash. Tehran has demonstrated repeatedly that it can regenerate these capabilities even under pressure.

All three demands must therefore remain a single package. Ideally, Trump should make a ceasefire conditional on formal, authoritative, and public acceptance of all three. At a minimum, Trump must make clear that no sanctions relief—on any front—will come until there is verifiable agreement on the full set. Anything less would leave the regime intact while allowing it to regenerate the very capabilities the war was meant to eliminate.

Partial concessions would merely postpone the problem, allowing a battered but surviving regime to regroup and threaten the region again. Trump’s “maximum pressure” strategy loses its edge the moment relief arrives prematurely.

Read in The Free Press.