My Kingdom for an Off-Ramp!: Donald Trump Looks for an Exit

Seventeen years ago, Mahmood Ahmadinejad, then the Iranian president was dominating western headlines. But even then, concentrating on his vitriolic statements was a mistake. One needed to concentrate on the pronouncements and actions of the one person who really counted in that regime Supreme Leader Ali Khamenei, who was then 69 and widely believed to have cancer.

As we know, Khamenei did not die then. Not until two weeks ago, when U.S. President Donald Trump and Israeli Prime Minister Benjamin Netanyahu did what nature had not and ended the supreme leader’s 36-year stewardship of the Islamic Republic. Khamenei left a problematic legacy. Since his1989 ascension to power, the Iranian rial essentially lost almost all of its value against the dollar. Although endowed with considerable natural resources, Iran consistently experiences electricity and water shortages even as past year, food prices surged more than 70 percent over the past year.

These economic woes are in large part the consequence of a foreign policy almost singularly focused on countering U.S. interests. When faced with popular discontent, Khamenei consistently resisted even token reforms and resorted to sheer violence to repress his people—most notably in January, when his regime murdered thousands (perhaps as many as 30,000) of its citizens. But he clearly has strategic sense, investing time in preparing Iran for just a maximum danger moment like this. Confronted with a truly existential threat to its very existence, Iran’s regime has mounted a much more deliberate, decentralized, asymmetric and effective response than many armchair generals expected, striking not only Israeli territory and U.S. diplomatic and military installations but also civilian targets throughout the Persian Gulf, including airports, hotels, and energy infrastructure – an approach calculated to apply pressure on world where it counts the most: economic security.

It’s a safe bet that Trump wants to declare victory soon, and he is likely to seize upon any event which allows him even an iota of chance to ‘spin’ as a successful narrative. The Iranian military has been severely degraded, much of its clerical and IRGC leadership decimated but conversely this has allowed a hitherto compliant armed forces to assert themselves. Israel could be running low on missile interceptors for its Iron Dome, and keeping global markets stable will require international cooperation to reopen or reduce the potential of damage to shipping transiting the Strait of Hormuz, which Iran has declared closed to its enemies. But the American president is cannot simply force surrender on a government that refuses it. Whomever is left of the band Khamenei put in place has powerful incentives to pursue continued conflict, and it retains a variety of tools to sustain a prolonged war of attrition.

The conflict is thus barreling toward an inflection point at which all the potential options are negative. To agree to a any cease-fire, Tehran will almost certainly demand assurances that the U.S. will constrain future Israeli strikes, and this is not merely a face-saving condition. Like most presidents, Trump retains substantial leverage over Netanyahu because of Israel’s dependence on U.S. military assistance, but it is still a huge ask with potential implications. Very soon, if not already, he will face a choice between doubling down on an unpopular war or, to end it, wresting a concession from Israel that Iran could frame as nothing less than a triumph, much less a moral victory.

Well You Broke It...

Despite the clear tactical brilliance of its joint offensive with Israel, strategic success remains elusive for the U.S. Trump went to war against a country of 92 million people with no clear plan for an endgame. He initially declared that victory would be achieved if the Iranian people rose up and dismantled the Islamic Republic themselves—an extraordinary and unrealistic request. There had been precedent: the regime’s horrific crackdown in January produced no meaningful defections from the regime or security services, and government leaders have already shown they are willing to kill as many of their own people as needed to stay in power.

The United States has failed to understand that an equal number of Iranians to those seeking freedom from the government’s yoke are prepared to die for the regime along with simple but likely true observation that most Iranians just wanted a better day-to-day life. It would be helpful to think of this situation as a 20-20-60 ratio: Twenty percent of Iranians are dedicated to the downfall of the Islamic Republic; 20 to its preservation, and the remainder to a better life. That would be a more realistic approach than using Hollywood movies (akin to the Top Gun style triumphalist videos the White House was putting out recently).

Many in the West long assumed that after Khamenei died, the Iranians who wanted a better life would join forces with those strongly opposed to the Islamic Republic to force the country’s leaders down a different path than the one the supreme leader had charted. But the bitter irony is that the U.S. and Israeli approach to the recent war afforded Khamenei something he seems to have wanted --a martyr’s death— which proved a gift to the regime, as it diverted attention away from the Islamic Republic’s failures. It elevated Khamenei’s hardline son (assuming he’s actually alive) and turned much of the nation’s focus toward surviving an external assault. All these outcomes only served to marginalize the silent majority of Iranians who just want a measure of well-being.

Wars are not just won on the battlefield: that’s merely the most overt manifestation of conflict where the results of a zero-sum game is obvious. But this war is more than that. Iran does not need to score major military successes every day. The regime only needs to inflict enough periodic damage to keep regional partners, markets, and the American public jittery. Despite undeniably catastrophic damage to the Iranian navy and other branches of their armed forces, periodic drone attacks (which are comparatively cheap) on tankers attempting to traverse the Strait of Hormuz are probably enough to keep traffic snarled in a shipping channel responsible for a fifth of global oil supply. It’s the modern-day variation of Vietnam’s insurgent approach when taking on the vastly superior technology the U.S. employed.

There are, of course, substantial risks to pursuing this strategy. It could unite the Gulf countries against Tehran and invite further escalation (although another school of thought hold that an apocalyptic outcome where nations are drawn into the war like a latter-day Götterdämmerung). That Iran is thinking on calculated terms is manifested in its holding some offensive capabilities in reserve. This may be why it has not asked for more of the Houthis in Yemen, undertaken broad cyberattacks, or mounted acts of terrorism on U.S. interests outside the Middle East and even on American soil. But Khamenei obviously gambled that even if he died, his regime could handle more losses than the United States or the Gulf states could. It’s the old Mao Zedong philosophy of having sufficient population to outlast our foe’s zeal for war.

Between Iran and a Hard Place

Although the parallel is imperfect, Israel’s current tactics and objective appear to resemble the ones that undergirded its 2024 campaign to neutralize Hezbollah in Lebanon. That effort included a series of decapitation strikes on Hezbollah’s leadership and a swift degradation of the militia’s ability to wage war on Israel. Israel parlayed those tactical gains into a status quo that allowed it to periodically “mow the grass,” continuing to strike the organization as needed with few repercussions and relative impunity. While Israeli leaders understand that Trump may seek to speedily end this particular conflict, they will still have to ‘live in the neighborhood ‘after the U.S. declares victory and therefore cannot be content in the long term with a cease-fire that largely leaves the Islamic Republic in place. Thus, tt will be only a matter of time before they attempt to reinitiate conflict and further weaken Iran. For both Tel Aviv and Tehran, this is literally a deathmatch.

As noted before in previous posts, Donald Trump appears more focused on creating his legacy (as most presidents in their second and final term do) than on any specific objective, His periodic references to his “little excursion” in Iran echo a 1898 boast in by U.S. Secretary of State John Hay that his country’s four-month conflict with Spain had been a “splendid little war” that demonstrated American power and glory. At some point, the toll on the U.S. arsenal (‘smart’ missiles and bombs might be devastatingly effective but that effectiveness has a cost which makes resupply prohibitively expensive), and the global economy will demand that Trump bring the show to a close. Keen to avoid Hezbollah’s fate, however, the Islamic Republic is not seeking an off-ramp. Iranian leaders want to extend the war as long as possible and make both POTUS 47 and subsequent U.S. presidents less eager for a future conflict.

Trump could continue to prosecute the war in Iran by persisting with his devastating aerial campaign, but this is already yielding diminishing returns, given that the U.S. military has already struck most of its targets. The alternative is to put American boots on the ground, which comes with awful risks and is precisely what Trump, as a presidential candidate, repeatedly pledged never to do. But it may well be the only way to ensure an Iranian regime more amenable to his demands. Trump may also consider smaller, more targeted operations related to maritime security or Iran’s nuclear program, perhaps even seizing Kharg island, where 90% of Iran’s oil products are exported from, as well as supplying storage for up to 30 million barrels (5 million cubic metres) of oil. But these, too, would pose significant risks to American soldiers and likely prompt retaliation—and there is little chance that they would actually lead to Iran’s capitulation.

We Didn't Start the Fire...

A ‘cheaper’ alternative would be Trump effectively outsourcing the war by arming political or ethnic factions that oppose the Tehran regime. That might prove a calamitous option: mobilizing the Kurds or any other ethnic separatist group would keep many anti-regime Iranians at home and fragment the opposition. While such a move could result in the deaths of a few more Iranian soldiers, it would not diminish the regime’s ability to repress internal dissent. It might actually risk exacerbating regional conflict and driving uncontrolled mass migration into Turkey, Iraq, Afghanistan and Pakistan. Worse, it could lead to an Iranian civil war as its society fractures along sectarian lines, pitting Kurds, Sunni and Shia Muslims against each other in a regional conflagration of worse proportions than seen so far.

That leaves one option: try to achieve a formal cease-fire. Theoretically, of course, Trump could simply declare that the degradation of Iran’s military and the killing of Khamenei constitute victory and walk away, but this is harder than it sounds. He cannot unilaterally stop Tehran from attacking U.S. assets or the Gulf states. Iran would rather fight a protracted war with the United States now than repeated wars with Israel in the coming years. Even if the United States unilaterally withdraws from the fight, if a future Iran-Israel conflict looks inevitable, Iran will likely continue targeting U.S. interests in the region as well as the Gulf states and energy infrastructure.

Basically, the situation is a mess with few if any palatable options for the American president. Iran’s strategic objective now is to impose such high costs on the U.S. and the Gulf states that driven by domestic concerns and plunging popularity, Trump will have no choice but opt for a cease-fire that includes some sort of restriction on future Israeli actions. In essence, Iran wants to force him to choose between Israel’s security interests and the stability of global markets. The bottom line is that the war Trump started has no good ending or easy off-ramp and every day it goes on seems to delay a better future for the Iranian people. This is a tragedy that only Khamenei and Trump, together, could have engineered.