The Five Big Known Unknowns of Trump’s Iran War
Over his career as a New York real estate tycoon, Donald Trump oversaw multiple bankruptcies for his casino properties. Now, in his second presidential term, Trump’s long-standing appetite for high-risk gambits has reached its most consequential pitch yet: the unilateral war of choice he launched against Iran over the weekend stands as the biggest political gamble of his entire time in public life. The reported death of Iran’s long-time supreme leader in the war’s opening airstrikes only amplifies the danger this conflict poses for Trump, his key ally Israeli Prime Minister Benjamin Netanyahu, the entire Middle East region, and the whole world.
On one level, the outbreak of war this weekend felt almost inevitable. Most observers saw this conflict coming for months: the U.S. had been building up its military posture in the region for weeks, and in many ways, Trump has been on this path since May 8, 2018, when he discarded the Joint Comprehensive Plan of Action (JCPOA), the Obama-era nuclear deal painstakingly negotiated to block Iran from developing a nuclear weapon. Similarly, Iran’s immediate retaliation—missile barrages and cross-border strikes targeting U.S. allies across the Gulf, including Kuwait, Qatar, Bahrain, Israel, the United Arab Emirates, Saudi Arabia, and Jordan—was widely anticipated and clearly signaled long before the first airstrike.
But the trajectory of the conflict from here—its duration, its geographic spread, and the future of Iran’s ruling regime in the coming days, weeks, and months—represent some of the most staggering unknowns the notoriously volatile Middle East has ever faced.
All modern history teaches us that upheaval in Iran is the proverbial butterfly effect, with the potential to reshape global politics for decades in ways we cannot yet anticipate. The U.S. is still grappling with the aftershocks of Iran’s last major revolution, nearly 50 years ago, when the American-backed Shah—installed in power by a 1953 CIA-led coup—was ousted by Ruhollah Musavi Khomeini. Khomeini’s successor, Ali Hosseini Khamenei, led Iran for decades until he was killed in joint U.S.-Israeli airstrikes this weekend.
In the lead-up to the 2003 Iraq War—the first major American strategic blunder of the 21st century in the Middle East—then-Secretary of Defense Donald Rumsfeld famously distinguished between “known unknowns” and “unknown unknowns” in geopolitics. Today, breaking down the key known unknowns of Trump’s new venture in Iran helps clarify just how high the stakes are for what comes next.
1. The conflict has already claimed American lives
Over the past year, two high-profile tactical military wins have emboldened Trump’s aggressive global posture: a stealth bomber campaign targeting Iranian nuclear sites last year, carried out in partnership with Israel, that cost no American lives; and the audacious raid to capture Venezuelan leader Nicolás Maduro just weeks ago, which also ended without any U.S. fatalities. But history is never a sure thing, and a recent event revealed just how close that Maduro operation came to catastrophe: at this year’s State of the Union address, Trump awarded the Medal of Honor to Army Special Operations pilot Chief Warrant Officer 5 Eric Slover, who survived four machine gun wounds while piloting the lead MH-47 Chinook helicopter during the raid.
The moment was a transparently staged, TV-friendly event rushed by the Pentagon to fit the president’s political schedule, skipping the usual months-long vetting process. But more importantly, it laid bare that Slover’s courage and quick thinking were the only thing that kept the mission from collapsing. If Slover’s lead helicopter had crashed in the raid’s opening minutes, the operation would likely be remembered not as a bold success, but as a debacle on par with Jimmy Carter’s failed 1980 hostage rescue mission, Operation Eagle Claw, which killed eight U.S. service members and ended Carter’s presidency.
There is little reason to expect the new Iranian campaign—dubbed “Operation Epic Fury,” a name more fitting for a revenge plot than an unprovoked war of choice—to remain as low-cost or bloodless for the U.S. in personnel, equipment, or economic terms as Trump’s two previous one-off strikes, Operation Midnight Hammer and Operation Absolute Resolve. By Sunday morning, U.S. Central Command confirmed that three American service members had already been killed and five more wounded in the operation.
Part of Trump’s calculus for launching strikes now is the assumption that Iran, weaker than it has been in a generation, cannot mount a devastating response. It is true that Iran’s traditional network of proxy terror attacks has been weakened in recent years: Israel has dismantled much of Iran’s proxy infrastructure since October 7, including its high-profile pager attack targeting Hezbollah, and Trump’s 2020 assassination of Iranian general Qasem Soleimani eliminated the architect of Iran’s global terror operations.
Even so, few strategic analysts believe Iran has no ability to strike targets far beyond the Middle East. Intelligence officials have repeatedly warned that Iran is actively hunting the U.S. officials who oversaw the Soleimani strike. In a move rooted in petty presidential spite, Trump already withdrew the security details protecting three former officials targeted by Iran: ex-Secretary of State Mike Pompeo, Pompeo aide Brian Hook, and former national security adviser John Bolton.
Iran has a long track record as a major terror threat, a point Trump himself acknowledged in an unusual overnight address over the weekend—though he also spread false claims to bolster his case. He correctly noted that Iranian-backed groups bombed the U.S. Marine barracks in Beirut in the 1980s, and later helped kill and injure thousands of U.S. service members in Iraq. But he also incorrectly implied Iran was behind the 2000 bombing of the USS Cole, a claim rejected by extensive FBI and U.S. government investigations that confirm the attack was orchestrated by al Qaeda. He also shared misinformation claiming Iran interfered in both the 2020 and 2024 U.S. presidential elections.
The U.S. always holds the upper hand in the opening hours of a military campaign, when its unmatched intelligence and cutting-edge military technology deliver maximum advantage. But what will happen once Iran has time to organize a sustained response? Even Trump acknowledged this risk, admitting in his speech that “the lives of courageous American heroes may be lost.”
2. No clear definition of what victory entails
Trump first won the presidency in part by tapping into widespread public anger at the endless Forever Wars in Iraq and Afghanistan. He carried that anti-war messaging through the 2024 campaign: when JD Vance endorsed Trump in 2024, he penned an op-ed titled “Trump’s Best Foreign Policy? Not Starting Any Wars,” arguing Trump would break the pattern of 21st-century presidencies that dragged the U.S. into unnecessary conflict. “My entire adult lifetime,” Vance wrote, “has been shaped by presidents who threw America into unwise wars and failed to win them.”
After winning re-election, Trump declared in his victory speech: “I’m not going to start wars, I’m going to stop wars.” He has spent much of his second term campaigning for a Nobel Peace Prize, at one point settling for the entirely unrecognized FIFA Peace Prize. Even in this year’s State of the Union, the White House highlighted Trump’s supposed record of “Ending Wars and Fostering Peace.”
Yet this is the second time in as many months that Trump has launched a decapitation strike against a U.S. adversary with little to no apparent planning for what comes after. Venezuela, the target of the earlier raid, has already vanished from the news cycle almost as quickly as it arrived, and huge questions remain about the future of its leadership and ongoing U.S. involvement there.
After announcing Khamenei’s death on Truth Social, Trump wrote: “This is the single greatest chance for the Iranian people to take back their Country. We are hearing that many of their IRGC, Military, and other Security and Police Forces, no longer want to fight, and are looking for Immunity from us … Hopefully, the IRGC and Police will peacefully merge with the Iranian Patriots, and work together as a unit to bring back the Country to the Greatness it deserves.”
He promised bombing would “continue, uninterrupted throughout the week or, as long as necessary to achieve our objective of PEACE THROUGHOUT THE MIDDLE EAST AND, INDEED, THE WORLD!”
Even the famously thin post-invasion planning for the 2003 Iraq War—when the Bush administration toppled Saddam Hussein and Dick Cheney infamously claimed U.S. troops would be “greeted as liberators”—looks like a masterclass in strategic preparation compared to the complete lack of planning around Trump’s push for war with Iran. Trump never even made a formal case for military action to Congress, and the only clear goal coming out of the White House is the vague promise of “regime change,” rooted in the naive hope that a few well-placed bombs will be enough to spark a democratic transition in Iran.
Trump has pulled off high-profile, successful tactical strikes before, like the 2019 killing of ISIS leader Abu Bakr al-Baghdadi, and he appears to be betting that the American public does not care about long-term planning. Cycle after news cycle, he has proven that U.S. public attention spans are just as short as his own. It is even possible he does not have a clear vision of what victory in Iran looks like. As former national security adviser John Bolton told me last fall: “He doesn’t do grand strategy.”
“It is very hard for people to understand,” Bolton said. “It was very hard for me to understand, because you think in government that’s what it’s about—policy is what you do. That's not what Donald Trump does. Therefore, when people talk about a Trump doctrine in international affairs, it’s a complete fantasy to think that there’s any coherence to it at all.”
Much of the future of Iran and the Middle East hinges on what Trump considers a success, or when he loses interest and moves on to another issue. Trump has repeatedly ruled out deploying U.S. ground troops, and Vice President JD Vance told The Washington Post: “The idea that we’re going to be in a Middle Eastern war for years with no end in sight—there is no chance that will happen.” But the core question remains: how much change can the U.S. force on Iran’s regime from the air alone?
3. Conflicts of interest tied to Trump’s business empire
One of the biggest open questions is how Trump’s personal business ties to the Middle East shape his decision-making. The Trump family’s finances are notoriously opaque, but most analysts believe a large share of the family’s current wealth is tied to Gulf royal families. Since his first presidency, Trump and his family have built deep financial ties with multiple Gulf states: Saudi Crown Prince Mohammed bin Salman invested $2 billion in Jared Kushner’s private equity fund, Trump owns a branded golf course in Dubai, and a company backed by a UAE royal investor bought a 49% stake in Trump’s family cryptocurrency firm last year.
Qatar, which Trump labeled a “terror funder” in his first term, has also curried favor in his second term, most notably by donating a plane to use as Air Force One. Shortly after the donation, Trump offered Qatar an unprecedented U.S. security guarantee—an entirely coincidental development, per the White House.
All of these U.S.-aligned Gulf states and their ruling families are now under attack or at risk of Iranian missile, drone, and terror strikes. It is not a conspiracy theory to ask: as Trump weighs the path forward and decides when “enough is enough,” will he prioritize what is best for the United States, or the geopolitical and financial interests of his business partners? What will happen if Iranian strikes continue to hit civilian infrastructure in these countries? Over the weekend, Dubai International Airport—one of the world’s busiest travel hubs—was damaged in an Iranian strike. Trump has intermittently pledged to support Iranian pro-democracy protesters, but it is hard to imagine he will sustain a war effort that threatens his own personal business profits.
4. A long history of American misadventure in Iran
While modern American public memory tends to focus on the messy aftermath of the Iraq and Afghanistan wars, Iran has been a source of geopolitical and political trouble for U.S. presidents for far longer. Arguably, no other country has tripped up more American presidents over the past 80 years than Iran—even though it was once one of the United States’ closest economic and military partners in the region.
In 1953, President Dwight Eisenhower authorized the CIA-led Operation Ajax, a coup that deposed Iran’s democratically elected prime minister and installed Mohammad Reza Pahlavi as Shah. Pahlavi went on to rule Iran for decades, becoming one of the largest buyers of U.S. arms and a key regional anchor of stability for the United States.
But the arrangement eventually unraveled with catastrophic consequences for multiple U.S. presidencies. Richard Nixon saw his presidency roiled by oil crises orchestrated by the Shah; Gerald Ford’s efforts to manage the oil crisis set the stage for the Shah’s regime to collapse; and Jimmy Carter lost his re-election bid over the Iranian hostage crisis that followed the 1979 revolution that ousted the unpopular Shah.
Ronald Reagan won the presidency partly thanks to public anger over the hostage crisis, and evidence suggests his campaign secretly negotiated with Iran to delay the hostages’ release to boost his political chances. Reagan later spent much of the 1980s mired in the Iran-Contra scandal, an illegal arms-for-hostages deal with Iran. His administration also grappled with the fallout of the Iran-Iraq War, including the 1988 downing of Iran Air Flight 655 by the USS Vincennes that killed 290 Iranian civilians—an incident still seared into Iranian national memory, even if most Americans have forgotten it.
Today, most young Americans do not remember when Iran was second only to the Soviet Union as America’s top geopolitical foe. Throughout the 1980s, the U.S. fought a costly shadow war with Iran in the Persian Gulf. As historian David Crist documents in his definitive history The Twilight War, the U.S. Navy fought regular skirmishes with Iranian patrol boats, and Iranian mining and attacks on commercial shipping damaged or destroyed more than 500 ships during the Iran-Iraq War—an amount of lost tonnage equal to roughly half of all shipping lost to German U-boats during the Battle of the Atlantic.
The naval conflict was only one part of the confrontation with Iran’s post-revolutionary regime. In the 1980s and 1990s, Iran ordered the assassinations of at least 80 people around the world. U.S. officials also blame Iran for the 1996 bombing of Khobar Towers in Saudi Arabia that killed 19 American service members. The case became a major political flashpoint for the Clinton administration and the early George W. Bush presidency, when a young Justice Department prosecutor named Jim Comey led the indictment of 14 Iranian suspects just before the statute of limitations expired.
In the years after 9/11, Iran supplied explosive devices to Iraqi insurgents that killed and maimed thousands of U.S. troops. In 2006 and 2007, U.S. troops detained a dozen Iranian intelligence officers in Iraq, including Brigadier General Mohsen Chizari, head of Iran’s Iraq operations, charging them with targeting U.S. personnel.
More recently, Iran has become a capable adversary in cyberspace. While it does not match the sophistication of Russian or Chinese hacking groups, it is “good at finding ways to maximize the impact of their capabilities,” according to Jeff Greene, former executive assistant director for cybersecurity at the Cybersecurity and Infrastructure Security Agency (CISA). Iran was responsible for a series of high-profile distributed denial-of-service attacks on Wall Street institutions that rattled global financial markets in the 2010s, and its 2012 cyberattack on Saudi Aramco and Qatar’s Rasgas was one of the first major destructive cyberattacks on critical global energy infrastructure.
Today, Iran is almost certainly assessing which of these many tools, networks, and operatives it will deploy to retaliate. Given its long track record of terror and cyberattacks, there is no reason to assume Iran’s response will be limited to missile strikes in the Middle East alone.
5. No one can predict how this conflict will conclude
There is a famous (likely apocryphal) anecdote of a 1970s conversation between Henry Kissinger and a Chinese leader, variously identified as Mao Zedong or Zhou Enlai. When asked about the legacy of the French Revolution, the Chinese leader reportedly replied: “Too soon to tell.” The story may not be true, but it captures a critical truth about upheaval in a nation as old as the 2,500-year-old Persian Empire: history unfolds over generations, and its consequences are rarely visible in the moment.
While Trump and much of the world hope Iran will transition to democracy in the wake of Khamenei’s death, the CIA’s official February assessment concluded that Khamenei would likely be replaced by hard-line leaders from the Islamic Revolutionary Guard Corps (IRGC) if he was killed. So far, that assessment appears to hold: Iran has continued launching retaliatory strikes across the Middle East throughout the weekend, even after the reported deaths of multiple senior regime officials including Iran’s defense minister—directly contradicting the claim that the Iranian government is on the brink of collapse.
Modern Iranian history since World War II has been defined by three pivotal moments that intersect with American foreign policy: the 1953 CIA coup, the 1979 revolution that ousted the Shah, and now the 2026 U.S. airstrikes that killed the supreme leader. In his recent best-selling book King of Kings, which chronicles the fall of the Shah, veteran foreign correspondent Scott Anderson writes of the 1979 revolution: “If one were to make a list of that small handful of revolutions that spurred change on a truly global scale in the modern era, that caused a paradigm shift in the way the world works, to the American, French, and Russian Revolutions might be added the Iranian.”
It is impossible to ignore that we are now living through another moment of equally historic importance, one whose consequences we cannot yet begin to imagine. Given how far-reaching the aftershocks of past Iranian upheavals have been, we should be extremely wary of premature celebrations or declarations of victory.
Defense Secretary Pete Hegseth has repeatedly framed the Trump administration’s foreign policy with the vulgar acronym FAFO, short for “fuck around and find out,” meant to warn adversaries of the consequences of crossing the U.S. Today, the U.S. has done the first half of that mantra, launching war from the skies over Iran. The long, fraught history of American engagement with Iran
The Five Big Known Unknowns of Trump’s Iran War
