Can We Lose the Same War Twice? With Trump, Anything’s Possible

The first phase of Donald Trump’s war on Iran ended in defeat and humiliation. Iran emerged battered but stronger, with two new weapons: control of the Strait of Hormuz and a demonstrated drone and missile force that can cripple the economies of its Persian Gulf neighbors and wreak havoc on U.S. bases. Both are new instruments of power more usable than nuclear weapons.

The two New Jersey property managers Trump sent to negotiate his surrender produced a poorly written memorandum of understanding, or MOU, that captured the new power relations—Iran got nearly everything it demanded, including a $300 billion reconstruction fund, while the United States got vague promises of talks on all the issues Trump had started the war to resolve.

In particular, point five of the MOU, which seems dictated by Iran and accepted by the hapless Steve Witkoff and Jared Kushner, clearly gave Iran authority over all traffic through the strait: “Iran will make arrangements using its best efforts for the safe passage of commercial vessels with no charge for 60 days only.”

So why did Trump restart the war? As Maggie Haberman and Jonathan Swan write in their new book, Regime Change, “Unlike recent Presidents, Trump had shown he was entirely comfortable using extraordinary presidential powers on a whim.”

Those extraordinary powers include the ability to launch waves of destructive attacks solely on his order. But these attacks, now numbering hundreds of sorties, are pointless. If it were possible to bomb Iran into submission, it would have worked the first time.

Trump has been stewing over his loss. He accomplished none of the objectives he repeatedly promised, including:

Overthrowing the Iranian regime. The government is likely stronger than before the war and certainly more hard-line.

Obliterating Iran’s nuclear program. Trump and Israel failed last July to destroy the program and failed again this year. Though it is damaged, Iran retains significant quantities of enriched uranium and can rebuild its production facilities.

Destroying Iran’s missile fleet. Iran retained 70 percent of its missile capabilities after the war, according to U.S. intelligence, and is rebuilding the rest. Its drone fleet is also intact and perhaps more capable than its missiles.

Ending support for regional militias. A key goal for Israel, Iran’s network of regional militants is substantially weaker, but much of this happened before the war (Israel’s post–October 7 decapitation of Hezbollah, notably), and in any case, Iran shows no sign of ending its support for Hamas, Hezbollah, and others.

Destroying Iran’s navy. Much of Iran’s surface fleet was destroyed, but hundreds of fast patrol boats remain capable of executing their main mission: interdicting shipping through the strait.

Demonstrating U.S. power and resolve. The U.S. has lost credibility regionally and globally and weakened its alliances, the greatest source of U.S. global power. Persian Gulf states are reassessing the U.S. bases built on their territory since the 1991 Iraq War. Once seen as security assets, they now appear to be a security liability.

As with his 2020 election loss, Trump now seeks to bend reality. He didn’t lose the war, he claims, he won it. He achieved all his objectives, he says. In an absurd social media post Monday, Trump claimed that the Strait of Hormuz is “OPEN, and will remain OPEN, with or without Iran.”

He told Fox News, “We are going to keep the strait. We will probably run it. We’ll become the guardian of the strait. Maybe we’ll call it the ‘guardian angel’ of the strait.” He announced that he would charge a 20 percent fee on all cargo shipped (a claim he retracted on Tuesday).

In so doing, Trump not only demonstrated the severe state of his delusions but undermined his own administration’s repeated assertions that, as Marco Rubio said, “No country is allowed to charge tolls or fees on an international waterway.”

He is now also violating international law. Long before the Law of the Sea Treaty guaranteed free passage through international waters, the United States fought a war against those we called the Barbary Pirates (off “the shores of Tripoli”) to uphold the right of unhindered shipping.

Trump’s boasts also helped legitimize Iran’s position on charging its own fees. Iran, which has been excellent at trolling Trump, immediately posted back. Iranian Foreign Minister Abbas Araghchi tweeted, “POTUS is absolutely right. Whoever provides secure and safe passage of commercial vessels through the Strait of Hormuz should be compensated for this service.” He mocked Trump’s weird capitalization, saying that “Iran has always been the GUARDIAN of the Strait and will remain so FOREVER. 20% is of course too much. We will be fair.”

Trump’s claim that the strait is open is an obvious lie. On Sunday, only 14 ships transited the strait, one-tenth the prewar volume. There is no way the U.S. Navy, even if it were to triple the number of ships deployed, could keep the strait open. One drone hitting one tanker can send insurance rates so high as to make transit prohibitively expensive.

Before Trump’s new attacks over the past week, the strait was slowly getting back to prewar traffic. But it was all through Iranian waters, under Iranian authority.

Iran directed all ships to transit through the Iranian side of the strait. Trump, as he does domestically, then tried to assert an authority he does not have. The U.S., working with Oman, sent ships through routes along the Omani side, promising to protect them. It could not. Iran, claiming this was a violation, struck the ships (which is also a violation of the MOU pledge not use force or threats of force). The U.S. struck back at Iran; Iran launched attacks on U.S. bases in Kuwait, Jordan, Oman, and other nations; the U.S. struck again, and a new cycle of war was launched.

So, where will this go? With two volatile, fanatical, authoritarian regimes involved, it is difficult to predict. My best guess, in order of probability, is one of three scenarios:

The fighting will peter out after a few weeks. There is no viable military strategy for Trump. There is no way to actually force open the strait and keep it safe. Omani and Pakistani mediators are working to bring the two sides back to the table. They could work out a compromise, likely largely along Iranian terms.

We enter a new forever war. The current round of strikes ends, but there is no peace agreement. Traffic resumes but at low levels. Fighting flares up and dissipates in repeated cycles.

Violent escalation. One side causes damage so severe that the other side responds with even greater violence. Iranian strikes on U.S. bases could kill scores of troops. U.S. strikes on Kharg Island could severely damage Iran’s main oil terminal. These or many other possibilities could trigger a larger war than either side desired.

Democratic Representative Adam Smith of Washington, the ranking Democrat on the House Armed Services Committee, rightly called out Trump’s new folly. “I wholeheartedly condemn the president’s suggestion that the United States is going to take over the Strait of Hormuz,” he wrote to his colleagues on Monday. “There is likely no scenario in which the U.S. could take total control of the Strait of Hormuz without significantly escalating the conflict. It is past time for [Republicans] to work with us to ensure the president finds a diplomatic solution to ending a war he never should have started.”

We have to hope sufficient pressure builds to do just that. ...