The Iran War is Likely to be another Trump Failure

What is it like to go to war while being led by someone with the intellect of a bowling ball? We are in the midst of finding out. For most of his life, cult leader, convicted felon, and failed President Donald Trump has followed a pattern of failing miserably at something, and then being bailed out by others, only to declare himself a success. The United States-Israel war against Iran is showing all the hallmarks of a traditional Trump endeavor. It has been marked by stupidity, failure, and, now, an effort to get others to rescue him from his self-created problems.

More than two weeks into the war, it is still not clear why Trump decided to start it. The stated objectives of the war change day-by-day, and no clear conditions for ending the war have been articulated. Based on recent media reports, Trump ignored the advice of experts, wrongly predicted a quick end to the war, and did not have a backup plan. As a result, he is now floundering.

The Wall Street Journal reports that Trump believed that the Iranian regime would likely capitulate after its leadership, including Supreme Leader Ali Khamenei, was killed. Similarly, the New York Times has an article saying:

In the days leading up to the war in late February, senior Israeli officials told Prime Minister Benjamin Netanyahu that if the initial strike against Iran succeeded in killing a large portion of the Iranian security establishment, including the supreme leader, there was a good chance that protests against the government would erupt again quickly.

The Times further says that "Mr. Netanyahu appeared to sell that idea to Mr. Trump". We now know that this expectation did not come to pass. There has been no popular uprising in Iran, and, according to Reuters, "U.S. intelligence indicates that Iran's leadership is still largely intact and is not at risk of collapse any time soon".

I lived in Kuwait for parts of 1987 and 1988. While I was there, Iran mined the Persian Gulf, attacked shipping, and fired Silkworm missiles at oil facilities, including an oil loading dock in Kuwaiti waters. The possibility of Iran closing the Strait of Hormuz was constantly discussed. Therefore, it would be astonishing that U.S. military planners would not expect that Iran might close the strait in response to an U.S. attack. The Wall Street Journal reports that this likelihood was, in fact, not overlooked, saying "Before the U.S. went to war, Gen. Dan Caine, the chairman of the Joint Chiefs of Staff, told President Trump that an American attack could prompt Iran to close the Strait of Hormuz." The Journal says that Trump acknowledged the risk, but expected that the Iranian regime would be defeated before closing the strait and, "even if Iran tried, the U.S. military could handle it." Senator Chris Murphy says that administration officials who briefed Senators revealed that they "had NO PLAN. I can't go into more detail about how Iran gums up the Strait, but suffice it to say, right now, they don't know how to get it safely back open."

These are two fundamental miscalculations by Trump: He wrongly expected the Iranian people to rise up after the regime was decapitated, and he did not expect the Strait of Hormuz to be closed. Moreover, he did not have backup plans in case these two assumptions were not met. There was no plan to reopen the Strait of Hormuz if it was closed. As we now know, both of Trump's assumptions were wrong, and now we are in a bit of a quagmire. Moreover, these were not the only errors made by Trump in the run-up to the war.

As Trump repeatedly demonstrates, he is both a buffoon and a bully. He is stupid enough to make frequent bad decisions and powerful enough to normally force others to submit to his will. There is a story going around now that Trump has purchased shoes that don't fit for nearly his entire cabinet. As a result, grown men, many of them millionaires or even billionaires, are walking around in shoes that are several sizes too large rather than risk his wrath by not wearing them. This is the sort of obsequiousness that Trump expects. Back in February 2025, Trump held a heated meeting with Ukrainian President Volodymyr Zelenskyy. Both Trump and Vice President and reply guy JD Vance berated Zelenskyy, with Vance criticizing Zelenskyy for not saying "thank you”. But a very important part of the meeting came when Zelenskyy warned Trump that "During the war, everybody has problems, even you. But you have nice ocean and don't feel now, but you will feel it in the future." Trump reacted angrily and told Zelenskyy, "You don't have the cards right now."

As it turns out, Zelenskyy did have a card and still has it. Moreover, as he predicted, Trump has a problem and needs help from Ukraine. During Russia's war with Ukraine, Iran has supplied Russia with Shahed drones. As the saying goes, necessity is the mother of invention. Out of necessity, Ukraine developed low-cost anti-drone weapons and the expertise to use them. In fact, according to Axios, in a White House meeting in August, Zelenskyy offered to sell their battle-proven technology for destroying Iranian-made drones to the United States. According to the article, "The Trump administration dismissed the Ukrainians". As soon as the war started, Iran began firing missiles and launching drones at targets in Israel and the Gulf states. Missile defense systems were highly effective against missiles, but Iran had success with its drones. Not only have seven members of the U.S. military been killed in drone attacks, but billions of dollars of equipment has been destroyed by the inexpensive aircraft. Suddenly, the U.S. needs Ukraine's anti-drone weapons.

Trump still does not have enough functioning brain cells to understand that the calculus has changed. When asked about Zelenskyy's offer to help with anti-drone technology this weekend, Trump responded by saying, “We don’t need help" and that the "last person we need help from is Zelenskyy." Perhaps without Trump's knowledge, U.S. officials had already approached Ukraine to seek assistance, and the Ukrainians had already sent interceptor drones to protect U.S. bases in Jordan.

As I wrote last week, Trump and his administration have struggled to outline the objectives of the war. Regime change has been on and off the agenda. Similarly, ending Iran's nuclear ambitions is sometimes cited as a goal and sometimes not. But it is rapidly becoming clear that opening the Strait of Hormuz to traffic is emerging as the dominant goal of the war, even if it is not explicitly stated as such. As a result of the strait's closure, oil prices have surged from less than $60 a barrel to nearly $100 a barrel and sometimes more. Moreover, the strait's closure is causing problems that can't easily be reversed. As oil storage facilities reach capacity, oil producers are shutting down wells. It takes time, perhaps months, to restart such wells. In addition, the longer the strait remains closed, the higher oil prices will rise. No surprise then that over the past few days, Trump has repeatedly focused on reopening the Strait of Hormuz.

Again, the saga of the Strait of Hormuz is textbook Trump. Initially, he did not expect it to be closed. Therefore, he did not plan for its closure. Once it was closed, he acted like it wasn't a problem. Even last week after several oil tankers had been attacked and set on fire, Trump told reporters that "The straits are in great shape. We’ve knocked out all of their boats. They have some missiles, but not very many. I think we’re in very good … we’re in very good shape." This was delusional and completely contrary to what was obvious to anyone paying attention. As I said above, when Trump finally realizes that he had blundered, he turns to others to bail him out. That was his task over the weekend.

Trump has spent most of his second term attempting to weaken NATO and alienating European leaders. Even after the war started, he kept up his belligerence. For instance, Trump claimed that the United Kingdom Prime Minister Kier Starmer offered to send two aircraft carriers to the Gulf. Trump's claim was false. The UK only has two aircraft carriers, and one is currently out of action. Nevertheless, Trump "truthed" on Truth Social "That’s OK, Prime Minister Starmer, we don’t need them any longer — But we will remember. We don’t need people that join Wars after we’ve already won!" Now, all of a sudden, Trump is calling on the Europeans to help reopen the Strait of Hormuz. In multiple statements over the weekend, Trump argued that other countries depend on oil from the Persian Gulf more than the United States does and, therefore, they should have a role in defending Gulf shipping from Iran.

Trump clearly still does not understand the complexities presented by Iran's closure of the Strait of Hormuz. It is not an easy problem to solve. Trump has repeatedly threatened Iran. For instance, writing on Truth Social that "If Iran does anything that stops the flow of Oil within the Strait of Hormuz, they will be hit by the United States of America TWENTY TIMES HARDER than they have been hit thus far." So far, Trump's threats have had no impact. Now that Trump has kicked a hornet's nest, the Europeans are not interested in getting involved. Finland's navy responded by saying, "Finland's three mine clearance vessels are designed for Finnish conditions and cannot be deployed outside the Baltic Sea." Germany's defense minister asked, "What does Trump expect from a handful of European frigates that the powerful U.S. Navy cannot do? This is not our war, we have not started it." Reinforcing this point, Germany's Chancellor Friedrich Merz said, "We will not participate in securing the Strait of Hormuz and we do not know a concept for doing so." Trump is now in the process of brow beating European leaders in order to get them to participate.

What is clear is that Trump's arrogance and stupidity caused him to ignore the advice of experts, even when he sought such advice, which was rare, and instead rely on his own instincts and the advice of those such as Netanyahu and Trump's son-in-law Jared Kushner. Trump still does not seem to understand Iran's strategy and makes the classic error of believing that overwhelming force is sufficient to win a war. Trump should learn more about the concept of asymmetrical warfare. Iran's goal is not to defeat the U.S. militarily, but rather to bleed it sufficiently that Trump decides that the war is no longer worth it. The primary means for this is economic pressure resulting from stopping the flow of oil from the Persian Gulf. Closing the Strait of Hormuz is key to that strategy. Even if Trump succeeds in cobbling together some sort of international flotilla, that is unlikely to be sufficient to significantly change the current status quo. As long as Iran has a will to keep the strait closed, the country will likely find a way. We are led by a mad king, and this is where he has led us.