Caught between military escalation and renewed calls for negotiations, US President Donald Trump now finds himself facing a confrontation with Iran unlike any challenge of his second term. What was expected to be a swift campaign has evolved into a prolonged crisis shaped by military, political and economic complexities.
According to a report by The New York Times, written by White House correspondent Peter Baker, Trump has spent much of his second presidency compelling other countries to comply with US demands through political and economic pressure. Iran, however, has proven to be a very different challenge. The report argues that the administration has so far failed to develop a strategy capable of extracting concessions from Tehran, while the ceasefire agreement previously brokered by Washington has collapsed.
A Rapid Shift in Strategy
On the 136th day of the war, Trump announced a proposal to impose fees on ships passing through the Strait of Hormuz in exchange for US protection against potential Iranian threats.
Just one day later, however, he abandoned the proposal and introduced a different approach that no longer included transit fees. The New York Times described the abrupt reversal as further evidence of the administration’s lack of a consistent strategy for managing the crisis.
The newspaper reported that Trump’s retreat followed objections from Gulf allies, who showed little enthusiasm for bearing the financial burden of the proposed fees. It added that an operation initially expected to last between four and six weeks had now entered its twentieth week, forcing the US president to confront the reality that improvisation and sudden policy shifts were ineffective in a conflict of such complexity.
Iran Resists Trump’s Pressure Tactics
The report argues that Trump, who has made demonstrations of American power a defining feature of his foreign policy since returning to the White House, has encountered an adversary unwilling to respond to his usual methods of pressure.
Unlike previous disputes, where threats, tariffs or aggressive messaging on social media produced results, Iran has not altered its position in response to such tactics.
The New York Times also argued that the ceasefire announced last month amounted to little more than a “memorandum of misunderstanding”, failing to establish a meaningful foundation for negotiations. According to the report, this exposed the absence of a coherent political and military strategy for the next phase of the conflict.
Experts Say Tehran Is Playing by Different Rules
The newspaper quoted Vali Nasr, Professor of Advanced International Studies at Johns Hopkins University and adviser to several US presidents and secretaries of state on Middle East affairs, as saying Trump was facing a country that does not operate according to his usual political assumptions.
Nasr argued that Iran is not prepared to offer concessions simply to satisfy or accommodate Washington, but instead seeks to maximise its gains from any agreement it enters.
The report also noted that the current crisis serves as another reminder of the difficulty of achieving lasting political breakthroughs in the Middle East, a region that has repeatedly tested the ambitions of successive American presidents.
It added that instruments of power that have worked elsewhere in the world do not necessarily produce the same outcomes in the Middle East, a reality that has confronted numerous US administrations.
Confidence Meets Reality
According to The New York Times, this situation has been particularly frustrating for Trump, who has enjoyed a series of political victories since returning to office and has even described himself as potentially “the strongest man in the history of the world.”
However, the newspaper argued that persuading NATO members to increase defence spending, securing concessions from trade partners, or successfully conducting a military operation in Venezuela does not necessarily translate into the ability to dictate outcomes in the Iranian file.
Susan Maloney, Vice President of the Brookings Institution and Director of its Foreign Policy Programme, told the newspaper that Trump’s assertive approach had often benefited from favourable circumstances and from the willingness of other governments to seek compromise.
Iran, however, has shown no indication over several decades that it would respond in the same way.
Faulty Assumptions Behind the War
The report also cited John Hannah, former national security adviser to former US Vice President Dick Cheney and a researcher at the Jewish Institute for National Security of America, who argued that Trump overestimated Washington’s ability to bring down the Iranian government while underestimating its capacity to withstand sustained pressure.
According to Hannah, the war was built on flawed assumptions from the outset. He described the most serious error as Trump’s apparent belief that the Iranian government was a “house of cards” that could be toppled through air strikes or media escalation on social media platforms.
Hannah added that the problem extended beyond poor judgement, arguing that the United States also lacked a strong national security establishment capable of critically assessing presidential assumptions through professional analysis informed by foreign policy, defence and intelligence expertise.
A Temporary Ceasefire That Failed
The New York Times stated that the ceasefire agreement, which later collapsed as overnight air strikes resumed, was never a comprehensive peace agreement. Instead, it was intended as a temporary arrangement that would provide both sides with sixty days to negotiate more difficult issues, particularly the future of Iran’s nuclear programme.
The newspaper argued that the collapse of the arrangement raises serious doubts about the prospects for a lasting settlement, as any final agreement would require significant concessions from both parties, something that currently appears unlikely.
Military Pressure and Uncertain Diplomacy
According to the report, Trump remains uncertain about his next move.
While he has resumed military pressure through the renewed naval blockade of the Strait of Hormuz and has threatened to target the heavily fortified “Mount Pickaxe” site near one of Iran’s key nuclear facilities, he has shown little indication of returning to the extensive bombing campaign that characterised the early stages of the war, particularly as domestic opposition within the United States continues to grow.
At the same time, Trump continues to speak about the possibility of returning to negotiations, although he has offered no clear explanation of how talks that previously failed could now succeed. The newspaper interpreted his recent comments, in which he questioned the prospects of successful negotiations, as an attempt to lower expectations.
The report added that Trump believes mounting economic pressure will eventually force Tehran to make concessions, while Iran is betting that growing domestic pressure on the US administration, combined with rising energy prices and the approaching midterm elections, will work in its favour.
Concerns Over Political Consequences
Aaron David Miller, a former US negotiator on Middle East affairs and now a senior fellow at the Carnegie Endowment for International Peace, told the newspaper that Trump now finds himself confronting an adversary determined to preserve its strategic objectives, particularly maintaining influence over the Strait of Hormuz and strengthening its position in the Gulf.
Miller warned that just as the Iranian hostage crisis left a lasting mark on Jimmy Carter’s presidency, the current conflict could also shape Trump’s political legacy if it continues.
However, The New York Times noted that not all foreign policy experts share that assessment.
Former Republican official Elliott Abrams, who served in several Republican administrations including Trump’s first administration, argued that Iran is unlikely to derail Trump’s broader domestic and foreign policy agenda.
Abrams maintained that most Americans would not regard the conflict as a major priority unless it resulted in American casualties, while issues involving China, Ukraine and Cuba would remain politically separate from the Iranian crisis.
He also suggested that divisions within the Democratic Party over Israel and Palestine could ultimately become a greater electoral challenge for Democrats than for Republicans.
Hormuz Decision Highlights Internal Confusion
The newspaper argued that Trump’s rapid reversal over imposing fees on shipping through the Strait of Hormuz exposed growing confusion within the administration.
Trump had initially proposed a 20 percent fee on goods transiting the strait, arguing it would finance protection for international shipping. The report noted that the proposal contradicted previous US government positions, which had regarded such charges as inconsistent with international law.
His decision to abandon the proposal following discussions with Gulf leaders raised questions about whether those governments had been consulted before the announcement or whether their objections had simply been overlooked.
Trump later justified the reversal by saying Gulf states had instead promised substantial investments and trade agreements with the United States, although he provided no details regarding the scale or nature of those commitments.
Speaking to reporters, Trump said those countries would make significant investments in the United States and that he preferred this outcome over imposing fees, despite having described the proposal as “a matter of fairness” only one day earlier.
Contradictory Messaging on Iran
According to The New York Times, the policy reversal over Hormuz was not the only inconsistency in Trump’s recent approach.
The report noted that shortly after the ceasefire announcement, Trump praised Iranian negotiators as rational, intelligent people who were pleasant to deal with.
Only weeks later, however, he described them as “scum” and “sick people led by sick people.”
When asked about the dramatic shift in his position, Trump responded simply: “I got to know them.”
The newspaper suggested that the remark itself raised questions about how well he understood the counterparts with whom he had been negotiating.
No Clear Strategy
The report concluded by citing Abbas Milani, Director of the Iranian Studies Programme at Stanford University and a researcher at the Hoover Institution, who said he does not believe the United States has a coherent strategy towards Iran.
According to Milani, Trump is approaching the issue instinctively while attempting to pursue two contradictory objectives simultaneously: advocating for an agreement that would allow Iran’s economy to prosper, while at the same time threatening to destroy Iran and its civilisation.
