Trump squeezes Iran with maximum pressure — why it hasn’t forced a breakthrough

After two months of conflict, neither a deadly bombing campaign nor a blockade on Iranian exports has forced Tehran to make the concessions the Trump administration is seeking.

The campaign has intensified in recent weeks, targeting Iran’s oil exports and financial networks while a naval blockade has disrupted shipments through the Strait of Hormuz, a critical artery for global energy flows. U.S. officials argue the combination of military pressure and economic isolation is intended to weaken Iran’s capabilities and force it back to the negotiating table on more favorable terms.

While the U.S. has killed Iran’s Supreme Leader Ali Khamenei and dozens of top military and political figures, the regime itself remains intact. His son, Mojtaba Khamenei, was selected to succeed him, and leadership remains firmly hardline.

Aaron David Miller, a former State Department Middle East negotiator and fellow at the Carnegie Endowment, said the administration may have misjudged the type of negotiating partner it would face.

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"Trump was looking for an Iranian Delcy Rodriguez," he told Fox News Digital. "More likely, he's going to end up with an Iranian Kim Jong Un."

He expressed doubt that any decisive victory was possible while the current Iranian regime remained in power.

"And we do not have the capacity to remove the regime."

The standoff increasingly has become a test of whether U.S. pressure can be converted into political concessions — or whether it is instead being diluted through workarounds, institutional resilience and competing constraints.

So far, analysts say, Iran has proven more capable of absorbing and rerouting pressure than Washington has been able to translate it into durable gains.

On Monday, Iran floated a proposal to reopen the Strait of Hormuz in exchange for relief from the blockade, while deferring negotiations on more contentious issues.

But analysts caution that such proposals do not address the core dispute and may not even mean the same thing to both sides.

"What the Iranians mean by opening the straits, and what Trump means, may be two different sorts of things," Miller said.

At the center of the standoff is Iran’s nuclear program, where the gap between the two sides remains wide. The Trump administration has pushed for Iran to eliminate its uranium enrichment capability entirely, while Iran insists that enrichment is a sovereign right and non-negotiable — leaving little room for compromise.

That divide continues to block a broader agreement, even as both sides explore more limited steps to reduce immediate tensions.

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"It’s almost unimaginable that this administration and the Iranian leadership are willing to make the kinds of concessions that would allow this administration to walk away with a win," Miller said.

"Iranians are willing to give concessions, but Trump is looking for capitulation," said Trita Parsi, executive vice president of the Quincy Institute for Responsible Statecraft think tank. "And you can't get a country to capitulate unless you have defeated them."

Instead of folding under pressure, Iran largely has responded by adapting. 

Despite the blockade, Iran has continued to move at least some oil through workaround methods, including sanctioned vessels, smaller ports and alternative routing strategies, even as overall exports have come under strain.

Those efforts have expanded in recent weeks. Reports indicate Iran is exploring overland shipments, including potential rail exports to China, while vessels have increasingly rerouted through Iranian territorial waters or controlled shipping corridors to bypass restrictions.

"The United States successfully closes off one avenue for them, and slowly but surely they are finding workarounds," Parsi said.

The financial impact of the campaign has been significant, even if uneven. Estimates vary, but some analysts put Iran’s potential losses from the blockade at roughly $400 million per day, largely driven by disrupted oil exports and reduced access to hard currency.

At the same time, Iran has not been fully cut off. The country has continued to generate billions in oil revenue in recent months, underscoring both the scale of the pressure and its limits.

While a sustained drop in oil revenue would strain the government’s official budget and force cuts to public spending, the country’s most powerful institution, the Islamic Revolutionary Guard Corps, operates through its own economic networks, including smuggling routes and cross-border trade.

That allows key parts of the regime to continue functioning even under heavy sanctions, meaning economic pain often falls unevenly — hitting civilians before it weakens the state’s coercive apparatus.

Even attempts to directly destabilize Iran’s leadership have not fundamentally altered that dynamic. U.S. and Israeli operations earlier in the conflict killed Khamenei along with dozens of senior military and political figures.

Yet the regime has remained intact, with power consolidating among remaining political and security elites aligned with hardline positions.

How long Iran can sustain that posture remains uncertain. Miller said a prolonged blockade could eventually force a breaking point — but only if Washington is willing to maintain it.

"If the administration is prepared for six months to keep up this blockade, I think they could probably break the Iranian economy," Miller said.

But he cautioned that such timelines are difficult to predict and that even U.S. intelligence lacks a clear picture of when economic pressure might translate into political concessions.

That uncertainty raises a broader question about the sustainability of the strategy. While Iran’s leadership may be willing to absorb significant economic pain, the U.S. faces its own constraints, including potential strain on military resources and growing risks to global energy markets.

"There are no midterms. There are no primaries. There are no sell-by dates for Iran," Miller said. "And Trump has a sell-by date."

The White House did not respond to a request for comment. 

For now, both sides appear to be waiting for the other to lose the political will to sustain the standoff, with global energy markets caught in the middle.