President Donald Trump is waiting for Iran to cave to his economic pressure. Tehran may be willing to wait even longer.

Even as Treasury Secretary Scott Bessent promises a level of economic isolation “never seen before,” former Trump administration officials, U.S. ambassadors and other Middle East experts are skeptical that tightening the economic vise will force Iran to relinquish its desire to toll ships passing through the State of Hormuz and make the other concessions Trump is demanding to bring an end to the war.

“It’s an attrition campaign, and I am sure Treasury tweaks this or that to fill gaps or expand coverage of sanctions,” said James Jeffrey, a former ambassador who served in the Middle East during three presidential administrations, including Trump’s first term. “But, it’s hard to believe [there will be] something decisive after 20 years of U.S. sanctions and Iranian experience of going around them.”

It’s an acknowledgement that underscores the asymmetry of the situation. The Trump administration is staring down a consequential midterm election amid an unpopular war that has sent oil prices back up to roughly $90 a barrel and helped push long-term borrowing costs to their highest level in nearly two decades as hope dims that a peace deal is near.

Iran’s leaders, meanwhile, see the conflict as existential, giving Tehran reason to absorb the extraordinary economic pain rather than accept terms it believes could imperil the regime — especially as U.S. inflation remains elevated and treasuries sell off.

The yield on 30-year U.S. government bonds, a figure Trump has in the past been attuned to, jumped on Tuesday to its highest level since just before the global financial crisis.

The increase in the yield to its highest level in nearly two decades isn’t solely because of the six-month war; global fuel shortages and broader instability have kept energy prices higher for longer, increasing the threat of persistent inflation. And that’s heaped even more risk on global bond markets that have repeatedly blanched at Trump-related shocks.

“We are in a situation where we’re spending more and more to finance more and more,” said Julia Coronado, founder of MacroPolicy Perspectives. And the war has created “a riskier world full of more frictions, full of more supply shocks.”

Iran’s outsized incentive to muscle through the pain is partly why some former administration officials doubt that the naval blockade, while unprecedented in its scale in the modern era or whatever new strategies Bessent may unveil, will change Iran’s calculus.

“I think the economic pressure would need to hit them in new ways we haven’t seen so far to change the mindset of the regime,” said one former Trump administration official, granted anonymity to candidly assess the impact of the U.S.’s economic pressure campaign.

The administration has yet to indicate what further action it plans to take, but options include going after major Chinese banks that facilitate Iran’s oil trade, expand secondary sanctions on countries doing business with Iran and confiscating Iranian assets under U.S. jurisdiction instead of just freezing them.

Iranian leaders publicly mocked U.S. efforts to sanction them into submission.

“Americans think squeezing Iran harder will win concessions that were never part of the agreement,” Mohammad Bagher Ghalibaf, the speaker of Iran’s parliament, posted on X Tuesday.

“Bessent and [Defense Secretary Pete] Hegseth are way out of their league,” he wrote. “Stop waiting for the clown crew to pull a rabbit out of their hat and clean up the mess you made.”

White House aides, however, continue to contend that the leverage is on its side.

“The crushing sanctions and one of the most successful blockades that have crippled Iran’s economy and has left Iran completely broke,” said one administration official, granted anonymity to share the U.S.’s thinking. “There are many levers the president can crank harder in the weeks and months ahead.”

In the half-year since the Iran war began, the president has deployed an array of pressure tactics to choke Iran economically, including physically preventing the country from selling its most important export — oil — as part of an ongoing naval blockade of Iranian ports. The administration has also sanctioned foreign buyers of Iranian oil, targeted the country’s shadow fleet of ships that ferries it and sought to cut the country off from the financial networks it uses to move money.

That economic pressure has sent Iran’s economy, which was already troubled before the war, into a deeper tailspin. Now, Iran is grappling with year-over-year inflation of 88 percent, long lines and rationing at gas pumps and food prices that have more than doubled.

But those who have worked on previous Iran negotiations say that’s far from enough to get the regime to cave, especially after six months of U.S. bombing that has killed, by Tehran’s own measure, more than 3,000 Iranians.

“It’s undeniable that there is economic pressure. The question is whether there is a breaking point, and I would say for a regime that is fighting for its life and has never hesitated to transfer economic pain to its population, there is no breaking point,” said Ali Vaez, the International Crisis Group’s Iran project director, who helped work to bridge differences between Iran and world powers during negotiations over the 2015 nuclear agreement.

Yet Trump continued to project patience on Tuesday, signaling that he was prepared to let the pressure campaign play out.

“There are no talks or conversations going on, or scheduled, with the Islamic Republic of Iran. The Naval Blockade remains in full force and effect. The Hormuz Strait is open and operating. All water mines have been removed or detonated. Thank you for your attention to this matter!” Trump wrote on Truth Social.

A senior White House official, granted anonymity to discuss the situation in Iran, insisted that Iran will cave long before the pain in the U.S. or world markets become intolerable.

“Ultimately we want a deal, but in the interim, the Iranian economy is tanking … people are lining up for gas, just for a half gallon of gas. And there’s a lot of civil unrest going on in Iran, that’s not being played on the news for whatever reason,” the official said late last week. “We’re fine if that’s the route they want to take.”

Still, there are signs inside the White House that the economic impacts are a growing concern. Vice President JD Vance last week said on Fox News that the administration’s first goal in the Iran war was to “keep oil and gas cheap for Americans all over the country.” The president, meanwhile, has repeatedly insisted voters will bear the pain of higher gas prices for an end to Iran’s nuclear ambitions.

The voters have a more dyspeptic view. A Reuters/Ipsos survey released this week showed Trump’s approval rating at 33 percent, the lowest level of his presidency. Roughly 80 percent of Americans — 87 percent of Democrats and 71 percent of Republicans — think U.S. involvement in Iran “will go on for an extended period of time,” the poll found.

But some former Trump administration officials, however, are holding out hope that patience will be rewarded and that the administration’s economic pressure campaign will work, in part because they see the other options on the table, including putting U.S. boots on the ground in Iran, as politically untenable.

Fred Fleitz, Trump’s former National Security Council chief of staff and vice chair of the American First Policy Institute’s American Security, predicted that the U.S. could be “dealing with a different Iran” in 30 to 60 days.

“I think patience is the best approach,” Fleitz said. “I don’t believe that a large-scale military attack right now is going to make a difference in changing the regime’s position, and I strongly oppose the idea of seizing Kharg Island or sending in American troops. The American people don’t want that. That would really bog us down in a quagmire.”

NEW YORK — Wall Street executives spent three years doing everything they could to distance themselves from former President Donald Trump. Now they’re busy coming up with reasons to vote for the guy.

Many high-dollar donors at banks, hedge funds and other financial firms had turned their backs on Trump as he spun unfounded claims that the 2020 election had been stolen and savaged the judicial system with attacks. Today, they’re setting aside those concerns, looking past qualms about his personality and willingness to bulldoze institutional norms and focusing instead on issues closer to the heart: how he might ease regulations, cut their taxes or flex U.S. power on the global stage.

“I don’t know that anyone really believed he was a threat to democracy,” said Point Bridge Capital founder Hal Lambert, an investor and Republican donor. Lambert had backed Florida Gov. Ron DeSantis in the 2024 primary but is now supporting Trump.

Republican business titans from hedge fund executive Nelson Peltz to hotel mogul Robert Bigelow have come out in favor of the presumptive GOP nominee. Even those who loudly denounced Trump's efforts to overturn the results of the 2020 election are backing his bid to return to the White House.

Blackstone Group CEO Stephen Schwarzman — who once labeled the U.S. Capitol insurrection that followed a Trump speech on Jan. 6, 2021, “an affront to the democratic values” of the country — is once again one of the former president’s most important allies on Wall Street. Top financiers like hedge fund billionaire Bill Ackman, who called on the then-president to resign over the riot, and Citadel’s Ken Griffin, who dubbed Trump a “three-time loser” in elections, are considering offering their support.

The new embrace of Trump threatens to further blunt the fundraising edge that President Joe Biden maintained through the opening innings of the 2024 campaign. But beyond that, it suggests that a key Biden argument — that Trump’s actions since his 2020 defeat have made him unfit to lead the country again — is falling flat with a pivotal constituency that has an especially large stake in the rule of law.

The former president "is a much better choice than what we have now. Just check out the four years that Trump was in office versus the three years that President Biden was in office,” said John Catsimatidis, the billionaire New York radio station owner and real estate investor. Gas and food prices were lower. It was easier to conduct business, he said, and it was a lot cheaper to secure financing for second homes.

“I remember I got a mortgage on one of my homes I bought in the suburbs for 2.75 percent,” said Catsimatidis, who is estimated by Forbes to be worth $4.3 billion. “It's horrible what's going on."

Though he’s a longtime Trump ally, Catsimatidis is no longer an outlier among the Republican Party’s top donors. Trump will have a major opportunity to persuade even more corporate leaders to support him when he speaks to the nation’s top CEOs at the Business Roundtable’s quarterly meeting on June 13. Biden will be traveling to Italy for the G7 meetings, so White House chief of staff Jeff Zients will address the Roundtable in his stead.

“Donald Trump is a self-obsessed convicted felon who would do anything to regain power — and if he does, has made clear he intends to rule as a dictator on day one,” Biden campaign spokesperson Ammar Moussa said. “But for some billionaires none of that matters. They’ll prop up a convicted white-collar crook so long as Trump slashes their taxes.”

Corporate America’s dismay at Trump’s behavior around Jan. 6 has faded — even after his recent criminal conviction for falsifying business records about payments made to porn star Stormy Daniels. What’s more, Wall Street firms and Silicon Valley venture capitalists have grown increasingly antagonistic toward Biden as appointees like Federal Trade Commission Chair Lina Khan and Securities and Exchange Commission Chair Gary Gensler move to tighten rules around markets and mergers.

Kathy Wylde, president and CEO of the Partnership for New York City, a nonprofit organization that represents the city’s top business leaders, said Republicans have told her that “the threat to capitalism from the Democrats is more concerning than the threat to democracy from Trump.”

Democrats hoped that Republican donors in the financial services world would remain on the sidelines in 2024, fatigued by Trump’s conspiracy theories and bellicose public persona. Many of the high-profile contributors now lining up behind him had flocked to candidates like DeSantis or former U.N. Ambassador Nikki Haley, who they believed would offer the benefits of Trump’s business-friendly agenda without the baggage.

As Trump cleared the field, GOP donors grew increasingly skeptical about Democratic claims that a second term for the former president would spell doom for democracy.

“It seems you’re at the end of the anti-Trump arguments if that’s the argument you have to make,” said Key Square Group founder and major Trump donor Scott Bessent, a former chief investment officer at Soros Fund Management.

Lambert said that for a lot of Republican donors, Jan. 6 and its aftermath was a lot like the leaked Access Hollywood tape that many thought would doom Trump’s 2016 campaign.

“They assumed this was the end of his political support in this country. Which has happened time, and time, and time again,” he said.

Biden and his allies still consider Trump vulnerable on his legal challenges, 2020 conspiracy theorizing and relentless attacks on the justice system. The president recently told donors at a fundraiser in Greenwich, Connecticut, that Trump’s claims of a rigged justice system were “reckless and dangerous.”

A recent ABC/Ipsos poll found that a majority of Americans view Trump’s guilty verdict in New York as “correct,” though its overall impact on the presidential race is marginal. The latest New York Times/Siena poll found that his lead over Biden shrank following the conviction.

Still, many Republican donors have rejected Biden’s warnings about the dangers of a second Trump term. Instead, they claim Trump’s conviction in New York, along with the cases brought by special counsel Jack Smith and Georgia prosecutors, were politically motivated and damaged the rule of law.

Eric Levine, a longtime GOP fundraiser and former Treasury official who had said he would never vote for Trump after the Jan. 6 riot, told POLITICO that the criminal cases brought against the former president were a factor in why he changed his mind.

Shaun Maguire, a partner at Sequoia Capital and former Hillary Clinton supporter, pledged $300,000 to pro-Trump efforts minutes after the verdict. His examination of the charges Trump faced had been a “radicalizing experience,” he wrote on X, formerly known as Twitter.

The Trump campaign says it hauled in $141 million last month, with nearly 38 percent arriving after the May 30 verdict.

“Donors big and small are coming to the table to support President Trump because they realize Joe Biden is weak and dishonest, and America cannot afford four more years of his failed policies,” Trump campaign press secretary Karoline Leavitt said in a statement.

Spokespeople for Schwarzman, Ackman and Griffin declined comment. Peltz and Bigelow did not respond to requests for comment.

Ben Lefebvre contributed to this report.