Iran’s Plan for Trump’s Midterms: Pain at the Pumps

Sep 25, 2026 02:19 PM EDT, Fri

‘Pain for Trump’: Iran is trying to escalate the war before the midterms

Trump’s actions look increasingly indecisive as Tehran focuses on driving up oil prices.

By David Rohde and Felicia Schwartz

Sept. 22, 2026, 5:00 AM EDT

President Donald Trump has hesitated in recent days to expand the war against Iran, even as Iranian-backed proxies in Yemen have driven up oil prices by escalating attacks against Saudi Arabia and threatening tanker traffic in the Red Sea.

At the same time, Iran’s strategy is becoming increasingly clear: find new ways to disrupt the international oil supply before the midterm elections to create a political pain point for Trump.

But that hasn’t convinced Trump to take action.

When Saudi officials asked Trump to join Saudi attacks on Iran-backed Houthi militia in Eastern Yemen, Trump declined, according to a person familiar with the phone call who was granted anonymity to describe the sensitive conversation.

For now, Trump is committed to maintaining a unilateral ceasefire with the Houthis, though the group knows Washington’s “red lines,” said a U.S. official who was granted anonymity to discuss sensitive diplomacy.

Ted Singer, a former senior CIA official who oversaw the agency’s operations in the Middle East, said the Iranian regime’s goal is to maximize the political damage to Trump.

Singer said Iran’s focus between now and November is singular: “pain for Trump.”

Tehran is clearly suffering economically from a U.S. blockade that has halted Iranian oil exports, said Singer, who served in seven countries across the Middle East. But they are gambling that Trump will be weakened by the results of the midterms, he said, and the Democrats — if they take control of Congress — could pass a war powers resolution limiting Trump’s military options.

The Iranian government is probably hurting themselves economically, Singer said, but “they are betting that bad election results will bring more pressure on Trump.”

Singer said that Trump’s threat this weekend to “blow the entire nation up” with air strikes will not necessarily topple the Iranian regime. He said the deployment of U.S. ground troops inside Iran or an uprising by Iranians are needed to achieve that goal.

“Maybe after the midterms, he’s willing to put boots on the ground,” Singer said.

Iranian President Masoud Pezeshkian is expected to arrive at the U.N. General Assembly shortly after Trump returns to [ Washington.

The Trump administration took the unusual step to grant visas to Pezeshkian and other senior Iranian officials even though Washington and Tehran have been fighting a war for more than six months.

While a meeting between the two leaders is unlikely, in an interview with Faux News on Sunday, Trump said he is “open” to meeting Pezeshkian. There are currently no plans for Trump to meet the Iranian president, said a U.S. official who was granted anonymity to describe Trump’s schedule.

Qatar and Pakistan are continuing to try to mediate an end to the fighting, with the U.S. and Iran submitting proposals over the weekend in response to a fresh push to resume diplomatic talks, said a Middle East diplomat who was granted anonymity to describe the closed-door negotiations.

Trump came close to meeting an Iranian president at the United Nations in 2019, when tensions were high following his decision to withdraw from the Iranian nuclear deal and wage a “maximum pressure” sanctions campaign against Tehran, according to two former Trump administration officials.

“Iran will be a central topic” for Trump and other members of the U.S. delegation, said a senior U.S. official who was granted anonymity to discuss the administration’s thinking.

Gregory Brew, a senior Iran and oil analyst at the Eurasia Group told MS NOW that it’s clear Trump’s decision-making over how far to go against Iran has waffled.

“Trump has nothing but bad options, and as a result, he’s become more indecisive,’ Brew said.

“Escalation would do little to address his growing economic and political problems, while Iran and its allies have shown they are tough to intimidate — and have potent tools to retaliate,” he said.

Brew said Iran’s negotiating position is unchanged. Iran is asking Trump to agree to the lapsed June memorandum of understanding that established a ceasefire. Iran also wants the U.S. to recognize Iran’s claims that it controls the Strait of Hormuz, a power it did not have before Trump chose to attack Iran seven months ago.

The Trump administration has rejected those terms.

“Having launched this war in February,” Brew said, “he seems to have no clear idea of how to escape it.”

David Rohde is the senior national security reporter for MS NOW and a two-time winner of the Pulitzer Prizes for International Reporting. Previously he was the senior executive editor for national security and law for NBC News.

Felicia Schwartz is a national security reporter for MS NOW.

Related Posts

Navigation Within