Pentagon officials' heated debates foreshadowed problems in Iran

As Houthi militants in Yemen attacked ships with missiles and drones in the Red Sea early last year, top U.S. officials gathered at the Pentagon to prepare military options for President Donald Trump. Their meetings repeatedly grew tense.

On one side were Gen. Michael “Erik” Kurilla, then overseeing U.S. operations in the Middle East, and other hawks ready for action. The general was keen on military action not only against the Houthis but also against Iran, which had backed the Yemeni paramilitary group for years with weapons and training, according to people familiar with the matter. Like others, they spoke on the condition of anonymity to discuss internal government deliberations.

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On the other side were officials hesitant to launch military strikes so early in the second Trump administration, including the Joint Chiefs chairman, Gen. Charles Q. Brown Jr., who suggested that new U.S. assessments of what military action might yield would be wise before presenting the president with military options.

That triggered an abrupt response from Kurilla, people familiar with the matter said.

“General,” Kurilla said, “the time for assessments is over.”

The exchange, which has not previously been reported, surprised some in the room. Defense Secretary Pete Hegseth, then new to his role, agreed with Kurilla, people familiar with the matter said.

The disagreement came as other Pentagon appointees, including then-senior adviser Dan Caldwell and policy official Alex Velez-Green, repeatedly raised questions in meetings about how an extended military campaign against the Houthis could deplete stocks of key U.S. munitions, the people familiar with the discussions said. That issue has since grown in prominence as the Trump administration burned through its arsenal of cruise missiles and interceptors in a war with Iran that is now seven months old.

In recent weeks, the Iranian-backed Houthi militants have launched a new offensive in Yemen, seizing control of the strategically important Bab al-Mandab Strait, reigniting civil war and targeting critical energy infrastructure in Saudi Arabia. On Sunday, Yemen’s Saudi-backed government announced a military campaign to take back all land seized by the Houthis, who retaliated with a new wave of strikes against Saudi Arabia’s main oil company, Aramco. With Iran’s proxies weakened elsewhere, the group has emerged as the most powerful element of Tehran’s “Axis of Resistance” against the United States and Israel.

In March 2025, weeks after the disagreement between the generals, Trump announced Operation Rough Rider, a 51-day bombing campaign against the Houthis that almost immediately was embroiled in scandal when then-White House national security adviser Mike Waltz accidentally invited a reporter into a group chat on Signal, the unclassified messaging application.

More than 1,000 targets were hit over the course of Rough Rider, including key Houthi commanders and weapons stocks. But the aerial bombing also resulted in significant civilian casualties, human rights groups said.

Trump and Hegseth touted the campaign as a resounding success, but other senior Pentagon officials, including Caldwell and Joe Kasper, Hegseth’s first chief of staff, questioned whether the campaign had clear and obtainable objectives, the people familiar with deliberations said.

The U.S. went on to strike Iran’s nuclear facilities in Operation Midnight Hammer in June 2025 and, along with Israel, launched a sprawling war against Iran this February.

A spokesperson for Hegseth, Kingsley Wilson, said in a statement that Rough Rider “achieved decisive success against Houthi forces,” with U.S. forces launching strikes that “severely degraded radar networks, air-defense systems, ballistic-missile and drone launch sites, weapons depots, and production facilities while removing multiple mid- and senior-level commanders from the battlefield.”

The military action, Wilson added, “substantially reduced immediate threats to vital international shipping lanes, compelled a clear tactical shift by the adversary, and helped create conditions for a ceasefire that strengthened freedom of navigation in the region.”

She declined to comment on the possibility of any future action in Yemen, but she said the Pentagon’s role is to “develop and present military options to the President, and he makes the final choice.”

The White House and the Pentagon both released statements defending the management of weapons stockpiles after The Washington Post shared its reporting that some administration officials had concerns about it before Rough Rider began. U.S. officials have said that while the U.S. military has a deep arsenal of weapons, it is increasingly running low on specific munitions, such as ship-launched Tomahawk cruise missiles and Patriot air-defense interceptors.

“The United States Military has enough munitions and ammo to serve all of the Commander-in-Chief’s strategic goals and beyond,” White House spokeswoman Anna Kelly wrote in a statement.

Kasper and Caldwell declined to comment, while Velez-Green could not be reached for comment.

Kurilla, who retired in August 2025, did not respond to requests for comment about the exchange with Brown or the objectives of Rough Rider.

Brown declined to comment through a spokesperson, but a person familiar with his thinking said he did not dispute the account of the testy Pentagon deliberations. It’s common, that person said, for a top commander to push for quick military action while the Joint Chiefs chairman considers a wider range of issues, including making sure all necessary plans and requirements are in place and that the president’s options are preserved.

Brown was fired and forced into retirement just before Rough Rider, as Hegseth pushed to remove top Biden-era generals. An official with Hegseth’s office declined to say whether Brown’s caution about the Houthis played a role, saying that “out of respect for our senior military leaders,” they do not discuss “the nature of their retirements.”

An abrupt ceasefire

The military campaign in Yemen abruptly ended in May 2025 with a ceasefire brokered by Oman. Trump claimed victory and said that the Houthis “don’t want to fight anymore.”

“They gave us their word that they wouldn’t be shooting at ships anymore, and we honor that,” Trump said.

The end of combat operations, officials and analysts said, came after the Houthis showed remarkable resiliency in the face of American airpower. No U.S. troops were killed during the operation, but the militants shot down at least seven MQ-9 Reaper drones, and U.S. forces lost two F/A-18 fighter jets in mishaps at sea. The operation, people familiar with the effort said, was followed by the administration’s near-total abandonment of Yemen.

“It was like … a cord being pulled out of a socket,” said a former U.S. official who worked on Yemen issues at the time. Trump “wanted to scratch Yemen off the list and move on.”

When the mission was declared over, the former official said, some in U.S. Central Command, which Kurilla then oversaw, were “apoplectic,” believing that they had been making progress. A U.S. special envoy position for Yemen issues was never filled by the Trump administration, and Washington’s assistance to the impoverished country was slashed.

At the time, the former official said, they warned colleagues: “You ignore Yemen at your own peril.”

‘Folkloric status’

The disagreements at the Pentagon about how to proceed on Yemen underscore the competing views in the U.S. government about how to handle the persistent threat the Houthis have posed since they seized power in northern Yemen in 2014.

The Shiite militia, which formed in the 1990s, aims to control Yemen, a country of 35 million at the southwest tip of the Arabian Peninsula. From 2015 to 2022, the Houthis, with support from Iran, fought a bloody civil war against Yemen’s internationally recognized government, which is backed by Saudi Arabia.

That war ended with a fragile truce that left the Houthis holding large swaths of the country’s north and the government coalition in control of the south.

But the group has much larger ambitions, including ousting the U.S. from the Middle East and destroying the state of Israel.

April Longley Alley, a senior fellow at the Washington Institute, said that Houthis “see themselves as the tip of the spear in the Arab world.”

Dan Shapiro, who served as U.S. ambassador to Israel during the Obama administration, described the Houthis as “an enduring problem” for decades to come.

“We’re kind of stuck with this bad actor on this maritime choke point, able to activate and try to use their position or leverage at the moment of their choosing,” said Shapiro, who later became a Pentagon official during the Biden administration.

After the Hamas attacks on Oct. 7, 2023, the Houthis started firing missiles at Israel in retaliation for the resulting military campaign in Gaza.

That is when the Houthis took on an almost “folkloric status,” said Tim Lenderking, the U.S. envoy to Yemen during the Biden administration.

“It really bolstered their standing and their brand in the Arab world,” he added.

But the Houthis took it too far, he said, firing on U.S. and Israeli ships, killing international mariners and disrupting the flow of commercial traffic in the Red Sea.

The Biden administration launched military strikes against the Houthis beginning in January 2024. The Houthis appeared undeterred.

Trump launched Rough Rider on March 15, 2025. A few days later, he declared that “tremendous damage” had been inflicted on the “Houthi barbarians” and would get worse.

“It’s not even a fair fight, and never will be,” Trump wrote in a social media post. “They will be completely annihilated!”

Unclear objectives, mounting costs

The costs and questions quickly mounted. Over the course of the operation, estimated at more than $1 billion, the Houthis continued to target U.S. warships in the Red Sea and surrounding waterways.

U.S. forces struck a migrant detention center in Yemen in April 2025, reportedly killing more than 68 civilians and injuring dozens more, according to Human Rights Watch.

The operation also was dogged by the “Signalgate” scandal, in which senior Trump administration officials, including Hegseth and Vice President JD Vance, communicated about Rough Rider in a group chat that accidentally included Atlantic journalist Jeffrey Goldberg.

The revelation was especially damaging for Hegseth, who had shared specific, advance details about how the bombing would begin through the unclassified Signal app. A review by the Pentagon inspector general released in December found that Hegseth’s actions “created a risk to operational security,” though the secretary of defense and his team claimed “total exoneration.”

The Trump administration began looking for an exit from Rough Rider just a couple of weeks into the bombing campaign, said Alley of the Washington Institute. There had been an assumption going into the campaign that “you could go in and coerce the Houthis with overwhelming power to change [their] behavior.”

But Trump lacked a clear exit strategy, Alley said, so when Oman - long a mediator in the region - approached the administration saying that the Houthis wanted a truce, Trump took it.

One of the people familiar with internal deliberations at the Pentagon said that the abrupt end to Rough Rider bolstered the belief among internal critics that the offensive’s objectives were never clear in the first place.

“It almost seemed,” this person said, “that Trump had buyer’s remorse.”

The deal, Trump said at the time, was simple: The Houthis would stop firing at U.S. ships if the U.S. stopped firing at the Houthis.

“We hit them very hard and they had a great ability to withstand punishment,” Trump said in announcing the ceasefire. “You could say there was a lot of bravery there.”

‘They rebuilt it all’

Yemen’s Saudi-backed coalition government was supportive of Rough Rider and caught off guard when it ended, according to a Yemeni official, who spoke on the condition of anonymity because of the sensitivity of the situation.

“The Trump administration did not read the situation strategically,” said the official. “They just wanted a quick win.”

It was not long, the person said, before the Houthis “rebuilt everything.”

In recent weeks, the Houthis have repeatedly attacked oil infrastructure and military bases in Saudi Arabia, which also saw its key East-West oil pipeline attacked by Iraqi militias.

As Saudi Arabia - long a key U.S. ally - faces its biggest threats in years, it has confronted Trump’s unwillingness to get more involved and looked to new partners for help in confronting the Houthis. Saudi Arabia and its allies in Yemen’s government fought on Monday to take back land along Yemen’s western coast to regain control of Bab al-Mandab, in a counteroffensive that analysts said could substantially deepen the conflict.

Nadwa Al-Dawsari, a Yemeni researcher and conflict analyst, said the Trump administration never should have seen the truce as a win.

“The Houthis have learned how to use negotiations, ceasefires and truces as a tactic to preserve their power, rebuild their capabilities and prepare for the next round of conflict,” she said.

Houthi spokesperson Mohammed Abdulsalam said that Rough Rider “sparked widespread resentment regarding the U.S.” and led to an influx of volunteers.

Yemen, he said in a written statement to The Post, is known as the “graveyard of invaders.”

“Anyone who has attempted to colonize or occupy the country,” he said, “has left burdened by woes, sorrow, failure, and defeat.”

Trump struck a conciliatory tone in recent weeks when talking about the Houthis, saying last month in Ireland that the Houthis “called us, and they don’t want to fight us.”

“Everything will work out very well,” he said.

The Yemeni official said that they fear the Trump administration still does not understand the threat that the Houthis pose, noting that the group is already working extensively with al-Shabab in Somalia and has clearly stated intentions to push the U.S. out of the region and destroy the state of Israel.

“The lesson I learned over the past 10 years is to take the Houthis seriously,” the official added. “I am not sure if the United States learned the same lesson.”

Alley said that Trump’s decision last year to forge a truce with the Houthis had the unintended consequence of showing the militant group the limits of Trump’s willingness to escalate - giving them additional room to maneuver.

“Trump may be done with the Houthis,” she said, “but the Houthis are not done with Trump.”

Susannah George contributed to this report.

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This article originally appeared on Washington Post at https://washingtonpost.com/world/2026/10/05/pentagon-dispute-trumps-first-war-foreshadowed-iran-challenges/