President Donald Trump holds up a fist after disembarking Air Force One at Palm Beach International Airport in West Palm Beach, Florida, February 27, 2026. (AP/Matt Rourke)

Before strikes, Trump was told attacking Iran is high risk, high reward

As US president pushes for regime change, CIA estimates that assassination of Khamenei won’t necessarily topple the Islamic Republic

by · The Times of Israel

Ahead of Saturday’s US-Israel attack on Iran, US President Donald Trump received briefings both warning of the potential major US casualties and touting the prospect of a significant shift in the Middle East in favor of US interests, a US official told Reuters Saturday.

The official, who spoke on condition of anonymity, said the briefers described the operation to the president as a high-risk, high-reward scenario.

The launch of the major joint strike on Iran on Saturday morning plunged the Middle East into a new and unpredictable conflict. The US and Israeli militaries struck sites across Iran, triggering retaliatory attacks against Israel and nearby Gulf Arab countries.

The briefings from Trump’s national security team hint at what propelled Trump’s decision to pursue arguably the riskiest US military operation since the invasion of Iraq in 2003.

Ahead of the strikes, Trump received multiple briefings from officials, including CIA Director John Ratcliffe, US General Dan Caine, the chairman of the Joint Chiefs of Staff, US Secretary of State Marco Rubio and Defense Secretary Pete Hegseth.

On Thursday, Admiral Brad Cooper, who leads US forces in the Middle East as the head of Central Command, flew to Washington to join discussions in the White House Situation Room.

A second US official said that prior to the strikes, the White House had been briefed on a number of risks associated with operations against Iran, including the possibility of retaliatory strikes on US bases in the region that could overwhelm defenses, as well as Iranian proxies attacking US troops in Iraq and Syria.

Smoke rises from an area in the direction of Al Udeid Air Base, which houses the Qatar Emiri Air Force and foreign forces, including the US, in Doha on February 28, 2026, following a reported Iranian strike. (Photo by MAHMUD HAMS / AFP)

Trump and Prime Minister Benjamin Netanyahu have indicated that the goal of the current offensive is to topple the Islamic Republic, with both world leaders calling on the Iranian people to seize the opportunity and take over their government.

Strikes targeted Supreme Leader Ali Khamenei and President Masoud Pezeshkian, an Israeli official said, but the results of the attacks were not yet clear. Several senior Iranian Revolutionary Guards Corps (IRGC) commanders and political officials were killed, an Iranian source close to the establishment told Reuters.

Even if US and Israeli forces were to eliminate Khamenei, CIA assessments indicated that he would likely be replaced by hardline figures from the IRGC, two sources briefed on the intelligence said.

The assessments produced over the past two weeks looked broadly at what could occur in Iran following a US intervention and the extent to which a military operation could trigger regime change in the Islamic Republic — now a pronounced objective for Washington.

The intelligence agency reports did not conclude any scenario with certainty, said the sources, who spoke on condition of anonymity to discuss intelligence matters. The CIA declined to comment.

This handout picture provided by the office of Iran’s Supreme Leader Ayatollah Ali Khamenei shows him during an address in Tehran on February 17, 2026. (Office of the Iranian Supreme Leader via AP)

In an early morning video address on Saturday, Trump described Tehran as a “terrorist regime” and encouraged the Iranian people to take over the government, saying the US military strikes would set the stage for an uprising.

The US and Israeli assault came after weeks of deliberation inside the US government about whether to strike Iran following the deadly protests that broke out there in December, which were followed by a series of renewed nuclear talks.

These negotiations were supposed to continue on Thursday. Washington and Tehran ostensibly agreed on the date, but in retrospect, it appears this was an act of misdirection by the Americans.

In a briefing last week, Secretary of State Marco Rubio told top congressional lawmakers known as the Gang of Eight that a US operation would likely move forward, but that Trump could change his mind, particularly if nuclear negotiations were successful. Those talks in Geneva did not result in an agreement.

Rubio notified the Gang of Eight on Friday night that the operation to attack Iran was likely to commence in the following hours, but said Trump could still change his mind, two sources familiar with the matter said.

After the strikes began, Iran vowed a crushing response and launched repeated missile barrages at Israel starting at around 10 a.m., sending millions into shelters repeatedly as air defenses worked to intercept the threats. As of 8 p.m., at least 40 missiles had been launched at Israel, but there were no reports of direct impacts in residential areas.

The Magen David Adom ambulance service said it treated a total of 89 people who were lightly injured as a result of Iran’s missile attacks, the vast majority of them indirectly.

Times of Israel staff contributed to this report.