More than six months ago, on Feb. 28, President Donald Trump ended a speech announcing U.S. and Israeli strikes on Iran with a stirring message to the Iranian people.

“To the great, proud people of Iran, I say tonight that the hour of your freedom is at hand,” Trump declared. “When we are finished, take over your government. It will be yours to take.”

Hours later, Israeli Prime Minister Benjamin Netanyahu issued a similar message: “Citizens of Iran: Persians, Kurds, Azeris, Abkhazians and Baluchis,” he said. “This is your time to join forces, topple the regime and secure your future.”

With those words, Trump and Netanyahu went public with a high-stakes gamble. The two leaders hoped to spark an uprising by the Iranian people that would topple Iran’s hard-line theocratic regime. 

In a best-case scenario for Trump and Netanyahu, Iran’s new leaders would normalize relations with the outside world, abandon the country’s nuclear program and end its support of terrorist proxies. In many ways, a successful uprising was the surest and swiftest way for the U.S. and Israel to achieve their primary war objectives.

But the Iranian government was not overthrown.

And now the Trump administration finds itself locked in a protracted conflict with Iran — with no clear exit.

Six current and former U.S. officials granted anonymity to describe sensitive intelligence matters told MS NOW that erratic messaging from Trump and a lack of rigorous planning hampered efforts by Trump and Netanyahu to ignite an uprising inside Iran — just as they have hampered the broader U.S. war effort.

They called the failed attempt to encourage a rebellion in Iran six months ago “rushed,” “amateurish,” “not realistic,” “flawed from the beginning” and “a fantasy.”

“While I fully support this administration’s decision to finally take action against the Islamic Republic of Iran,” Glenn Corn, a former senior CIA official and professor at the Institute of World Politics, told MS NOW, “I think the White House’s messaging on the objectives has been undisciplined and all over the place.”

The failure also appeared to spark recriminations between U.S. and Israeli officials this summer. A senior Israeli official obliquely blamed the U.S. for the unsuccessful effort during Netanyahu’s July visit to the White House.

When an MS NOW reporter asked why the Israeli intelligence given to Trump before the war on the likelihood of regime change succeeding appeared to be incorrect, the senior Israeli official said Netanyahu did not promise Trump that the Mossad could easily spark an uprising.

Instead, the official said, Netanyahu was “very careful” to phrase that an attack “could advance the probability or the possibility” that an uprising would succeed.

Netanyahu told Trump “that if we are able to do certain things, we have a chance of creating conditions where the Iranian people could take their fate into their own hands,” the senior Israeli official told reporters. 

“Several of these conditions did not materialize,” the senior official added, “not for lack of insight, but for either operational failure or decisions that were made.”

Anna Kelly, a White House spokesperson, said Trump has achieved his goals in Iran.

“From the outset, President Trump was clear about his goals for Operation Epic Fury: destroy Iran’s ballistic missiles, dismantle their production facilities, sink their navy and weaken their proxies,” she said. “The United States Military met or exceeded all of its objectives. Now, Operation Economic Outcast, combined with the most successful military blockade in history, are crippling Iran’s economy and making them more isolated than ever before.”

The CIA declined to comment. The government of Israel and its intelligence agency, Mossad, did not respond to MS NOW’s requests for comment.

Current and former U.S. officials say the plan was rushed and overly optimistic. Success depended on achieving multiple complex actions inside and outside Iran.

An Iranian government internet blackout that prevented protesters from communicating with one another would have to be breached. Iran’s divided opposition groups needed to unify, and elements of Iran’s regular army would need to support the opposition. And in one scenario, Iranian Kurds armed by the U.S. would attack Iran from Iraq.

John Bolton, a longtime Iran hawk who served as one of Trump’s first-term national security advisers and pleaded guilty in June to willfully retaining national defense information, said achieving such goals requires months of intensive preparation.

“The planning for an uprising suffered from the same problem as the planning for the war, which was virtually no planning at all,” Bolton told MS NOW. “The idea of arming the Kurds and then they march into Tehran and topple the regime is a fantasy.”

Mixed messages

The war began with a spectacular intelligence breakthrough. U.S. intelligence agencies reportedly determined that Iran’s Supreme Leader Ali Khamenei was meeting with dozens of other senior leaders in a compound in Tehran.

Israeli forces bombed the compound, killing Khamenei and dozens of other senior officials and commanders. Days later, reports of a potential ground invasion of Iran by Kurdish groups began to circulate.

On March 4, five days into the war, White House press secretary Karoline Leavitt said at a press briefing that reports Trump had agreed to any plan for the Kurds to launch an insurgency in Iran were “completely false.”

The next day, Trump said in an interview with Reuters that he thought an assault by Iranian Kurds based in Iraq would be “wonderful.”

Two days later, he reversed himself. “We are not looking to the Kurds going in,” he told reporters aboard Air Force One. “I’ve ruled that out.” He later accused Kurdish forces of stealing the weapons the U.S. had given them, saying in a Fox News radio interview, “The Kurds took the guns.”

Turkish President Recep Tayyip Erdogan urged Trump not to arm the Kurds, as he has done repeatedly in the past, citing the threat Kurdish separatists pose to his government, the British newspaper The Telegraph reported last month.

Iranian leaders, meanwhile, moved to block a Kurdish attack. Iranian forces and their allies conducted 388 missile and drone attacks against Kurdish forces in Iraq in the first month of the war, Reuters reported.

The Islamic Revolutionary Guard Corps also moved forces into northeastern Iran, a heavily Kurdish area, apparently to discourage an uprising there.

Ted Singer, a former senior CIA official who oversaw the agency’s operations in the Middle East, said U.S. and Israeli officials should have expected the Iranian regime to respond. He cited a famed 19th-century Prussian military adage.

“No plan survives first contact with the enemy,” Singer told MS NOW.

On March 13, Trump appeared to back away from his call for Iranian protesters to take over their government during a Fox News radio interview. He said plainclothes militia aligned with the hard-line IRGC would likely gun down demonstrators.

Trump predicted protests would begin but probably “not immediately.”

He also said protests were “a big hurdle to climb for people that don’t have weapons,” referring to opponents of the Iranian government. “They literally have people in the streets with machine guns, machine-gunning people down if they want to protest. OK?” he said.

Trump had accurately described ways Iran’s security forces had confronted widespread protests inside the country a month before the U.S. and Israel attacked the country.

Widespread protests across Iran in January were confronted by the Iranian government with machine guns and sniper rifles, according to analysis by BBC News Persian. Thousands of protesters died.

‘Rise up and fight’

After the initial attempt to encourage a revolt failed, the Trump administration backed away from making public comments pushing for regime change.

In recent weeks, however, Trump and Treasury Secretary Scott Bessent revived the call for an Iranian uprising.

“To the ordinary soldiers supporting this regime, as more and more of your paychecks stop or are supposedly just delayed, ask whether your commanders are leading your country to triumph or to ruin,” Bessent said Aug. 24 when announcing a new aggressive sanctions campaign to cripple Iran’s economy. “And recall that the Berlin Wall fell when ordinary soldiers decided not to shoot at their own people.”

On Sept. 1, Trump mused in a Truth Social post, “When are the Iranian people going to rise up and fight?”

Trump’s failure to end the tit-for-tat cycle of military action also reduces the chance of widespread protests, said Iran expert Behnam Ben Taleblu, the senior director of the Iran program at the Foundation for Defense of Democracies.

“So long as the fog of war is there in a meaningful way, it will be hard to get nationwide anti-regime protests,” said Taleblu.

While the one-two punch of a U.S. maritime blockade of Iran and increased sanctions could eventually spark a mass revolt, Taleblu cautioned that hoping the next protest will take care of the current regime is “fundamentally wishful thinking.”

“We have to be a little bit more humble about what it is that the street can achieve, he added.”

Taleblu predicts the sanctions will be successful but questions whether Washington will be ready to meaningfully support protesters by getting weapons into the country, engaging with the opposition and restoring internet service in Iran.

“Unfortunately, I don’t see the U.S. having done that because these are hard, politically precarious, costly and not an immediate return on investment,” he said, referring to aggressively supporting the protesters. “The longer the delay, the greater the cost, and the less likelihood the success.”

Corn said he still supports the U.S. war with Iran and credits Trump with aggressively confronting a regime that has targeted Americans for decades. But he said it would take time to defeat it. 

“I would assess that those who believed in a ‘quick win’ were not realistic,” he said. “The Islamic Republic had been sinking its roots into Iran and the regime for decades. It was unrealistic to think that a quick air war would defeat that regime.”

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