How a U.S. General Won Trump’s Trust Through the Iran Airstrike Operation

With his sharp military expertise and no-nonsense approach, General Dan Caine quickly earned President Trump’s full confidence by flawlessly executing the recent airstrike campaign against Iran’s nuclear facilities.

When President Donald Trump and his top advisers began discussing a potential military strike on Iran earlier this month, Vice President J.D. Vance and Secretary of State Marco Rubio were focused on one thing: avoiding another drawn-out conflict in the Middle East. General Dan Caine, newly appointed Chairman of the Joint Chiefs of Staff, shared that concern.

Inside the White House Situation Room, Caine laid out a tactical map, detailing how the Pentagon could protect U.S. pilots and military personnel in the region from retaliation if the President ordered a strike.

Caine’s confidence and precision made a strong impression on Trump. When the strike on June 21 unfolded almost exactly as he had outlined—targeting three major Iranian nuclear sites—Trump’s trust in him only deepened.

Within a week of the operation, Caine had already addressed the public twice and received glowing praise from the President.

“General ‘Razin’ Caine is extraordinary,” Trump told reporters on June 25, using the general’s Air Force callsign—an indication of their close rapport.

Sources within the Pentagon say Caine has quickly become one of the President’s most trusted military advisers. In the days before and after the operation, he was a constant presence at the White House. During the strike itself, conducted under strict secrecy, Trump turned repeatedly to Caine for real-time updates and explanations.

“Caine is all about the details,” Vice President Vance told the Wall Street Journal. “In just two months, he’s overseen a precision air campaign that crippled Iran’s nuclear capabilities without a single American casualty. That’s the kind of leadership we need.”

But Caine now faces a delicate balancing act: maintaining his standing as a key adviser to President Trump without compromising the traditional nonpartisan role of the Joint Chiefs Chairman.

Trump’s history with military leadership is complicated. His relationship with former Chairman Gen. Mark Milley soured during his first term, with Trump even suggesting online that Milley should be executed. President Biden later issued a preemptive pardon for Milley in one of his final acts before leaving office, fearing legal retaliation under a second Trump administration.

At a Pentagon briefing on June 26, Caine avoided political rhetoric entirely. While Defense Secretary Pete Hegseth opened the press conference by praising Trump and criticizing the media for allegedly downplaying the operation’s success, Caine focused strictly on technical briefings—explaining the bunker-buster bombs used and outlining damage assessments at the targeted facilities.

Asked by a reporter whether he felt political pressure to alter his analysis, Caine didn’t hesitate. “No. I never have, and I never will,” he said.

Caine’s rise has been swift. A retired Air National Guard F-16 pilot, he spent much of his career in the Middle East and held covert roles with the CIA and U.S. Special Operations Command. He returned to service in 2024 after Trump’s reelection and was confirmed by the Senate in April with a 60-25 vote—making him the first retired officer and first non–four-star general to lead the Joint Chiefs.

His connection with Trump dates back to a 2018 visit to a base in western Iraq, where Caine briefed the President on counter-ISIS operations. According to insiders, Trump was struck by Caine’s direct style and tactical clarity.

“I remember the President saying something like, ‘Finally, someone who knows what they’re talking about,’” a former senior officer recalled.

Still, Caine has worked hard to dispel accusations of political favoritism. In his confirmation hearing, he refuted Trump’s claim that he once wore a MAGA hat and pledged to “kill for the President.” Caine testified under oath that he never made such a statement and never wore political gear in uniform.

Trump’s former National Security Adviser John Bolton backed Caine’s version, calling him “the model of a nonpolitical military officer.”

As the lead planner behind the “Night Hammer” operation, Caine laid out multiple options for the President, helped maintain operational secrecy, and coordinated post-strike damage assessments. Pentagon insiders say his clear communication and willingness to listen have made him an essential asset in Trump’s national security circle.

“He cuts through the noise,” one White House official said. “That’s why the President listens to him.”

At a post-strike Pentagon briefing, Caine, dressed in his Air Force blues, presented a measured summary. He confirmed that Iran’s nuclear sites had suffered “extensive and crippling damage,” but emphasized that a final assessment would take more time.

Notably, he made no mention of the President.

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