In the days leading up to the June 21 US airstrikes on Iran’s nuclear facilities, US President Donald Trump’s most trusted voice in the Situation Room wasn’t a longtime political aide or Cabinet official—it was General Dan Caine. Just months into his new role as chairman of the Joint Chiefs of Staff, Caine laid out a path for the strike that promised precision, minimal risk to American forces, and maximum impact. When the plan unfolded almost exactly as he had predicted, it solidified his place as one of Trump’s most influential military advisors, the Wall Street Journal reported.
Caine, a retired Air Force general brought back from civilian life to take on the Pentagon’s top job, had already impressed Trump during a 2018 trip to Iraq. But his calm authority and detailed presentations during the tense lead-up to the Iran strike elevated his status dramatically. In the days that followed, Trump praised him by his old Air Force nickname—“Razin’ Caine”—and leaned on him heavily in public and private as tensions escalated with Tehran.
From backroom briefings to battlefield execution
As US Vice President JD Vance and US Secretary of State Marco Rubio urged caution about being drawn into another long war in the Middle East, Caine offered Trump a middle path: a precise, hard-hitting operation that would avoid a drawn-out conflict. According to US officials, Caine showed maps in the Situation Room detailing how B-2 decoy bombers would distract Iran while a “strike package” moved in undetected to target nuclear sites.
The result, dubbed “Operation Midnight Hammer,” caused severe damage to Iran’s nuclear infrastructure and triggered only limited retaliation—none of which caused American casualties. Caine’s ability to guide the president through the operation in real time, explaining each step and calmly answering questions, earned him a level of trust that previous military leaders under Trump often failed to secure.
A general who fits Trump’s mould
Caine’s influence is notable not just for his strategic acumen but also for how he communicates. White House aides say Trump appreciates that Caine doesn’t “drone on,” but instead gives direct, digestible answers. Trump himself has repeatedly called Caine “incredible,” and sources say the general is now a daily presence in Trump’s national security discussions.
Unlike his predecessor, Gen. Mark Milley—who clashed with Trump over politicisation of the military and whom Trump later publicly suggested should be executed—Caine has so far walked a careful line. At a recent press briefing with US Defense Secretary Pete Hegseth, Caine stuck to operational facts and avoided partisan comments, even as Hegseth praised Trump’s “brilliant” leadership.
Asked directly whether he had been pressured to skew his analysis to fit politics, Caine replied, “No, I have not, and no, I would not.”
A rapid rise and a test of balance
Caine’s ascent has been remarkably fast. After retiring in 2024 as a three-star general, he was recalled and confirmed by the Senate earlier this year as the first non–four-star and first retired officer to serve as chairman of the Joint Chiefs. Despite a MAGA-tinged legend Trump often tells—that Caine wore a campaign hat and pledged to “kill” for him—Caine told Congress that he never wore political gear or made such a statement.
Still, critics warn that the general’s closeness to the president could eventually blur lines between military professionalism and political loyalty. “There is a risk that this will be misperceived as becoming politicised,” said Peter Feaver, a Duke University professor and expert on civil-military relations.
For now, though, Caine’s measured tone, tactical precision, and loyalty to the chain of command appear to have struck a balance that satisfies both the White House and military brass. With Iran reeling and Trump celebrating a foreign policy win, the general known as “Razin’ Caine” is emerging as one of the most powerful figures in Washington—and a key architect of Trump’s national security strategy.
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