Why Trump’s top general is walking a tightrope on Iran

Why Trump’s top general is walking a tightrope on Iran

• Caine drafts Iran strike plans, keeps meetings private to avoid leaks
• He maintains Trump's trust, keeps a low public profile
• Caine urges military neutrality, avoids open confrontation

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As Chairman of the Joint Chiefs of Staff, Dan Caine has been overseeing the drafting of US military options for a possible strike on Iran. But instead of convening large meetings in the Pentagon’s most secure conference room, Caine has summoned senior Army, Navy and Air Force leaders individually to his office. The goal, according to officials familiar with the process, is simple: avoid leaks and attention in an administration obsessed with secrecy.

Behind closed doors, Caine has repeatedly raised concerns about the scale, complexity and human cost of a major military operation against Iran. Those private cautions stand in contrast to the public confidence projected by Donald Trump, who has spoken optimistically about how easily the US military could prevail, CNN reported.

Learning from the Milley years

Caine’s careful posture is shaped by what happened to his predecessor, Mark Milley. Milley frequently clashed with Trump during his first term, including over domestic troop deployments and rhetoric that alarmed allies. Those confrontations eventually left Milley sidelined and deeply mistrusted by Trump.

Determined not to repeat that experience, Caine has chosen a more restrained approach. He avoids openly contradicting Trump, rarely injects personal views into high-level discussions, and focuses on laying out military options rather than steering decisions. Critics inside the system say that caution sometimes looks like hesitation. Supporters argue it is the only way to retain influence with a volatile commander-in-chief.

Massive military buildup, quiet doubts

Even as Caine voices reservations internally, the US has assembled its largest concentration of military hardware in the Middle East since the Iraq invasion. Plans under consideration range from strikes on Iranian missile and nuclear sites to operations aimed at toppling Iran’s leadership.

During a lengthy Situation Room meeting last week, Caine reportedly declined to predict the outcome of a regime-change operation in Iran. Officials say he was far less confident than he had been months earlier when discussing a US operation in Venezuela that led to the capture of its leader.

Trust with Trump, distance from the press

Caine has worked deliberately to maintain Trump’s trust, even seeking office space at the White House so he could brief the president more frequently. He is now considered part of Trump’s inner circle, alongside US Vice President JD Vance and US Secretary of State Marco Rubio.

At the same time, Caine has avoided cultivating a public profile. He rarely speaks to the press and appears publicly almost exclusively at formal briefings. Under Defense Secretary Pete Hegseth, reporters no longer travel with the chairman, breaking with long-standing tradition.

Staying apolitical in a politicised moment

Caine has repeatedly told colleagues that his priority is preserving the military’s nonpartisan character. That instinct was evident last year when he privately urged senior officers not to cheer or react during a speech by Trump and Hegseth, warning them to maintain the same neutrality expected at a State of the Union address.

Yet Caine’s own rise was unconventional. Recalled from retirement and promoted despite never leading a combatant command, his elevation fuelled suspicion among some officers that loyalty was part of the calculation. Caine has denied that narrative, telling Congress that the military must “speak the truth to power” and resist politicisation from the top down.

A delicate balance with real consequences

Caine’s tenure has unfolded amid aggressive uses of military power, from overseas strikes to controversial domestic deployments. He has provided options for these operations while stopping short of publicly endorsing them. In private, he has occasionally pushed back, including questioning elements of the National Defense Strategy and urging an end to a costly campaign against Iran-backed Houthis in Yemen.

For now, Caine remains in place by mastering what many in Washington see as the hardest role in Trump’s second term: staying close enough to influence decisions, distant enough to avoid confrontation, and quiet enough to survive. Whether that balancing act holds if tensions with Iran tip into open conflict remains an open question.