Gen. Dan Caine, the chairman of the Joint Chiefs of Staff, had deep concerns about a war with Iran. He warned about devastating weapons stockpile depletion, flagged the dangers of the Strait of Hormuz, and kept pressing a single question during the deliberations: "And then what?" But at no point did he directly tell Donald Trump that the war was a terrible idea - though some of his colleagues believed that was exactly what he thought, according to a New York Times investigation, "Hvylya" reports.

Caine had earned Trump's trust years earlier by telling him the Islamic State could be defeated far more quickly than others had projected. Trump rewarded that confidence by elevating the former Air Force fighter pilot to the top military post and gave him the nickname "Razin' Caine." But the general was not a political loyalist, and the Iran war tested the limits of how far he would go in pushing back against presidential instincts.

During the deliberations, Caine shared alarming military assessments. A major campaign against Iran would drastically deplete American weaponry, including missile interceptors whose supply had already been strained by years of support for Ukraine and Israel. He saw no clear path to quickly replenishing the stockpiles. He also flagged the enormous difficulty of securing the Strait of Hormuz, which Trump dismissed on the assumption that the regime would capitulate before it came to that.

Caine differed from a prior chairman, Gen. Mark Milley, who had argued vociferously with Trump during his first administration and saw his role as stopping the president from taking dangerous actions. Caine's approach was to present options with their potential risks and second- and third-order consequences, then repeat that it was not his role to tell the president what to do.

The result was a dangerous ambiguity. One person familiar with their interactions noted that Trump had a habit of confusing tactical advice from Caine with strategic counsel. The general might warn about the difficulty of one aspect of the operation, then note that the United States had an essentially unlimited supply of cheap, precision-guided bombs. To Caine, these were separate observations. Trump appeared to think the second canceled out the first.

At the final meeting on Feb. 26, Caine laid out the risks and munitions costs soberly. He offered no opinion on whether to proceed, stating only that if Trump ordered the operation, the military would execute it. He told the president he had some time - the go-ahead was not needed until 4 p.m. the following day.

Also read: what critical weakness the Iran war has exposed to America's allies in Asia.