FALL GUY

Trump Frustrated With Favorite General Over Consequences of His Own Actions

The president was apparently fed up with his handpicked general for not having a magic solution.

President Trump reportedly took his top military boss to task over a vital oil route remaining snarled as a result of his Iran war.

Trump, 79, is said to have leaned on Gen. Dan Caine, 57, to explain why battlefield dominance has not translated into instant control of the Strait of Hormuz, despite Caine having repeatedly briefed him on the likely closure of the waterway ahead of the war.

The New York Times reported Sunday that the president ”pressed” Caine in the Oval Office last week about why the Strait of Hormuz could not simply be reopened.

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The problem, as the Times reported, is that Iran can still threaten commercial traffic in the narrow waterway with small boats, mobile weapons and explosive devices, even after major damage to its conventional forces. The risk has kept many shipowners and insurers wary of sending tankers through the strait.

That has left the administration looking at a harder and slower fix. The option under discussion is to have the U.S. Navy escort commercial shipping through the strait. But the Times reported that such a plan would likely still be weeks away. It would require more ships, more defensive systems, and further attacks on the Iranian weapons that still menace the passage.

In multiple briefings ahead of the war, Caine had repeatedly warned Trump that Iran could respond to any American attacks by closing the strait, The Wall Street Journal reported last week. Trump is said to have responded by arguing that Iran would likely surrender before even having time to shut down the waterway.

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Reuters reported Monday that Trump is now pressing allies and partners—including Britain, France, Japan, South Korea, and China—to help secure the strait, including with minesweepers and other assets. About a fifth of the world’s oil and liquefied natural gas normally moves through the passage.

But the coalition Trump wants is not in place. Japan said Monday it has no plan to send escort vessels, while the Associated Press reported that no country has yet formally signed on to the effort. Trump is also threatening more pressure, including possible further strikes tied to Iran’s Kharg Island oil hub and even a delay to his planned China trip as he tries to force Beijing to take a side.

Iran is not signaling a climbdown anytime soon. Reuters reported that Tehran says it has neither sought a ceasefire nor negotiations and is prepared to keep fighting.

Trump’s apparent frustration with Caine is notable. He is not just the chairman of the Joint Chiefs of Staff but is one of the few senior military figures Trump has openly admired.

Reuters reported that Trump became fixated on Caine after meeting him in Iraq in 2018 and later described him as “a real general.” The president picked him last year for the military’s top uniformed role in an unconventional move that pulled him back from retirement.

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Caine took over as chairman of the Joint Chiefs of Staff on April 11, 2025. Before that, he was the CIA’s associate director for military affairs, having served mainly as an experienced F-16 pilot, weapons officer, White House staffer, and special operations officer.

The Daily Beast has reached out to the White House and the Pentagon for comment.

White House spokesperson Anna Kelly responded with a statement that did not address the question asked regarding the Strait of Hormuz, instead hailing Trump for his “courageous” war.

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Tom LatchemLead Global Correspondent

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