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Trump’s Handpicked Top General Took Legal Advice on Illegal Orders

Gen. Dan Caine, Donald Trump’s pick for chairman of the Joint Chiefs of Staff, reportedly sought legal advice about what a military commander should do if they receive an unlawful order.

Caine posed the question to Brig. Gen. Eric Widmar, legal counsel to the chairman of the Joint Chiefs of Staff, in November, after six Democratic lawmakers posted a video urging troops to “refuse illegal orders,” sources told CNN.

Widmar reportedly advised that a commander should request retirement but should not say the request was an act of protest or attempt to get fired intentionally.

President Donald Trump, Defense Secretary Pete Hegseth and Chairman of the Joint Chiefs of Staff Gen. Dan Caine in the Oval Office of the White House in Washington, DC, on December 15, 2025.
Concerns about the legality of the Trump administration’s deadly strikes against suspected drug boats have been raised for months. Andrew Caballero-Reynolds/AFP via Getty Images

Questions surrounding the legality of U.S. military actions have intensified for weeks after Defense Secretary Pete Hegseth was accused of issuing a “kill everybody” directive for a strike on an alleged drug boat in the Caribbean.

A second airstrike, which killed two survivors of the initial attack, has prompted accusations that it amounted to a war crime against shipwrecked individuals who were no longer a threat to the United States. The Pentagon has conducted more than two dozen strikes on alleged drug trafficking boats since that first one on Sept. 2.

In November, six Democratic lawmakers—Sens. Mark Kelly and Elissa Slotkin and Reps. Jason Crow, Chris Deluzio, Maggie Goodlander, and Chrissy Houlahan—appeared in a video reminding active-duty servicemembers that they can defy orders if they “violate the law or our Constitution.”

It was after that video that The Washington Post reported on September’s “double-tap” strike killing two survivors who were reportedly clinging to the burned wreckage.

Caine was not part of the operational chain of command that day, CNN noted, but is closely involved in operations under U.S. Southern Command and plays a larger role in presenting military options to Trump than Hegseth does.

In December, Adm. Alvin Holsey, commander of U.S. Southern Command, retired after 37 years in the Navy, after clashing with Hegseth over the legality of U.S. military strikes in the Caribbean, which have killed nearly 100 people.

Other senior officers, including Lt. Gen. Joe McGee, the former director for Strategy, Plans, and Policy on the Joint Staff, have also retired early amid Hegseth’s turbulent tenure at the Pentagon.

Defense Secretary Pete Hegseth (L), accompanied by Chairman of the Joint Chiefs of Staff Air Force Gen. Dan Caine (R), speaks during a news conference at the Pentagon on June 26, 2025 in Arlington, Virginia.
Pete Hegseth, a former Fox News personality, is said to routinely ignore input from intelligence and military officials. Andrew Harnik/Getty Images

Military officials and legal experts have questioned the advice Widmar gave Caine.

“A commissioned officer has every right to say, ‘This is wrong,’ and shouldn’t be expected to quietly and silently walk away just because they’re given a free pass to do so,” a former senior defense official who left the Pentagon earlier this year told CNN.

Dan Maurer, a retired Army lieutenant colonel and former JAG lawyer, said Widmar’s guidance appeared to “misunderstand what a servicemember is supposed to do in the face of an unlawful order: disobey it if confident the order is unlawful, attempt to persuade the order-giver to stop or modify it, and, if that fails, report it through the chain of command.”

“If the guidance does not explicitly advise servicemembers that they have a duty to disobey unlawful orders, it is not a legitimate statement of professional military ethics or the law,” Maurer told CNN.

The Daily Beast has contacted the Pentagon for comment via email.

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