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PLAYING SECRETARY

New York magazine

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June 16-29, 2025

As he sends troops into Los Angeles and prepares for possible war with Iran, PETE HEGSETH’S PENTAGON is beset by infighting over leaks, drugs, and socks. How long will Trump stand by his man?

- BY KERRY HOWLEY

PLAYING SECRETARY

On Dan Caldwell’s 87th day as a senior official at the Department of Defense, he read some intelligence reports and prepped for some phone calls and ordered from the secretary's mess his favorite Pentagon lunch: “steak bites” with asparagus and mashed potatoes.

It was April 15. Pete Hegseth, Caldwell’s friend for more than a decade and the reason he had been elevated as a 38-year-old to the role of senior adviser, spent that particular Thursday at the White House rather than in the office. The two had met while working at a Koch-funded nonprofit. They'd knocked on doors in the Capitol Building years before Hegseth became a weekend host on Fox in 2017. Hegseth always said that if you want to talk to the president, you go on Fox & Friends, and as co-host, he invited Caldwell on to press for Koch-approved reforms at the Department of Veterans Affairs. When there was a chance that Hegseth might be named secretary of Defense, it was Caldwell he asked to help with the transition. Caldwell coached Hegseth for his combative confirmation hearings, and once confirmed, Hegseth told transition officials it was “crucial” that Caldwell be in the building as soon as possible.

In policy circles, Caldwell was known as a serious analyst, a veteran committed to nonintervention and military restraint in ways that worried the bipartisan foreign-policy Establishment. When Mitch McConnell declined to support Hegseth’s nomination, he singled out Caldwell, who had written in support of “retrenchment” from the Middle East, a retreat from interventionism that alarmed the senator. Caldwell is six-foot-two with dark circles under his eyes and a military haircut, polite and professional, fluid in conversation but not given to laugh. On the day we met, he carried in his backpack a book called

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