World Review
Trump's unusual pick for Joint Chiefs chairman walks a political minefield
By Dan Lamothe The Washington Post
Published April 1, 2025
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When President Donald Trump announced Lt. Gen. John Daniel Caine as his choice to be the country's next top general in February, it sent shock waves through the halls of the Pentagon. The president, in a Friday night social media post, said that he had fired Gen. Charles Q. Brown Jr. and other senior military leaders, and was appointing a retired three-star general as chairman of the Joint Chiefs of Staff.
Caine, 56, was a relative mystery man in Washington. He had never overseen a branch of the armed forces, led a major combatant command or managed a division with thousands of troops in combat. Some top retired military officers quietly worried whether Caine had curried favor with Trump or maneuvered himself politically to get the position.
Retired Gen. David L. Goldfein, the Air Force's top officer for most of the first Trump administration, said he and other former members of the Joint Chiefs - staffed by the four-star officers in charge of the Air Force, Army, Marine Corps, National Guard, Navy and Space Force - wanted to know for certain that Caine had not done anything to "politick for the position."
Goldfein, an F-16 pilot like Caine, said he raised the issue with the general directly and came away assured not only that Caine had acted professionally, but also that he had wrestled with whether he should take the job. In the end, Caine told Goldfein, he had found inspiration in a passage from the Book of Isaiah that seeks volunteers: "Then I said, 'Here I am! Send me.'"
Goldfein, who had been considered for the position himself during Trump's first term, noted the sensitivity of the moment and the long-standing norm that the U.S. military remain nonpartisan.
"I think once we were all confident that there was none of that going on … then it was, okay, now it's time to roll up our sleeves and do everything we can to help him be successful so the nation can be successful," Goldfein said of his fellow retired Joint Chiefs. "I know from our conversations, he's spending a lot of time thinking about the position and the responsibilities of the position."
Today, Caine will testify before the Senate Armed Services Committee at a confirmation hearing. It remains unclear how or why Trump selected him for the job, what the vetting process was or when Caine discussed the matter with Trump before his announcement. The role has proved challenging for previous chairmen under Trump - raising the question of what it would take to hold the position for a full four-year term now.
Caine did not respond to requests for comment. Defense Secretary Pete Hegseth has fiercely defended the president's choice, saying Caine is the "man to meet the moment."
Brown, who was appointed chief of staff of the Air Force by Trump in his first term, was removed Feb. 21 after a drumbeat of criticism from Trump's advisers, including Hegseth before he was appointed as defense secretary. The general, who is Black, raised their ire by promoting diversity programs.
Brown's predecessor, Gen. Mark A. Milley, clashed with Trump repeatedly, notably when the general apologized for appearing with the president outside the White House in June 2020 after federal forces had cleared protesters from Lafayette Square following the police killing of George Floyd. Trump has continued to criticize Milley, and in January, Hegseth removed his security detail, suspended his security clearance and requested a Pentagon inspector general inquiry into his behavior as chairman.
The first chairman under Trump, Gen. Joseph F. Dunford Jr., kept a low profile, but the president grew increasingly tired of him, too, officials close to Trump have said. He announced Milley as Dunford's replacement in December 2018, effectively undercutting the general nearly a year before he was due to retire.
Caine, who goes by Dan and the call sign "Razin" - as in, "raising Cain" - will face questions from senators about the recent controversial use of Signal, the commercial messaging application, by Hegseth and other senior Trump administration officials to discuss highly sensitive policy deliberations and operational details about a bombing campaign in Yemen.
He is also likely to be pressed on a number of other issues that have divided the American public: the administration's crackdown on diversity efforts; the purge of numerous senior military officers; the militarization of the U.S.-Mexico border; and the pressure campaign on Ukraine to negotiate a peace deal with Russia, on what many see as unreasonable terms.
The general's business interests may also be an issue for Democrats on the Senate Armed Services Committee, including his time as an adviser at Thrive Capital, an investment firm run by Joshua Kushner, the brother of Jared Kushner, Trump's son-in-law. No allegations of wrongdoing have been made about Caine's brief role at Thrive, but his unusual selection for chairman after retirement introduces business conflicts of interest that otherwise would not exist.
Caine will face the moment without the experience of his predecessors.
U.S. law states the president may appoint a Joint Chiefs chairman "only if" they have been a vice chairman of the group, or a four-star officer overseeing an armed service branch or major unified command. The law, however, also allows the commander in chief to waive those requirements if he determines doing so is "necessary in the national interest."
Caine comes in at a "significant disadvantage," said Richard Kohn, a professor of military history at the University of North Carolina. If confirmed, Kohn said, Caine will need to quickly establish confidence among the Joint Chiefs while also navigating the polarizing politics and fire-breathing rhetoric coming out of officials in both the White House and Pentagon.
In recent weeks, Trump has suggested he could seize Greenland and Panama by force and briefly floated the idea that the United States would take ownership of the Gaza Strip.
"It requires," Kohn said, "some situational awareness."
Caine, who is likely to be confirmed by a Republican majority in the Senate, joined the Air National Guard after graduating from the Virginia Military Institute in 1990. Like his father, retired Col. Steve Caine, he wanted to be a fighter pilot and pursued a career flying F-16s.
On Sept. 11, 2001, he was a major in the D.C. National Guard at Andrews Air Force Base, just outside Washington. In an interview with the National Guard inspector general a couple of weeks later, he said he directed maintenance workers to get planes ready and take flight that morning in case it was necessary to take down any hijacked aircraft.
Caine deployed overseas in the aftermath of the attacks, flying in support of the war in Afghanistan shortly after the U.S. launched military action there in late 2001. In 2003, he deployed again as U.S. forces hunted for Scud missiles in Iraq, collaborating as a pilot with U.S. Special Operations forces on the ground, said Steven McShea, a retired National Guard officer who has known Caine since the 1990s.
"That's a very small, tight world," McShea said. "He was introduced to those guys and built strong relationships, and from that point on … he kept getting pulled back into that world."
From 2005 to 2008, Caine served as a White House fellow and then a policy director to President George W. Bush on counterterrorism. He deployed to Iraq again in 2008 to serve as a commander in a joint Special Operations task force and then shifted to serve as a part-time member of the National Guard from 2009 to 2016. He pursued an eclectic civilian career in those years, including founding a small airline, Rise Air, and working as president of an aerospace company, Mayday Manufacturing.
In 2016, Caine returned to full-time military service. As a one-star general, he served as an assistant commanding general at the elite Joint Special Operations Command at Fort Bragg, North Carolina. Goldfein, chief of staff of the Air Force at the time, said he then sent him to Iraq to serve as deputy commanding general of a Special Operations task force.
It is in Iraq that Caine first encountered Trump, at Al Asad air base in December 2018. By then, the Islamic State terrorist group's main strongholds in Mosul, Iraq, and Raqqa, Syria, had fallen, but the militants retained control of a small amount of territory along the Iraq-Syria border. Trump has recounted the meeting on several occasions, with ever-changing details. Trump has said Caine told him that U.S. troops could finish the long campaign against the Islamic State in four weeks if they changed tactics, "but they just don't let us do our job."
At the Conservative Political Action Conference last year, Trump said that Caine "looked better than any movie actor you could get" and that he loved his call sign. "You're the man I'm looking for!" Trump said.
Trump recalled in the same speech that either Caine or a sergeant - it was not fully clear to whom he was referring - put on a red MAGA hat.
"I said, 'You're not supposed to do that. You know that,'" Trump recalled, acknowledging that military officers are directed not to engage in political speech while in uniform. "They said, 'It's okay, sir. We don't care.'"
Numerous current and former military officers who have worked with Caine have questioned the accuracy of that story, saying it is out of character. Caine, they said, is uncomfortable with praise, not a self-promoter and unlikely to allow colleagues to act in a political manner.
"We've got to operate between administrations, and we can't be seen as favoring one over the other," said retired Lt. Gen. Marc Sasseville, who has known Caine for more than two decades. "We purposely avoid those conversations - even with each other. And Dan has always been like that."
Caine remained under the radar in Washington after the Iraq deployment, getting a promotion to two-star general and running the Pentagon's highly classified "black programs," which are so sensitive that their existence is not acknowledged by the U.S. government.
He then served as the associate director of military affairs at the CIA, a liaison position that acts as a bridge between senior CIA officials and top military leaders. He held the position from November 2021 until December 2024, a period that included the onset of war in Gaza, Russia's invasion of Ukraine and CIA collaboration with Ukrainian spy agencies. Trump has said that President Joe Biden bypassed Caine for promotion.
If confirmed, Caine's biggest challenge will be "to establish himself in that universe of mighty personalities" among the Pentagon's most senior military officers, said retired Gen. Kenneth "Frank," McKenzie, who oversaw U.S. Central Command from 2019 to 2022. Top generals typically coordinate with the Joint Chiefs chairman before communicating with the defense secretary or president, he said, but that has not always been the case, and "each chairman will deal with that differently," McKenzie said.
McKenzie, who was director of the Joint Staff under Dunford, said Caine is up for the job, possessing an air of "fundamental confidence" while accepting criticism, hearing new ideas and drawing people to him.
When Dunford was chairman, McKenzie said, he ordered a National Defense University study to assess the common characteristics of a four-star general, including time in command, schooling and combat experience. It found no common denominator among those considered to be successful, McKenzie said, aside from intangibles like character.
"I would argue that's what Dan Caine has," McKenzie said. "Is he going to be successful? I don't know. I think it's impossible to predict any chairman's success because it is a uniquely difficult job."
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