Army Gen. Mark Milley headed to the White House in November to be interviewed for the top military job in Europe.
He emerged from the meeting with an even loftier prize: President Donald Trump asked Milley whether he wanted to be the next chairman of the Joint Chiefs of Staff.
Milley's steeper-than-expected promotion came despite the fact that then-Defense Secretary Jim Mattis was grooming the Air Force's chief of staff, Gen. Dave Goldfein, for the Joint Chiefs post. But Milley had champions in the president's inner circle, including Secretary of State Mike Pompeo and Trump campaign alumnus David Urban, who thought Milley's personality would jell with Trump's, according to four sources with knowledge of the meeting.
In the end, "POTUS was prepped to ask the question, 'Why not chairman?'" said one defense official who, like the others, spoke on the condition of anonymity to discuss internal conversations.
Milley faces his next crucial job interview Thursday, when the Senate Armed Services Committee holds his confirmation hearing. But the November episode demonstrated many of the traits that Milley would bring to the job: sky-high ambition, an ability to take over the room and a willingness to use his Trumpworld connections to get what he wants.
Few who know Milley, a 61-year-old who has seen combat from Panama to the Middle East, are surprised he's made it this far. Well-read and brash, Milley has had his eye on the chairmanship for years. POLITICO spoke to 13 people who have either worked with or for Milley, and the interviews portray him as a tough-talking warrior-thinker: He's Princeton-educated, an officer for whom books on Thucydides' Trap are "light reading." He's also a hockey player with a thick frame, stern gaze and boundless energy, known to bend others to his will.
"He's very thoughtful, very smart, very learned, reads a ton of books, very studied and is a big thinker," Urban, a friend of Milley's, told POLITICO. "He doesn't get credit for the big thinker part because he's got the tough hockey player exterior."
A former government official who has worked with Milley said the general's demeanor is a plus with Trump, who delights in spinning tales involving "my generals" who come from "central casting."
"I think that he ended up in the job in no small measure [because] there's a lot of aspects to him that Trump likes: He's loud, he's bombastic, he's salt of the earth, he is also at the same time Ivy League-educated," the former official said.
Retired CIA paramilitary officer Ron Moeller, who worked with Milley first in Afghanistan and later at the Pentagon, said he can see Milley meshing with Trump despite being "different in temperament and background."
"He tells the truth, even if it is unpleasant, and he listens as well — a rare trait among senior leaders," Moeller said. "He is loyal and repays that loyalty if he can. He's decisive. He's smart as a whip despite his gruff appearance."
Milley, now the Army's top officer, has already begun making an impact even beyond his current role.
He has spoken to Trump by phone about the southern border issue more than once, according to one Pentagon official — edging out current Joint Chiefs Chairman Gen. Joe Dunford. (The direct outreach is "completely out of the ordinary," the official said.) Blunt and loquacious, he dominates meetings in the Pentagon's secure briefing room, known as the "Tank," which sometimes grates on other top brass.
This spring, his intervention with then-acting Defense Secretary Pat Shanahan succeeded in heading off criminal punishments for officers who may have been at fault in the 2017 deaths of four soldiers during an ambush in Niger, two defense officials told POLITICO.
Like many top military leaders, Milley is less hawkish than some of Trump's top civilian aides, most notably national security adviser John Bolton — a trait that may mesh with the president's own reluctance to entangle the U.S. in overseas conflicts. But Milley has also publicly contradicted Trump's claims that transgender troops threaten the effectiveness of the military, in comments that opponents of the president's policy have cited in multiple court filings.
Some who know Milley acknowledge that he can "come off as a bully" — even by the standards of senior military leaders. He also has a tendency to micromanage and fail to see major decisions through, they say.
"He's probably a dominant personality because he already understands the dynamics, and so yes, to some he may be perceived as a bully," according to a person who has worked for him.
"Those people who worked for him I think feel a little bit bullied," said another former senior Defense Department official. "He was tough on them without necessarily giving them the decisions that they needed to get done what they were expected to do."
"There's not a lot of finesse with Mark Milley," the former official said, while adding that "he's smart and strategic, but he's also unconventional in his approach, which is what the military needs."
A spokesperson for Milley, Col. Kathleen Turner, declined to comment on the characterizations.
One aspect of Milley's leadership style that he may need to change is how quickly he handles incoming requests that require sign-off.
"A lot of things went into his office but didn't come out of his office," recalls the former official. "A lot of things just got stuck there. Sometimes he was decisive too quickly, other times he wasn't decisive at all."
Milley also wanted to be part of the approval process for every step of every acquisition program, which encompasses thousands of Army programs — an unusual approach for a chief of staff.
Yet as Army chief, Milley has been credited with pulling the service out of a "readiness hole," said Jeffrey Schloesser, a retired Army major general. Milley served as Schloesser's deputy with the 101st Airborne Division in Afghanistan.
Milley has testified that more than half the Army's 31 combat brigades are trained and ready for a major ground war — up from just three of the brigades when he took over as chief in 2015. With more money flowing into the Army under the Trump administration, Milley made boosting that number a top priority, as well as turning undermanned units into overmanned ones and building new adviser brigades to free up traditional units from small wars in Afghanistan, the Middle East and Africa.
Milley also takes to heart each of the 242 troops who have died under his command in Iraq and Afghanistan since 2001, including some who perished "within arm's reach of me," he said in a speech last year.
But Milley is also known to be fiercely protective of friends and of Army interests, as shown in his intervention into the Niger investigation.
Shanahan moved this spring to reopen the investigation into the 2017 attack, originally intending to appoint a general with the power to recommend criminal punishments for any commanders who were at fault, according to two defense officials. But Milley "talked him off the ledge," according to a military officer, and Shanahan instead appointed a different general whom Milley suggested, who lacked that authority. That general essentially prepared a "glorified book report" review of the investigations, the officer said.
Some people saw Milley's actions as a soldier protecting his own — Mattis and others had wanted to see high-ranking officers held accountable for mistakes that had been pinned on the lower ranks. But another Defense Department official said Milley "felt strongly that he didn't want the institution to get hung out to dry."
Turner, the Army spokesperson, said Milley did not weigh on in the scope of the investigation. "Gen. Milley provided his best military advice on the selection of the senior leader to conduct the review and how to best support the review effort, not the scope of the review itself," she said.
The investigation could still pose a problem for Milley with lawmakers, said Moeller, the former CIA officer.
"In my opinion, the only thing that could potentially trip Milley up during his confirmation hearings is the whole Niger incident," Moeller said. "The Army didn't do itself any favors with the fallout from that tragedy."
One area where admirers and critics see two different sides of Milley is with Trump's ban on transgender troops.
Milley caused major problems for the president's policy in April 2018, when he told Sen. Kirsten Gillibrand (D-N.Y.) that he had "received precisely zero reports of issues of cohesion, discipline, morale" caused by transgender people in the service. Trump's critics have cited those words at least 16 times in lawsuits against the administration.
Yet according to documents obtained by POLITICO, Milley took a much harder line on the issue during the Obama administration. At the time, he argued for a policy that would have disqualified the vast majority of transgender people from serving in the military, according to a memo that then-Deputy Defense Secretary Robert Work later sent to Mattis in June 2017.
"During policy development, General Milley argued we should require all transition plans to end with gender reassignment surgery to align 'top and bottom,'" Work wrote, referring to the service members' anatomy. Mattis had commissioned the memo to bring him up to speed on the debate as the Pentagon was facing a July 1 deadline to begin accepting transgender recruits.
Obama administration Defense Secretary Ash Carter had heard these arguments and "didn't find them persuasive," Work wrote. "As a practical matter, he rejected a requirement to compel sexual reassignment surgery as both overly extreme (statistically, only a small portion of the TG population seeks 'bottom' surgery) and illegal (we could not compel someone to have surgery if they did not need it)."
Milley also contended in a July 27, 2017, interview at the National Press Club that transgender service members had caused "a variety of issues" for the Army — the opposite of what he would tell Gillibrand the following year.
"The short answer to your question is, yes, we've had to deal with problems," Milley said during the National Press Club appearance, which occurred a day after Trump tweeted his opposition to transgender service. "We don't put it in the media. We deal with it professionally and quietly, with dignity and respect for the individual and the institution."
Turner did not respond directly to Work's memo or to the conflicting public statements, saying merely that Milley "participated" in discussions with senior leaders as the policy was being developed.
"He fully supports DoD's current transgender policy and has always believed the opportunity to serve should be afforded to anyone who can meet Army standards as outlined by existing policies, laws, and regulations," Turner said.
A Pentagon official who has worked with Milley said he suspects that the general hasn't changed his earlier views, and that when he answered Gillibrand's question he was already thinking ahead to his confirmation as chairman.
"He was angling to be chairman and he did not want to say anything that would damage his chances before the Senate," this official said.
But the Palm Center, which advocates on behalf of transgender service members, told POLITICO that Milley has evolved as he has learned more about the issue.
"It is no secret that Gen. Milley was not an early supporter of transgender service, so these 2017 documents are not surprising," Palm Center Director Aaron Belkin said. "After experiencing what open service was actually like, Gen. Milley never revisited his early concerns. Instead he confirmed that inclusive policy did not, in fact, compromise readiness, and he called repeatedly for respect for transgender service members.
"We give Gen. Milley credit for making that shift and acknowledging the success of inclusive policy," Belkin said.
Another Defense Department official agreed that Milley has truly changed his opinion as he learned more, and cites his speeches saying all of those who are qualified should serve.
"For a while, you're thinking, OK, he's got this talking point down, it's an inspiring speech, but does he really believe it?" the official said. "He really believes it. He really does. He'd write a lot of that stuff himself and it comes from the heart."
As chairman, Milley would not only be the highest-ranking officer in the military. He would also become Trump's principal military adviser. It's a relationship that's expected to go more smoothly than the one between Trump and Dunford.
"Dunford has almost no relationship with POTUS," said a Defense Department official, who added that the Marine general is seen by some at the White House as an extension of Mattis' "obstructionist" approach — prone to steering Trump away from his more extreme positions.
"The sense at the White House is that when Milley becomes chairman, the Joint Chiefs will not be nearly as confrontational with the White House," the official added.
Dunford's spokesman disputed those assertions.
"The statement from your anonymous source is inaccurate and ill-informed," said the spokesman, Col. Pat Ryder. "Gen. Dunford has a very effective relationship with the President and has ample opportunities to provide his military advice on a regular basis."
Those who know him say Milley won't be a "yes man" for Trump. Nor is he expected to push the president in a more hawkish direction.
As an example, the former senior Defense Department official cited a "really long" speech Milley gave at the Association of the U.S. Army's convention in 2016.
"It talked about the blood of war, and how difficult [war] would be," the ex-official said. "So in that sense, he might align well with the president, the president's instincts to avoid war and a lot of entanglements."
Dunford and Milley might not prove that different after all in how they lead the Joint Chiefs, said retired Marine Maj. Gen. Arnold Punaro, a former staff director of the Senate Armed Services Committee who is helping Milley prepare for his confirmation.
"I think he's going to be very much in the mold of a Joe Dunford and recent chairmen," Punaro said. "He's highly skilled, combat vet, very knowledgeable on policy, very knowledgeable on the building, has excellent working relationships with the other senior military leaders including the combatant commanders. … I think he's going to be a superb chairman."
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