Trump’s New Joint Chiefs Chair Is A Savvy Political Operator

If there’s any question why President Donald Trump picked U.S. Army Gen. Mark Milley to be the next chairman of the Joint Chiefs — months earlier than expected — look no further than his sports radio interview before the 2017 Army-Navy football game.

“Take that Jets shirt off,” the Boston-area native and avid New England Patriots fan barked at a New York radio host. Responded the host, “C’mon, ‘cause you win all the time.” Milley fired back: “You can’t argue with victory, you can’t argue with stats. The winners write the history books, brother.” 

On Monday morning, Milley will become America’s top general. Many Pentagon insiders never considered the blunt, tough-talking paratrooper a leading candidate to become Army chief of staff, much less chairman. But those who know Milley say he is a keen political operator who managed his own meteoric rise through the ranks while advancing the interests of his various institutions along the way. 

A mammoth personality, Milley can command a room by rattling off random facts about historic battles in American history — usually peppered with obscenities. But he is equally known for digging into the minutiae of briefing materials with such gusto that his staff stopped giving him the supplementary detail usually included in briefing books — just to help keep meetings on schedule.

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“When he was with President Obama, he was ‘General Milley, the Princeton graduate’,” said one current Army officer familiar with Milley’s leadership style. “When he’s with President Trump’s team, he’s ‘General Milley, the hockey player’.” (Milley played defense for two seasons at Princeton — registering five assists and racking up 28 penalty minutes in 35 games, according to hockeyDB.com.)

Now, the question is how Milley will handle advising one of the most mercurial U.S. presidents in history, at a deeply unsettled moment in American politics and across the globe. Now in his third year in office, Trump has churned through three national security advisors, two defense secretaries, and a national intelligence director. He is on his second secretary of state. Meanwhile, his administration has lurched unevenly toward a possible conflict with Iran, sought and then rejected a withdrawal from Afghanistan, and carried out an escalating airstrike campaign in Africa — at a time when the Pentagon is supposed to be shifting gears to counter threats from Russia and China, not terrorism. 

“Will he shift for the president? Will he play for the president or will he be an honest broker about his opinion?” a former senior defense official said. “I expect he’ll be frank with the president.”

Milley’s predecessor, Marine Corps Gen. Joseph Dunford — and former Defense Secretary Jim Mattis — preferred to operate behind the scenes, staying off camera where Trump could not see them. But to many, it’s no surprise Milley caught the eye of the reality-TV-star-turned-president.

“He would play to the most senior person in the room,” the former senior defense official said. “That doesn’t mean that he doesn’t speak truth to power.”

The current Army officer emphasized that Milley’s ability to connect with an audience should not be confused with either partisanship or inconsistency. “He understands that Washington is a political playground and he’s dealing with political animals and in order to advance his intstitution’s interests, he’s got to be able to operate in that political space,” the officer said.

Milley’s rapport with the “winning”-obsessed president was clear from the start: Trump unexpectedly tapped him to replace Dunford in December, months ahead of when that announcement would typically be made. And Milley leap-frogged Air Force Gen. David Goldfein, widely considered to be the leading candidate for the post.

But this isn’t the first time Milley has wound up in a position he wasn’t expected to be in. As a three-star corps commander at Fort Hood, Texas, he was an articulate voice on national television after an Army specialist shot three people in 2014. He received his fourth star shortly thereafter, and jumped ahead of other four-stars when Obama, on the recommendation of then-Defense Secretary Ash Carter, chose him as Army chief of staff. 

Milley, a voracious reader, was seen as disruptive and non-traditional — someone who could shake up the status quo. The Army “didn’t have the intellectual firepower, it didn’t have the self-criticism, didn’t challenge themselves,” the former defense official said.

And when it came to readiness, said Patrick Murphy, a former congressman and Army undersecretary during the Obama administration, “He was like a bulldog on a bone.”

Milley took over the Army at a time when the military’s focus was turning from two decades of counterinsurgency focus to preparation for potential wars with near-peer competitors. After the 2016 election, he worked closely with then-Army Undersecretary Ryan McCarthy, confirmed last week as branch secretary, to shift the service’s purchasing priorities to keep up with emerging technologies.

“Milley drove the Army staff pretty hard,” the current Army officer said. “He was never afraid to question assumptions. He often would do public math and challenge the senior officers in the room or the action officers in the room about how they made their conclusions.”

He was also a driving force behind the creation of Army Futures Command, and the decision to put it in innovation-friendly Austin, Texas, not on an Army base.

As a one-star general in Afghanistan, Milley was credited with pushing Pentagon leaders to implement policy and funding to ensure wounded troops could be medevaced to a hospital within 60 minutes of an injury, drastically improving their chances of survival.

“He wears his heart on his sleeve and he really cares about the Army and the country,” the former defense official said. (One of the first things visitors to his home see is a Japanese flag over the mantle, seized by his father in the Pacific during World War II.) “Now, the way he does it sometimes irritates people because guys below him and around him think he’s a bully. But he does what he thinks is right.”

But chairman of the Joint Chiefs is a different job than Army chief of staff, especially under Trump, who both boasts of U.S. military might and expresses ambivalence about its use. Dunford and Mattis are seen to have played a mediating influence on a president with little foreign policy experience and impulsive instincts. 

At Milley’s confirmation hearing, Sen. Angus King, I-Maine, asked the general whether he would be “intimidated” by the president in the grandness of the Oval Office. Milley was unequivocal: “Absolutely not. By no one. Ever.” 

“I'll give my best military advice. It'll be candid. It'll be honest. It'll be rigorous and it'll be thorough,” he said. “We are not going to be intimidated into making stupid decisions. We will give our best military advice regardless of consequences to ourself.”

Current and former Pentagon officials say Milley knows the importance of working closely with the civilian secretary. The challenge that he — like all chairmen — will face is whether he can put personal and Army parochialism aside and represent the military as a whole. Milley’s ascension ushers the Army into a uniquely powerful moment within the Pentagon. Defense Secretary Mark Esper served in the Army and was the branch’s secretary before taking DoD’s top job. Milley retains his close relationship with the Army’s McCarthy. And Secretary of State Mike Pompeo, a close ally of the president, is himself a one-time cavalry captain who graduated from West Point with Esper. 

“Is he going to give his opinion or is he going to give the Joint Chiefs’ opinion?” the former senior defense official said.

For years, Milley has believed that Russia and China pose the biggest threats to the United States. Officers who know him expect that his focus will be on implementing the 2017 National Defense Strategy. 

But with an unsettled Middle East and increasing tensions in the Gulf — and a Secretary of State with a proverbial bullseye on Iran — it remains to be seen if Milley will be able to maintain that focus. 

“His challenges will be: keeping his loquacious character in check and maintaining his allegiance to the Constitution in an administration and a circumstance that seems to be flexible,” the former defense official said.

Patrick Tucker contributed to this article.

CORRECTION: An earlier version of this story incorrectly identified Milley as the III Corps commander during the 2009 Fort Hood shooting. He was commander at the base during the 2014 shooting at the base.