Days after cameras captured him walking alongside President Donald Trump across a square near the White House that had been violently cleared of protesters, Army Gen. Mark A. Milley, chairman of the Joint Chiefs of Staff, sat in his office across the Potomac assessing the fallout.
Milley tried to explain that the episode had caught him off guard, that he hadn’t known Trump’s intentions when they walked into an area where just minutes earlier authorities had used tear gas to disperse protesters. Milley also knew that to the cold gaze of history, it might not matter.
“The whole thing was f---ed up,” Milley, loquacious and often profane, told others after the fact.
A former altar boy, Milley’s Catholic faith informed a feeling that he needed to publicly account for what occurred. “You confess your sins, do your penance, and you move on,” he later told a colleague.
Equally important, Milley believed he was one of the few officials who retained influence with Trump, who many aides feared would heed calls to attack Iran or drag the military into his quest to remain in power.
On a cold day outside the Capitol seven months later, Milley stiffly saluted a different commander in chief, one who promised to restore order but also harbored a deep skepticism of military influence and intended to sweep away many decisions, and some remaining officials, from the Trump era.
Milley, who declined to be interviewed for this article, is one of a handful of senior officials to straddle a fraught presidential transition characterized by conspiracy theories and violence. The success with which Milley navigates that transition will not only define his legacy, but also test whether the nonpartisan nature of the military’s most esteemed positions can survive a hyperpartisan time.
“He is one of the people who bear the scars of the Trump years,” said John Gans, a former Obama administration official who wrote a book about national security decision-making. “That may not be his fault, but that is the fate of being in the wrong place at the wrong time, which was being chairman under Donald Trump.”
'A tough guy'
Ice hockey helped Milley, who grew up in a working-class neighborhood outside of Boston, find his way to the Ivy League. He inherited the love of the sport from his father, a Navy corpsman who took part in the battle of Iwo Jima and brought his hockey skates to the Pacific.
Milley played hockey at Belmont Hill, a prep school outside Boston. Before he started there in 1972, his mother, who had served as a wartime Navy nurse, took him to a used-clothing store to get him a sport coat and tie. Milley was intimidated by the academics at the elite all-boys institution, but he excelled on the ice. He went on to play at Princeton, where he worked campus jobs, joined the ROTC and was an unremarkable student.
“I was in the half of the class that made the top half possible,” he later joked.
Moving up the Army ranks, Milley was known for having a big, commanding personality — and a burly physique to match. He relished storytelling and roasting peers. His willingness to make unorthodox decisions won him promotions.
“He has a sharp mind and had a vision for where he wanted to take the Army,” said a former senior Army official who worked closely with Milley and who like others spoke on the condition of anonymity to provide candid thoughts and recollections. “He’s also a blood-in-the-water type guy. If you let on fear, or if you don’t know your stuff, you’re going to get blown out of the water,” he said.
Detractors say he sometimes domineered those around him, allowed his temper to erupt and, according to another former official, “has an ego the size of the Empire State Building.”
In 2015, President Barack Obama nominated Milley to be Army chief of staff, vaulting him over more senior officers to the service’s top job. There, Milley sought to repair damage done by earlier budget cuts and prepare for 21st-century wars.
In 2018, he caught Trump’s eye as a possible replacement for Joseph F. Dunford Jr., the Marine general who served as Trump’s first chairman. Defense Secretary Jim Mattis, whose relationship with Trump was rocky by then, preferred Gen. David Goldfein, the Air Force chief of staff. But Trump did not connect with Goldfein, a pilot whose F-16 was shot down over Serbia in 1999. For one thing, a former Trump administration official said, the president didn’t like the look of F-16s. He preferred F-18s.
“He’s a hell of a brave guy. But the president asked what kind of airplane he flew,” the former official said of Goldfein. “These were the things that would go into his decision-making. Image was more important than anything.”
Milley, on the other hand, had the look and manner of a hardened infantry leader. The president was fascinated by Milley’s uniform, asking him what different ribbons and medals signified. “You’re a tough guy. I like tough guys,’ ” Trump told Milley, according to the former official.
A spokesman for Trump did not respond to requests for comment.
From the moment Milley became chairman in September 2019, he and Pentagon leaders were consumed by crises generated by Trump. Those included the president’s intervention in the Navy’s handling of a SEAL accused of war crimes and his greenlighting of a Turkish offensive in Syria, which endangered U.S. allies and necessitated a pullback so rushed that U.S. pilots had to bomb their own base.
Milley’s bluntness and combat credibility made him more effective with the president than some other top aides, current and former officials said.
When George Floyd’s killing by police sparked nationwide protests in May 2020, Milley and Defense Secretary Mark T. Esper pushed back against Trump’s desire to deploy active-duty troops on American streets. They sought to placate the president by placing combat soldiers outside Washington but hoped they wouldn’t be used.
On June 1, after Trump summoned Esper and Milley to the White House, he asked them to accompany him and a cohort of other aides outside. Milley, who was in combat fatigues, followed the president as Trump strode across Lafayette Square. There, the president, surrounded by other aides but not Milley, posed for the cameras and raised a Bible in front of a nearby church.
To critics, the moment suggested that the military supported the harsh treatment of protesters and Trump’s divisive approach to governing. Mattis, former chairman of the Joint Chiefs Martin Dempsey and hundreds of U.S. Military Academy alumni were among those who spoke out.
Current and former officials said Milley considered resigning but weighed that against his influence with Trump, who was already signaling he might not respect the results of the November election.
In an address the following week to graduates of National Defense University — the next generation of military leaders — Milley issued an apology unprecedented in recent military history.
“My presence in that moment, and in that environment, created the perception of the military involved in domestic politics,” he said. “It was a mistake that I have learned from, and I sincerely hope we all can learn from it.”
In the months that followed, Milley repeatedly spoke about the duty troops have to the Constitution and the rule of law, rather than to any person or political party. “We all committed our lives to an idea that is America,” he said in one message to the force.
Some officials thought Trump, angered over statements that were seen as an implicit rebuke, might fire Milley, who was slated to serve a four-year term. “If he gets reelected, you’re dead meat,” the former official told him.
But while Trump dismissed Esper in November, he left Milley in place.
Throughout the remainder of 2020, military leaders grew increasingly uneasy as the president suggested he might not respect the results of the election, raising the possibility of further crises involving the armed forces. To replace Esper, Trump tapped Christopher C. Miller, a little-known counterterrorism official, and several loyalists were installed around the acting defense secretary.
The last time Milley spoke with Trump was Jan. 3, when he visited the White House with Miller. Three days later, Trump supporters smashed their way into the Capitol in a riot that left five people dead.
Despite the criticism that the Pentagon should have moved faster to assist on Jan. 6, experts credit Milley with reinforcing the military’s nonpartisan status during the months surrounding the election.
“He’s the first chairman who’s had to answer serious questions about will there be a peaceful transition,” said Peter Feaver, an expert on civil-military relations at Duke University.
As Biden’s inauguration approached, speculation mounted that the new president might nonetheless ask Milley to step aside. In the past, a small number of chairmen have served shorter tenures, most recently when Marine Gen. Peter Pace stepped down after he was not nominated for a second two-year term in 2007.
But a senior administration official said such a move was never seriously considered. He said that Milley, as governing ground close to a halt during the Trump administration’s final weeks, helped spearhead security planning for Biden’s inauguration, when incoming officials feared supporters of the outgoing president might mount another attack.
“A lot of us have strong views about what happened at Lafayette Square, but we also have strong views that values the career of government and career expertise, including our military,” the official said. “And we have worked very closely and I think very successfully with Gen. Milley and many others who . . . served in the previous administration.”
This spring, Milley spoke with apparent relief about the restoration of what he called “regular order” in national security decision-making, including a return to frequent Cabinet meetings.
The renewed rhythm allowed him to make his case for keeping troops in Afghanistan, amid the new administration’s first major foreign policy debate. At the White House, Milley made an impassioned case that leaving could permit the Kabul government to collapse and provide a foothold for terrorists.
When Biden informed Milley and Defense Secretary Lloyd Austin, a retired general, in April that he had decided to withdraw, Milley sought to illustrate what he has referred to as the “saluting point” — where military officials stop making arguments and start executing orders.
Retired Adm. Mike Mullen, who served as chairman to Presidents George W. Bush and Obama, said that switching between commanders in chief was a familiar shift for career officers, who know they must provide advice and comply with decisions, whatever they may be. “That is literally a switch for us. It’s something that’s ingrained,” he said. “Whoever the president is, that’s what we go do.”
In another potentially revealing move, Milley recently changed his position on proposals to alter how the military handles sexual assault, dropping his opposition to stripping commanders of authority to refer cases to trial. The move reflected the failure of earlier efforts to curb sex crimes but also signaled he would not stand in the way of changes supported by Biden.
In addition to the shadow of Trump, another element Milley must negotiate as he seeks to make inroads with his new boss is Biden’s complex relationship to the military.
The president reveres those who serve, making frequent reference to his son Beau, who served in Iraq. But he also harbors deep skepticism toward military leaders based in part on the heated 2009 debates over Afghanistan, when he warned Obama against letting the generals “jam” him.
Biden’s selection of the seasoned but introverted Austin suggested his desire to avoid the foreign policy battles of the past, when the brass sometimes pushed back through the media.
Biden also prizes loyalty and personal relationships, suggesting he may keep Milley at a distance in favor of those with whom he has long worked closely, including national security adviser Jake Sullivan.
“He recognizes he’s operating in a challenging environment,” Jim Golby, a former Army strategist who teaches at the University of Texas, said of Milley.
Milley has previously compared his role to that of a stock broker who advises clients on different elements within their portfolio. “My job is to say, ‘Here is the cost and the risk, and here’s my recommendation,’ ” he said this spring.
So far, Milley’s directness, his speed in demonstrating support for presidential decisions, and his brio — mixing expletives with references to Xerxes or the Wehrmacht — appear to have smoothed his shift to Biden’s national security team.
“Milley’s a colorful guy, always has been. Biden’s a colorful guy, always has been,” a former senior military official said. “There are possibilities there in terms of things that are similar, that would connect them.”
Whether Milley eventually develops a close relationship with Biden, experts said the decision to keep him in place goes a long way to repairing the harmful politicization of the military that occurred under Trump. An early exit would have reinforced the idea that the armed forces are part of the political fray, a notion antithetical to the military ethos.
“There was certainly potential for a much nastier situation where he played an obstructionist role or the administration undermined him or ousted him. We haven’t seen that truly ugly outcome,” Golby said. “It was a real test of our system.”
Anne Gearan and Dan Lamothe contributed to this report.