US Defense Secretary Mark Esper, left, and Chairman of the Joint Chiefs of Staff General Mark A. Milley, testify about the Defense department budget during a Senate Armed Services Committee hearing in Washington, DC, on March 4, 2020.
Saul Loeb — AFP/Getty Images
June 26, 2020 2:59 PM EDT

Defense Secretary Mark Esper and Gen. Mark Milley, the Chairman of the Joint Chiefs of Staff, are approaching a crossroads where they may be forced to choose between appearing publicly loyal to President Donald Trump and keeping faith with the nation’s soldiers, sailors, aviators, and Marines, according to current and former Defense Department officials and senior military officers.

Three issues are coming to a head simultaneously that are pushing them toward that choice, the sources said: the promotion of Army Lt. Col. Alexander Vindman, decisions to rename military bases that now carry the names of Confederate officers, and banning Confederate flags.

Esper and Milley are already on thin ice with the president, the sources said, speaking on condition of anonymity to avoid inflaming the tensions. While the Pentagon prides itself on staying out of politics, the President puts a premium on personal loyalty and has been systematically removing officials throughout the government whom he suspects are undermining him, including independent inspectors general and the U.S. Attorney for the Southern District of New York, and trying to replace them with what one former administration official called “political lackeys.’

Last week, Kathryn Wheelbarger resigned from her post as a top defense international policy official when the White House dropped her nomination to a senior Pentagon intelligence post in favor of Bradley Hansell, a former special assistant to Trump and retired naval and Army Special Forces officer. The widely respected Wheelbarger had worked for the late Sen. John McCain, a frequent critic of Trump, and she is a friend of former defense secretary James Mattis, who has harshly criticized Trump’s response to the protests that have followed the death of George Floyd. Days earlier, Elaine McCusker, the Department of Defense’s acting comptroller, resigned after the Administration rescinded her nomination to the post. McCusker has previously had questioned Trump’s decision to freeze aid to Ukraine.

Esper, a West Point classmate of Secretary of State Mike Pompeo and Army officer who has been called “Yesper” and “Yessir Esper” by some current and former Department of Defense officials behind his back for his fealty to Trump, has contemplated quitting since he publicly broke with the president in early June over invoking the 213-year-old Insurrection Act to deploy troops to control civilian protests, three of the sources said. Trump was furious, but decided not to fire the defense secretary on the spot, said current officials who confirmed an NBC News and other reports.

Milley has although thought about resigning after he got into a shouting match in the Oval Office on June 1 with the president over Trump’s desire to deploy 10,000 active duty troops to the streets of Washington to quell largely peaceful protests after Floyd’s death. Based on the fact that Trump backed down, Milley concluded that he still has some ability to influence the president, but he has contacted friends and asked what they would do if they were in his boots, the sources said.

The most decisive issue for both men may be whether Trump, who has intervened in military justice cases, ordered the withdrawal of U.S. forces from Syria, and announced plans to redeploy some forces to Poland from Germany without consulting the military’s political and uniformed leaders, now blocks Vindman’s pending promotion. Vindman, who testified to the House impeachment hearings about Trump’s dealings with Ukraine, is in line for a promotion to full colonel. Trump fired Vindman from the National Security Council in February, months before he was due to leave, saying he was “not happy with him.”

Trump’s intervention is highly unusual, and if Esper allows Vindman to be dropped from the Army promotion list, “it utterly destroys his loyalty to the troops,” said one former senior defense official. On the other hand, if Esper sends the promotion list forward with Vindman’s name on it and Trump himself removes Vindman, “it still hurts Esper hugely,” the official adds. Milley, a four-star Army general, “is implicated, too.”

Separately, the Navy and Marine Corps have taken action to remove the Confederate flag from their installations in response to the nationwide protests over racial injustice, but Secretary of the Army Ryan McCarthy told reporters June 25 that the Army won’t fall in step with the other services without Esper’s approval. “The Secretary of Defense wants to make a uniform decision for the policy for the Department,” McCarthy said.

Although he hasn’t weighed in on the flag issue, Trump has threatened to veto proposed legislation that would require 10 military bases named for Confederate commanders to be renamed, and threatened up to ten years in prison for anyone arrested trying to take down a federal monument. He ordered Interior Secretary David Bernhardt to return a statue of Confederate Gen. Albert Pike to its pedestal in Washington after protestors pulled it down with ropes. “These Monumental and very Powerful Bases have become part of a Great American Heritage,” Trump said on Twitter on June 10.

The Army leadership, and sometimes local commanders, have been responsible for naming bases, and many military leaders and members of Congress, including some Republicans, oppose Trump’s inserting himself into the issue, in what some perceive as an effort to boost his re-election prospects. Similarly, decisions on statues have been a matter for the Interior Department or state and local leaders, not the President.

Some defense officials also are opposed to Trump’s plan to stage a military parade in Washington on July 4 while coronavirus cases are exploding again in California, Florida, Arizona, and several other states. “This isn’t an ideal time to be massing our forces in Iraq this the middle of a city and trying to draw big crowds,” said one of the defense officials.

While some current and former officials acknowledge Esper’s and Milley’s dilemma, caught between the commander-in-chief and their duty to the forces they lead, others are less sympathetic. “When you lie down with dogs, you get up with fleas,” said a former senior Republican defense official. “These guys all knew what they were getting into. Now the escape tunnel has caved in.”

Contact us at editors@time.com.

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