In government work, one usually fails upward. Endless promotions, glad-handing, being able to properly read a room, these are the hallmarks of many people who comprise America’s elephantine Senior Executive Service (SES) or top-ranked military leaders, such as the current chairman of the Joint Chiefs of Staff, US Army General Mark Milley.
But the longer one remains ensconced in Washington’s unelected leadership; the more one enjoys their time as one of several mini-emperors of America’s Byzantine bureaucracy, the sloppier one gets.
Hubris leads to the fall of even the most skilled operators.
An Uncertain Trumpet
U.S. Army General Maxwell Taylor, a proud Democrat, ran afoul of Republican (and former US Army general) President Dwight D. Eisenhower. In 1953, Ike had instituted his “New Look” defense strategy which essentially called for massive cuts to the US Army in favor of what Eisenhower believed were “cheaper” and newer forms of national defense: Massive Retaliation.
Essentially, Ike wanted to cut the conventional Armed Forces significantly and invest heavily in nuclear weapons and AirPower, so as to decrease America’s overall investment in guns and increase her commitment to butter, or the civilian economy.
In 1955, US Army General Taylor was tapped to the Army Chief of Staff. He viewed it as his personal crusade to stop Eisenhower from accomplishing his cuts to the Army. According to David Halberstram in The Best and the Brightest, Taylor was “undercutting as subtly as he could Eisenhower’s massive retaliation, with testimony on the Hill, with subtle leaks to the right journalists.”
Sound familiar to General Milley’s relationship with Washington Post columnist Bob Woodward (and others)?
Ultimately, Eisenhower did not fire the insubordinate general. Taylor was allowed to finish his term of Army chief of staff and retired in 1959. In what would become a typical move for Washington insiders seeking retribution against political leaders they disliked or disagreed with, Taylor published a much-ballyhooed book, The Uncertain Trumpet, in 1959 and timed its publication to coincide with the opening of the new session of the United States Congress on January 6th of that year.
Due to his writing, Taylor did not stay retired for long. The general’s scathing criticism of Eisenhower, the Air Force, and the “New Look” caught the attention of Senator John F. Kennedy (D-MA), who was running for president in 1960 by campaigning against Ike’s legacy. General Taylor would prove essential in JFK’s campaign.
After his electoral victory against Eisenhower’s vice-president, Richard M. Nixon, JFK would eventually become embroiled in the Bay of Pigs disaster. In response to what JFK believed was poor advice from the US military, the young president created the role of “military representative” to the president. Taylor was given this unique role, due to his previous opposition to the Eisenhower strategy of Massive Retaliation. After a year of serving in this unique position, Taylor would eventually be promoted to the chairman of the Joint Chiefs of Staff and the special position of military representative to the president would be abolished by JFK.
Taylor’s insubordination and freewheeling in defense of his branch of the United States Armed Services got him the plum job of JCS Chairman in the Kennedy Administration. Inevitably, Taylor’s strategy of “Flexible Response” and his self-serving obsession with “counterinsurgency” would lead JFK and his successors into increasing America’s involvement in the ill-fated Vietnam War. All because this uniformed bureaucrat was skilled at reading a room and playing the Washington Insider game.
The Firing of Allen Dulles
This was precisely what happened to Allen Dulles and several of his colleagues who had pioneered the US intelligence services in the aftermath of the Second World War. Dulles had become accustomed to his status as one of America’s patrician “Wise Men”, one of those men (usually from a wealthy Northeastern family who attended one of the handful of Northeastern preparatory schools and who graduated from one of America’s Ivy League universities, like Harvard or Yale). When an upstart young Democratic senator from Massachusetts, John F. Kennedy, became president he was steamrolled by Dulles and many of the “Wise Men” into authorizing the anti-communist invasion of Fidel Castro’s Cuba. What followed was the Bay of Pigs (or, Bahia de Cochinos) fiasco.
JFK unceremoniously fired Dulles and punished many of the cocky bureaucrats who had populated Washington’s postwar national security establishment. He further threatened to “break the CIA into a thousand pieces” for what JFK viewed as their repeated failures.
Ultimately, JFK’s threat to the doyens of Washington’s Administrative State ended the day he was assassinated. In a final humiliation to the assassinated president, Dulles and other bureaucratic foes of JFK were selected to head the official investigation into President Kennedy’s assassination (known as the Warren Commission). It was as though the bureaucracy was insinuating the real professionals were having to be brought back inside after JFK had wrongly terminated their employment–all to investigate how that president was killed.
Other presidents, such as Richard Nixon would rise to challenge the bureaucratic establishment.
So, too, would Ronald Reagan, Bill Clinton, and Donald J. Trump. All of them in one way or another were either coopted or ultimately stymied by the permanent bureaucracy. These leaders were viewed as outsiders who threatened the status quo in Washington.
Creating Context
During the tumultuous final year of Donald J. Trump’s controversial presidency, as has been documented in various media outlets such as the recent Bob Woodward and Robert Costa book, Peril, US Army General Mark Milley was quietly undercutting President Trump.
Whether it be embarrassing leaks to specific journalists or talking to Trump’s domestic political rivals, such as Speaker of the House Nancy Pelosi (D-CA), or the military leaders of American rivals, such as Milley’s counterpart in China about the forty-fifth president’s mental state and strategic intentions…Milley was violating all kinds of standards and rules for a man of his rank.
When I worked in government, I witnessed one occasion where a very well-connected bureaucrat needed to be fired but the political leadership could not easily get rid of him. After one particularly egregious mistake, I was told by my boss that “everyone knows he needs to go. But we can’t fire him. It’ll create a media shit-storm that we don’t need.”
Shocked, I insisted that the individual couldn’t remain in his current position–and just bouncing him to another office would be just as damaging as leaving him in his current position. My boss nodded in agreement and said simply, “He’ll be gone soon.” I wanted to know how. My boss responded, “We’re creating context for his removal. Once the media buys into that context, we can kick him to the curb, and no one will bat an eye.”
Within a few weeks, the plan worked. This individual had aggravated both sides and quickly found that he did not have any allies to protect him. His partisan activities had also gotten him in trouble with the same media types who previously would have protected him and prevented our office from firing him. Unlike the private sector, sadly, government employees–particularly high-ranking ones–cannot just be fired for cause. There is a process and it is very political.
Milley did a good job of ingratiating himself with the media elites. As I noted in a previous article at this site, General Milley is a political general. He believes he’s good at reading political trends; at picking the winning side of any partisan fight. In the summer of 2020, Milley was already concerned with former President Trump wanting to deploy US military force against violent mobs protesting the killing of George Floyd while in police custody.
Although, Milley was still photographed in his fatigues marching alongside an energized President Trump as the leaders of the administration marched through the recently cleared streets of Washington, D.C.’s Lafayette Plaza. Trump had ordered the race rioters who had attempted to burn down the historic St. John’s Cathedral to be cleared out with tear gas. The nation’s Left wing erupted in anger after images of Mr. Trump holding a bible before the burned out church appeared. Anyone photographed with him became a target of their partisan ire. Including General Milley.

As I argued in the previous article on Milley’s political actions, General Milley was enraged that both he and his uniform had been used in Trump’s brazen political grandstanding. Rather than voice his displeasure to the president, Milley went to work on him from behind the scenes. Thus, the leaking to Woodward, et al., the highly irregular conversations with Pelosi and his Chinese counterpart, and the weird insistence that key military leaders pledge their allegiance to Milley rather than Trump in those chaotic final weeks of the Trump Administration.
Once Joe Biden became president, Milley had some wiggle room. He and his new boss, Secretary of Defense Lloyd Austin, curried greater favor with their new political bosses when they got into a shouting match with gonzo Representative Matt Gaetz (R-FL) about “White Rage” and how the military should go after domestic terrorists. Yet, as I noted at the time, neither Milley nor Austin are “woke”. Everything they did was to secure the support of the otherwise anti-military Democratic Party establishment.
Milley seemed to be coasting from that point onward. That is, until President Biden implemented the chaotic US military withdrawal from Afghanistan. Operating against the judgement of his military chiefs, Biden ensured that the US military would be cleared out of Afghanistan, no matter what the conditions on the ground were, by the end of August.
What’s more, in the aftermath of the disastrous US withdrawal from Afghanistan, the Biden Administration forced its Pentagon to admit that one of its last acts in Afghanistan–a drone strike believed to have protected the besieged Hamid Karzai International Airport (HKIA)–did not kill any suspected terrorists at all. It had, in fact, murdered an Afghan family whose head of household actually worked for the Americans.
This was a drone strike that General Milley had proudly announced when it had occurred during the final days of the US presence in Afghanistan and had defended on international television as a justified, righteous strike. A few weeks thereafter, President Biden’s people were forcing Milley’s colleagues to admit that the strike was ill-planned, innocent people were wantonly murdered, and Milley may have been publicly defending a war crime.
There’s that context again.
This, as revelations of the extent of Milley’s involvement with the press during the last months of Trump’s presidency were being revealed to the wider world. Surely, the Biden Administration understood that, while Milley’s actions over the last year has helped them politically, having a chairman of the Joint Chiefs of Staff who is such a free agent is a liability in the long-run.
Yet, given Milley’s anti-Trump activities, the Biden Administration cannot simply fire the military chief. Or, at least they couldn’t until Milley’s recent testimony to Congress about the precipitous US withdrawal from Afghanistan. In those contentious hearings, Milley and several other Pentagon leaders, strongly testified under oath how opposed to the Biden decision to remove US forces from Afghanistan they were. The testimony was highly damaging to the Biden Administration during an already bad time for the forty-sixth president.
Like Icarus flying too close to the sun, it’s possible that Milley’s testimony about Afghanistan and his egregious early defense of the now mistaken drone strike that murdered an Afghan family are the final moments before the general’s wax wings melt beneath the glaring heat of the sun.
While Gen. Milley’s recent Afghanistan testimony did damage Biden politically, it also allows for the Biden Administration to create greater context necessary for removing the uncontrollable general. Milley is already hated by the Republicans. His Afghanistan testimony has now made several enemies out of the Democrats. His defense of the murderous drone strike in Afghanistan has made Milley an enemy of many third party observers.
Under such conditions, Biden’s removal of Milley would be welcomed by almost everyone.
Stand by for more. But I’d not be surprised if Milley was gone soon. Even if he’s allowed to finish out his time as chairman and retire as Eisenhower allowed Taylor to do, I seriously doubt that Milley will ever be able to replicate General Taylor’s political success simply because General Milley has so badly played his hand.