This Is What a Leadership Failure Looks Like

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Reader note: This isn’t political. At least, not in the mode of the Red vs Blue tribalism that seems to infect almost everything anymore. But, if politics is the lens through which you view most things in the news and culture, then this will certainly feel political. If that is the case, please keep in mind that is not the intent of this post. Rather, the purpose here is to discuss the effects of superior leadership at critical moments in which the political actors and situation are merely the source material for that discussion.

Also, this is the longest post I’ve written here to date. I know such a warning runs the risk of scaring you away from reading, but I think it only fair to let you know. Hopefully, you will find this a worthwhile use of your time. One of these days, I’ll get back to writing smaller, easier-to-digest posts. Today is just not that day.

Being a leader isn’t the same as being the Team Captain who stands at the head of the line of like-minded mates who are all pursuing the same goal. That is where the privileges of being the Leader may lie, but not the work. The work of leadership is in the persuading those who aren’t already on board to set their disagreements, misgivings, and even mistrust aside and join the effort to pursue the team’s goal. In those moments, leaders dig in their heels and rise to the occasion, confronting the forces of chaos that threaten to pull the team apart and wrestle those forces into submission. When leaders do this, they create inflection points, thereby changing the course of destiny by sheer force of will, exertion of effort, and wielding of skill. This is what leadership is and what leadership does.

In his leadership masterpiece Good to Great, Jim Collins‘ entire focus was studying the inflection points that defined how a good company suddenly separated itself from a similarly situated competitor and became great, thereafter sustaining excellence over an extended period of time. The conclusion of Collins’ research — which he was adamant applied to any organization, and not just for-profit corporate structures in the business world — was simple: The soil from which that destiny-changing course alteration grew according was an extraordinary level of leadership.

At times, events can have an inertia of their own, just like every physical object in the universe. Like a modern airliner set on autopilot, events have the thrust of historical forces behind them and a heading where those forces will ultimately end up if no extraordinary intervention occurs before then. Here are two historical examples to illustrate this concept in real terms:

1. Lt. General Matthew Ridgway Takes Command in Korea – December, 19501

On Christmas Eve of 1950, Lt. General Matthew Ridgway (above, left) landed in South Korea to take command of a situation that was dire. General Douglas MacArthur had ordered Ridgway to leave his Pentagon desk job2 and assume command of the 8th Army in Korea after its commander, Lt. Gen. Walton Walker, had died two days earlier in a jeep accident. In reality, the expectations of Ridgway were pretty simple and hardly ambitious: lead the 8th Army and other United Nations forces in a retreat while inflicting as much damage as possible on the advancing Chinese forces.3

What Ridgway found when he arrived in Korea was an exhausted and demoralized force that half expected “to be pushed into the sea.” But, instead of leading a retreat, Ridgway climbed in a jeep and drove along the front lines, visiting his soldiers and learning what they were suffering the most: lack of hot food, nothing with which to write home, and freezing hands. Fixing these problems were among Ridgway’s first acts as commander: “he ordered an immediate remedy for the situation, with field kitchens to be moved forward to provide plenty of hot food, stationary flown in by helicopter, and a large supply of gloves for their hands.”

These were more than simple acts of compassionate leadership. They were tangible evidence to the men on the front lines of the 8th Army that Lt. Gen. Ridgway understood what they were going through and cared about their circumstances. The sight of Ridgway regularly riding in a topless jeep at the front, “sharing the snow, sleet, mud and freezing cold with them,” produced a profound psychological and morale effect. This change, forged through the application of Ridgway’s leadership, turned a demoralized and retreating army into a fighting force capable of going on the attack. By mid-March, 1951, those same troops — who had been despirited with “bugout fever” in December — had rallied under Ridgway’s leadership and succeeded in retaking Seoul, pushing the Chinese Communist forces back across the 38th parallel and into North Korea for good. Of Ridgway’s work in Korea, General Omar Bradley had this to say:

It is not often in wartime that a single battlefield commander can make a decisive difference. But in Korea, Ridgway could prove to be the exception. His brilliant, driving, uncompromising leadership would turn the tide of battle like no other general in our military history.”

Without a leader like Lt. Gen. Matthew Ridgway to seize the moment and create this inflection point, the historical forces of inertia would’ve continued apace. Here are just a few things that would not exist today had that been allowed to happen:

2. The Cuban Missile Crisis – October, 19624

“The Loneliest Job” – photo of President John Kennedy in the Oval Office by George Tames

On October 14-15, 1962, an American U2 spy plane flew high over Cuba and captured photographic evidence that the Soviet Union was in the process of installing nuclear-capable missiles on Cuba. The photos captured by that U2 flight were shared with President Kennedy on the morning of October 16, confirming the threat of nuclear missiles 90 miles off the coast of Florida with the ability to hit nearly every major population center in America within a matter of minutes. The “13 Days” of the Cuban Missile Crisis were underway — the most dangerous series of days humanity has ever experienced since time itself began.

Yet, even before that clock started ticking, there were forces already at work whose inertia would carry the US, the Soviet Union, and the rest of humanity over the edge into the abyss of cataclysmic self-destruction if left unchecked:

  • the natural progression arc of new weapons technology and its use5;
  • the fear (and political bludgeon) that Jack Kennedy was “soft on communism” just like his father, Joe Kennedy (who had proclaimed the Cold War to be “politically and morally bankrupt”);
  • the failed “Bay of Pigs” fiasco in April, 1961, which not only exposed President Kennedy as potentially in over his head, but also illustrated in blood the perils of half-measures when it comes to matters of war;
  • the public humiliation of President Kennedy by Soviet Premier Nikita Khruschchev two months later over the issue of Berlin during their summit in Vienna in June, 1961;
  • the upcoming mid-term Congressional election of November, 1962;
  • the public allegations made by political rival Senator Kenneth Keating (R-NY) in August, 1962, that the Soviets were moving missiles into Cuba … and challenging President Kennedy to do something about it.6

While these dynamics were playing inside Kennedy’s head as he tried to figure out how to respond, they also were undoubtedly at work in the heads of those advising Kennedy that a forceful military response against Cuba was the only answer. One the those heads belonged to General Curtis LeMay, the aggressive head of the Air Force’s Strategic Air Command and commander of America’s nuclear forces. General LeMay had invented the tactic of firebombing the Japanese population centers during WWII and believed a global thermonuclear war could be won if executed correctly.

On October 19th, during a meeting between the President and the Joint Chiefs of Staff at the White House, General LeMay pressed the case for an all-out military assault on Cuba, using the shame of Joseph Kennedy’s appeasement towards the Nazi’s to try to goad JFK into action:

GENERAL LEMAY: Now, as for the Berlin situation, I don’t share your view that if we knock off Cuba, they’re going to knock off Berlin. We’ve got the Berlin problem staring us in the face anyway. If we don’t do anything to Cuba, then they’re going to push on Berlin and push real hard because they’ve got us on the run. If we take military action against Cuba, then I think that …

PRESIDENT KENNEDY: What do you think their reprisal would be?

GENERAL LEMAY: I don’t think they’re going to make any reprisal if we tell them that the Berlin situation is just like it’s always been. If they make a move we’re going to fight. Now I don’t think this changes the Berlin situation at all, except you’ve got to make one more statement on it.

So, I see no other solution. This blockade and political action, I see leading into war. I don’t see any other solution for it. It will lead right into war. This is almost as bad as the appeasement at Munich.


Because if this [unclear] blockade comes along, their MiGs are going to fly. The IL-28s are going to fly against us. And we’re just going to gradually drift into a war under conditions that are at great disadvantage to us, with missiles staring us in the face, that can knock out our airfields in the southeastern portion [of the United States]. And if they use nuclear weapons, it’s the population down there. We just drift into a war under conditions that we don’t like. I just don’t see any other solution except direct military intervention … right now.

Despite all of these pressures pushing Kennedy towards actions that would’ve carried the world into the nightmare of nuclear war, the President found his footing and stood firm: the response would be a blockade, coupled with diplomatic pressure.

Kennedy’s commitment to this strategy was tested to the limit on “Black Saturday,” October 27th: while one American U2 was being shot down by the Soviets over Cuba, killing its pilot, Major Rudolf Anderson, another U2 piloted by Captain Charles Maultsby had mistakenly wandered off-course and spent over 70 minutes flying over Soviet airspace.

President Kennedy had every reason to overreact behind him, and multiple opportunities to justify issuing the order that would very quickly snowball into World War III in front of him. As author Michael Dobbs makes clear, Kennedy was consciously aware of the historical gravity of the moment, and wrestled with how history would judge his handling of it. By virtue of this long-term perspective, Jack Kennedy ignored the inertia of the moment and created an inflection point in history, steering the world away from bombing itself “back to the stone age” as General LeMay was known to say.

Because of the leadership that bent the course of history during those 13 days in October, 1962, this is not how New York looks today:

Which brings us to the events of the past week.

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Of course, this was not the first time KKK members, Neo-Nazis, and other believers in white racial superiority have gotten a permit to hold a public rally and exercise their First Amendment rights to assemble and speak. Nothing new there. However, it would be the first time for such a public spectacle in the midst of the political/cultural/sociological undercurrents of this particular moment in US history. Just as was the case with Kennedy in 1962, last weekend’s flashpoint set of events have preexisting but interrelated contextual currents flowing behind them:

  • the emergence of the Black Lives Matter movement in reaction to a series of fatal encounters between law enforcement and young black men;
  • the rise of a new breed of American left wing protest movements — from Occupy Wall Street to Antifa — whose activities have increasingly become less protest speech and more violent, destructive action;
  • the coalescing of ardent support of Donald Trump’s presidential campaign under the banner of the “Alt-Right,” a term loosely connecting a hodgepodge of groups, ranging from disaffected conservatives to muckraking meme-makers to “natural conservatives” focused on white identity politics … all the way over to virulent racists, neo-Nazis, and self-proclaimed “1488ers”;
  • the belief that Trump obliquely courted the support of white nationalists through Trump’s prodigious use of his massive Twitter platform over the course of his successful presidential campaign — whether this belief is actually true or not, it is simultaneously held by both Trump’s critics as well as the voices of the white nationalist strain within the Alt-Right. As a result, the belief is itself a contextual force with its own inertia irrespective of it’s validity;
  • the anti-semitic harassment of conservatives critical of Donald Trump by the Alt Right and the racial undertones of their favorite slur against Trump’s critics: “cuckservative”;
  • the loud and unambiguous accusations that Donald Trump is an actual racist. (Again, the presence of this as a historical force is completely separate from whether it is true or not.)

It is among these currents that the “Unite the Right” rally in Charlottesville, Virginia, took place. It is among these currents that the march by torch-light on Friday night, August 11, mimicked the aura of the Third Reich by evoking the imagery of its torch-lit parades of Stormtroopers. One of these currents — the increasingly violent Antifa movement — collided with this event in real time on Saturday, before the official events and speakers of the day could even begin. And, it is among these currents that an Alt-Right proponent of white nationalism drove his car into a crowd of counter protesters opposing the “Unite the Right” message of white nationalism, killing one and injuring 19 others.

Suddenly, this was not just another public KKK rally to be tolerated, maybe even protested, but then forgotten. A neo-Nazi murdered a woman for the crime of voicing her opposition to the idea of white racial superiority. This wasn’t a clash with the violent Antifa group that just got out of hand. To be sure, those had happened aplenty earlier in the day. But, when James Fields aimed his Dodge Challenger down the narrow street and mashed the accelerator, it wasn’t the violent black-clad, mask-wearing Antifa he was aiming at.

With all of these factors in motion, the historical inertia of this awful moment is clear: towards a deepening of the rift among Americans, with its ultimate destination being an eruption of violence that could well usher in a Second Civil War.7

It was into this moment full of inertia and pregnant with both risk and opportunity that President Trump stepped before the cameras last Saturday. The original plan for his remarks was to comment on the work done to address the many failings of the Veterans Administration. Instead, flanked by a handful of American Veterans there for the occasion, the news of the day demanded that President Trump issue his reaction to the events in Charlottesville.

For a leader to bend history, fortune favors the bold over fearful political calculation. For example, as President Kennedy faced those dangerous days in October, 1962, the political calculations all pointed in the direction of —

  • not looking weak compared to Khrushchev,
  • not taking a half-measure when using military force, and
  • not giving the Soviets anything as an inducement for removing their missiles from Cuba.8

As a result, JFK had to run a massive political risk in order to take the steps necessary to turn that moment into an inflection point and avoid the unthinkable which appeared to be inevitable.

On the other hand, the political risk President Trump would have to run to take a narrative-changing stand last Saturday was remarkably less. By employing his usual blunt and bruising rhetorical style, President Trump brought the full weight of the “bully pulpit” of the Presidency to the task of halting history’s inertia and forcing it into a new direction through the power of these words:

Ladies and Gentleman, before I get started discussing the great work that has been done to help our wonderful Veterans — truly great people, our Veterans — there is something else I must address first, unfortunately.

Earlier today in Charlottesville, Virginia, a terrible tragedy occurred as a lovely young woman was murdered and 19 other Americans were injured when a dumb coward drove his car into a crowd of people like we have seen in Europe so many times. I say a coward because that’s what he is. Using a car like a weapon like that an act of total weakness. Very terrible.

For sometime now, people who have supported me have been lied about by those on the left and in the dishonest media as being racists and bigots. This has been extremely unfair to a great many of honest, hard working Americans who supported my campaign as a way to have their voices heard. These people are very good people, and it’s sad how they’ve been unfairly treated.

But, let me make something perfectly clear: the losers we all saw parading around in Charlottesville last night and again today, chanting the ugliest, most despicable things about Jews and Nazi slogans — these people with their Nazi flags and their KKK outfits: they’re total losers. They’re just full of hate and have nothing positive to add to the conversation about how to make America great again. They may say they support me, but I don’t support them. They’re totally wrong, and I’m here to make sure they know it, and the rest of America knows it.

I mean, it’s very telling that these goofy people are marching around a town as beautiful as Charlottesville — a really beautiful place. Really. Thomas Jefferson’s home is there. Just a great place in America. But it’s just sad how these dopey losers are goose-stepping all over Charlottesville carrying the flags of the sides that lost two pretty big wars that we in America won. I mean, we literally fought two wars to defeat the evil of racism, and yet here these stupid thugs are, proudly flying the Swaztika and the Rebel flags.

Of course, I know there are many good and decent people who view the Confederate flag and statues of Robert E. Lee and others as pieces of southern history, and not necessarily symbols of hateful racism. I get that, and that’s a discussion we can and should have. But not today. Because today, we all know what was in the hearts of the people flying those flags in Charlottesville, and it wasn’t southern hospitality and history. These jokers made it plain as day by their words, their chants and their Hitler salutes: they think a white America is the best America, and to them I say … <leans into the microphone> WRONG.

The hate and the division must stop, and it must stop right now. We have to come together as Americans with love for our nation and true affection — and really I say this so strongly — true affection for each other. Above all else we must remember this truth: no matter our color, creed, religion, or political party, we are all Americans first. We love our country, we love our God, we love our flag, we’re proud of our country, we’re proud of who we are.

Of course, President Trump said none of these things.9

As has been noted by many, taking a firm stand against the KKK and Nazism is the easiest thing for any American politician on any level in either party to do successfully. It is, quite literally, what the captain of America is expected to do.

Mom, baseball, apple pie … and Cap fighting Nazis. #Merica

Even in the risk-averse world of modern American politics, this is the true “just leave your putter in the bag and pick it up” gimme putt — almost impossible to miss no matter how you approach it.


That is, until President Trump stepped up to the podium at his Trump National Golf Club in Bedminster, NJ, and swung his rhetorical putter:

We’re closely following the terrible events unfolding in Charlottesville, Virginia. We condemn in the strongest possible terms this egregious display of hatred, bigotry, and violence that’s on many sides. On many sides. It’s been going on for a long time in our country. Not Donald Trump, not Barack Obama, it’s been going on for a long, long time. It has no place in America. What is vital now is the swift restoration of law and order, and the protection of innocent lives. No citizen should ever fear for their safety and security in our society. And no child should ever be afraid to go outside and play, or be with their parents, and have a good time.

I just go off the phone with the governor of Virginia, Terry McAuliffe, and we agreed that the hate and the division must stop. And must stop right now. We have to come together as Americans with love for our nation and true affection — and really I say this so strongly — true affection for each other.

Our country is doing very well in so many ways, we have record, just absolute record employment, we have unemployment at the lowest it’s been in almost 17 years. We have companies pouring into our country, Foxcon and car companies, and so many others, they are coming back to our country. We’re renegotiating trade deals to make them great for our country, and great for the American worker. We have so many great things happening in our country, so when I watch Charlottesville, to me, it’s very, very sad.

I want to salute the great work of the state and local police in Virginia. Incredible people, law enforcement, incredible people. And also the National Guard, they’ve really been working smart and working hard. They’ve been doing a terrific job. Federal authorities are also providing tremendous support to the governor, he thanked me for that. We are here to provide any other assistance is needed. We are ready, willing, and able.

Above all else we must remember this truth: no matter our color, creed, religion, or political party, we are all Americans first. We love our country, we love our God, we love our flag, we’re proud of our country, we’re proud of who we are. So we want to get the situation straightened out in Charlottesville, and we want to study it. And we want to see what we are doing wrong as a country where things like this can happen.

My administration is restoring the sacred bonds of loyalty between this nation and its citizens, but our citizens must also restore the bonds of trust and loyalty between one another. We must love each other, respect each other, and cherish our history an our future together. So important. We have to respect each other, ideally we have to love each other.

And with that, in less than four short minutes and with less than 500 words, President Trump stepped out of the way and let the inertia of the destructive forces discussed above barrel past him without meaningful interference. The moment had passed for leadership to grab history by its horns, wrestle it to its knees, and create an inflection point towards a new direction.

To be clear: this is not to say that the President’s statement was bad in the sentiments it expressed — unity; love, respect and loyalty to our country and to our fellow countrymen; the long-running history of hatred and bigotry; the condemnation of violence; and yes, even the much-derided notion that political violence is a real concern from the far sides of both ends of the political spectrum. Expressing these noble aspirations and frank realities is not bad at all.

Unfortunately, it was a small statement ill-fitted for the gravity of the moment. With all of the currents running around issues of race and violence and President Trump’s campaign and his still young presidency, this simply wasn’t a moment for an above-the-fray, “many sides” are to blame posture for the country’s leader to take. There have been many opportunities to talk about the violence of the leftwing Antifa movement, and there will likely be many more to come, sadly. What made Charlottesville tragically unique — and the potential to become an inflection point of lasting importance — wasn’t that it was another episode of a Jets-vs-Sharks-style rumble between right-wing racists and left-wing communists.

In fact, President Trump’s words were so generic that if you listened to them and hadn’t yet seen the news, you wouldn’t have any idea what had happened. You’d be forgiven for thinking a young child had been murdered in front of her parents while playing in her front yard rather than that a white supremacist had deliberately used an increasingly popular ISIS-inspired terrorism tactic to try to murder dozens of Americans protesting racism. The President’s Saturday statement about Charlottesville gave far more attention to totally irrelevant topics like unemployment, the economy, and foreign trade than the crime for which he was there to discuss. Conspicuously absent were any words at all about —

  • the KKK, neo-Nazis, and other strains of white supremacy on display beneath their chants of “Blood and Soil!” and “Jews will not replace us!” which animated James Fields’ actions;
  • the fact someone had died — much less was deliberately murdered — and that she was a 32-year-old paralegal named Heather Heyer;
  • that 19 other people were injured while protesting against the hateful ideologies that animated the vanquished sides of both World War II and our own Civil War.

While much of the criticism centered on whether Trump’s generic words served as encouragement for radical elements of the Alt-Right, the bigger leadership miss was in the failure to speak directly to the fears of those who see the KKK and fear lynchings … or who see Nazis saluting by torchlight and fear gas chambers. While these people probably don’t support Donald Trump as President, they are nevertheless still Americans, and that alone makes them worthy of his empathy and leadership.

In the days that followed, the White House was hounded with questions about Trump’s statement, prompting him to issue a second statement on Monday. While this statement was very direct, calling out “the KKK, neo Nazis, white supremacists and other hate groups that are repugnant to everything we hold dear as Americans,” it didn’t matter. The moment to redirect the inertia of this horrible set of events had passed on Saturday. Monday’s statement was dismissed as an insincere reading of a teleprompter script, delivered under duress due to the intense political pressure. And then, Wednesday came, and whatever help Monday’s statement did was washed away thanks to a free-wheeling, off-script and combative Q&A session with the press in the lobby of Trump Tower:


After that performance, there can be little doubt that the destructive currents that preceded the ugliness of Charlottesville were strengthened. The people who see President Trump and his administration as being too comfortable with the racially-focused bigotry of the Alt-Right are even more convinced of this view. On the other end of the spectrum, the white nationalists of the Alt-Right interpreted the week in much the same way.

People often quote Dr. Martin Luther King Jr. in saying “The arc of history is long, but it bends towards justice.”10 But that’s not quite right. The “arc of history” doesn’t bend itself. It is bent by the choices of the men and women who in the great moments of history, grab its arc and force it in a new direction. It is bent by those who step forward and lead.

The value of having an experienced and capable pilot on the flight deck of a modern airliner is not for the periods of placid cruising at altitude, or even the routine takeoffs and landings.11 Where the pilot’s expertise really counts is in the moments of unexpected emergency, mounting stress and grave danger. Strong and capable Captains are needed the most when unplanned scenarios suddenly become undeniable reality, and the only way to turn the freezing river filling up the windscreen into a safe landing strip rather than a frigid tomb for the passengers entrusted to the pilot’s care is to pull off a piloting miracle.

The value of having experienced and capable leaders is much the same. By this measure of leadership, President Trump has proved himself this week to be not up to the task. Here’s hoping that changes soon.


  1. From this excellent book: Matthew B. Ridgway: Soldier, Statesman, Scholar, Citizenby George C. Mitchell
  2. He was serving as the Army’s Deputy Chief of Staff for Operation and Administration.
  3. In a communication to Gen. MacArthur on December 29, 1950, the Chairman of the Joint Chiefs of Staff wrote: “It appears from all estimates that the Chinese Communists possess the capability of forcing United Nation’s [sic] Forces out of Korea if they choose to exercise it. The execution of that capability might be prevented by making the effort so costly to the enemy that they would abandon it. … Since developments may force our withdrawal from Korea, it is important, particularly in view of the continued threat to Japan, to determine in advance, our last reasonable opportunity for an orderly evacuation.”
  4. On this topic, I can’t recommend this book highly enough: One Minute to Midnight: Kennedy, Khrushchev, and Castro on the Brink of Nuclear Warby Michael Dobbs. The audiobook version is also quite good.
  5. Dan Carlin’s “The Destroyer of Worlds” episode of his podcast Hardcore History explains this idea extremely well.
  6. This was no small factor for Kennedy. As described by Michael Dobbs: “Kennedy’s immediate reaction on learning from Bundy that Khrushchev had double-crossed him was to sputter, “He can’t do this to me.” An hour later, he walked into the office of his appointments secretary, Kenny O’Donnell, and announced glumly, “Ken Keating will probably be the next president of the United States.”
  7. People have been writing about such an awful development for awhile now. One such example from the right is conservative radio host Dennis Prager, who asserts that we are already in the midst of our Second Civil War, albeit a “cold” one. For now …
  8. The thinking was rational: you don’t negotiate with terrorists or pay ransoms to foreign kidnapping cartels, as doing so proves their heinous tactics successful and insures more of the same in the future. When Khrushchev made his demand that removing Soviet missiles from Cuba would be predicated on the US doing the same with their Jupiter missiles in Turkey, Kennedy’s way out of the crisis without triggering nuclear war got a whole lot more politically complicated.
  9. Except the last paragraph. These lines were taken word for word from the end of President Trump’s actual statement.
  10. This quote was a favorite of President Obama’s, but it is not a Dr. King original. Dr. King himself was quoting the 19th Century theologian Theodore Parker.
  11. While it remains true that airline pilots must be in full control during the takeoff procedure, “autolanding” is a more common thing than you might think.

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