I am a very peaceful person by nature, so it’s something of a dichotomy that I’ve been fascinated by war most of my life. I’m one of those geeks who devour war books and watch documentaries whenever a new one appears.
Some wars and leaders have slipped through the cracks, but I still consider myself a novice expert on war leadership, the great, the tragic, and the catastrophically incompetent.
I’ve immersed myself in all things Winston Churchill, having read Martin Gilbert’s voluminous work on his life. I consider Churchill the greatest war leader and one of the most fascinating individuals in history. There aren’t enough words to describe him, ironically, for a man who mastered them.
Comparing Churchill to, say, Donald Trump is like comparing the crown jewels to a maggot-infested, rotting bag of garbage. But I digress.
Abraham Lincoln comes a close second. He was anguished, but also a genius, able to strategize, cajole, and persuade even his adversaries. He was a superb judge of character. And one of my favorite figures in history is Franklin Delano Roosevelt, whose leadership during war was historic in countless ways.
Then there are the cautionary tales, those leaders who sent men to die for muddied reasons. Lyndon Johnson and George W. Bush come to mind, though LBJ inherited Vietnam. Despite his achievements, Johnson will always be defined by that war, just as Bush will never escape the catastrophic blunder of Iraq.
But nothing in the knowledge I’ve accumulated compares to the spectacular, dangerous incompetence of Donald J. Trump as a wartime commander.
To me, history’s worst war leaders share a defining trait — they lack strategy and fail to understand war’s darker realities. James Madison, for example, never served in the military. He stumbled into the War of 1812 unprepared, with a tiny army, no coherent strategy, and a capital so poorly defended that the British burned it to the ground. Many historians question whether he understood what he was doing.
Now consider Trump. The reasons for war with Iran have shifted so quickly and erratically that it’s an affront to the country, and especially to our service members. Trump seems unable to remember from one press gaggle to the next Truth Social post what the conflict is about or what he’s doing as a leader — a feckless, clueless leader, I may add.
What we do know, because narcissism is Trump’s defining trait, is that he has spent his life stamping his name on everything. Most recently, The Kennedy Center. The U.S. Peace Institute. Even the facade of the Department of Justice. And, of course, his own gilded, schmaltzy ballroom.
He wanted a war — a big one. Not for America. Not to free Iranians. Not to eliminate nuclear threats. He did it for himself. He wanted the marquee. All glory to Trump, conqueror of Iran. A hero for the ages. Not.
Think about what distinguishes genuinely great war leaders. Churchill, arguably the finest in modern history, possessed qualities Trump couldn’t even spell (see: “Straight” of Hormuz), let alone embody.
Churchill mastered military intelligence. He had a real military background. He surrounded himself with brilliant generals. He was brutally honest with the British people about what lay ahead, famously promising “blood, toil, tears and sweat,” and in doing so forged unbreakable national resolve.
When Churchill was wrong, he admitted it, changed course, and marched forward. That intellectual honesty was one reason the Allies prevailed. He also recognized the human cost of war, describing its suffering as “grievous.”
Trump? The opposite in every way. Most obnoxiously, while Churchill honored the dead, Trump shows contempt, wearing a campaign baseball cap.
Like Churchill, Lincoln absorbed the trauma of war — 600,000 dead Americans. You can see it in his face, aged dramatically over the course of the Civil War.
Lincoln was almost deity-like in his leadership (Trump thinks he is the “chosen one,” but honest Abe and Jesus are having the last laugh). He held together a disintegrating republic through moral fortitude and political genius. He never confused his legacy with the national interest.
Honest Abe told the truth, consistently. When the war was going badly, he said so. When the costs were staggering, he didn’t sugarcoat them. That honesty forged the national will to endure.
James Buchanan, by contrast, is widely regarded as America’s worst war leader. Well, he doesn’t have that title anymore. Buchanan was passive, watching the Confederacy assemble itself. He failed through paralysis and denial. Buchanan at least understood the gravity of what was unfolding.
Trump appears constitutionally — both in his mental make-up and law - incapable of grasping the stakes of what he’s unleashed.
Then there’s the military contradiction. He promised no ground troops. Yet the Pentagon is now sending 3,000 troops from the Army’s 82nd Airborne Division to the Middle East.
Unlike Lincoln, Trump lies and obfuscates at every turn.
And that is his most profound failure as a leader. Because everything he says about this war, from here on out, will not be trusted. It will be questioned, corrected, and dissected, while Trump plays the American people for fools.
The road ahead is ominous, not simply because wars are bloody and unpredictable, and because Trump has never possessed, and cannot fake, leadership. He has no strategic patience. He seeks no counsel, relying on his “gut.” He has zero respect for sacrifice and no humility to recognize that history is ruthless toward leaders who treat other people’s children like “losers and suckers.”
Churchill understood all of that. Lincoln bore it in the lines on his face.
And then there’s Trump. He just wants his name on it, like everything else.
That, more than any tactical miscalculation or half-baked 15 point peace plan, is why Donald Trump has already cemented his place as America’s worst war leader, as James Buchanan smiles from above.
Trump selfishly chose this war for the worst possible reason.