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“The young, evolving Churchill was sure he would die early and had to accomplish great things, not be the loser his father proclaimed him to be”

“To get the brilliant Churchill,” says Carlo D’Este, “you had to take the human, flawed Churchill, the man obsessed with making something of himself.” In Warlord: A Life of Winston Churchill at War, 1874–1945, D’Este, a retired U.S. Army lieutenant colonel and acclaimed military historian (Bitter Victory: The Battle for Sicily, 1943) and biographer (Patton: A Genius for War and Eisenhower: A Soldier’s Life), looks at Britain’s fabled leader through a revealing lens: how the military background of this descendant of the Duke of Marlborough shaped his paradoxical character—and thus his fateful decisions during World War II. Unsparing yet balanced, the detailed portrait that emerges is fluidly written, deeply informed, and often surprising.

Why Winston Churchill?
I looked at the spectrum of books about him; there was no full-length military biography. You cannot begin to understand your character unless you look at the entire life. I learned this writing about Patton and Eisenhower. You can define each of my biographies by one word. Patton: dyslexia. Eisenhower: poverty. For Churchill, it’s rejection, starting with his father, who ignored or belittled him. That drove him to greatness.

How did you start?
With what I call “the circle.” To delve into a character, go to folks closest to him. Of course, Churchill’s circle was enormous. But that generation wrote diaries, memoirs, letters. I pity biographers of the 21st century; e-mail disappears.

So you dove into archives.
From experience, I sensed there had to be something new—and there was. Sir John Dill’s papers turned up at King’s College: memos with Churchill’s minutes in red ink and Dill’s replies, which showed Dill was stronger than people thought. The Shane Leslie papers—nobody’s seen them before. Leslie was very bright: articulate, a good writer, a cousin who grew up with Churchill and admired him but saw his real character. He offers keys to Churchill’s childhood—the key to understanding World War II. [Churchill] grew up rebellious, doing whatever he wanted—bullying, cajoling—to get what he wanted. This is the ruthless Churchill of World War II, one of the most ruthless people I’ve ever studied. He had to be, for Britain to survive.

He was a child of empire.
Queen Victoria was the center of the universe, and he saw Britain as the guiding light of civilization. But the Empire was already on its way out. Beneath the surface in India and South Africa was its seamy side: money, power, greed. South Africa was the Empire’s Vietnam. But to his death, Churchill dreamed of reviving it.

And what of his role in the Boer War?
The young, evolving Churchill was sure he would die early and had to accomplish great things, not be the loser his father proclaimed him to be. The Boer War made him. His main virtue, consistent during World War II, was his ability to take advantage of situations as they came up. In his great train escapade, he, a journalist, took charge of defending a British train, was captured by the Boers, and escaped. He demonstrated undeniable courage and became a hero. Yet his dispatches early on say, “This isn’t gonna go the way you think. It’s not gonna be over by Christmas.”

A man of action and ideas.
[Arthur] Balfour said, “Churchill has 100 ideas a day, but only four are good.” Hell, who has four good ideas a day? And he was able to articulate them, to use that incredible, complex mind to get others to think from new angles. That’s amazing, and central to his leadership. It led directly to tanks, strategic bombing, and countless other technical developments in World War II.

His exploits led him into politics.
Because he was told he was worthless, and couldn’t spend money his family didn’t have to enhance his career, he went into the military to prove himself—and get into politics, which he was enamored of early on, one of the few paths open to him. He started as a glory hunter. The allure of the military got in his blood, and he never shed it. At age 36 he was First Lord of the Admiralty. He wanted to throw that away to command a small battle there was no prayer of winning. That’s his impetuous side that overreacts and makes bad decisions.

Between the wars, Churchill—the outcast backbencher—was briefed constantly on military matters. That was surprising.
It startled me too: he was better informed than almost everybody, while four prime ministers went wink-wink [and turned a blind eye]. They disliked him, yet his strongest critics, like Balfour, quietly said, “If it comes to war, this is our guy.” But in May 1940, he’s regarded as a short-term caretaker. The king doesn’t want him. Lord Halifax has to turn the job down—he’s smart enough to realize he’s not the right guy. They all respected Churchill’s leadership ability. They didn’t trust him, but they needed a son of a bitch to run the war.

Flaws and all, he was it.
He was a real enigma. One second he’s doing something absolutely brilliant, the next he’s doing something so stupid your mouth falls open. In World War I he co-invented the Royal Flying Corps and pushed for tank development; before and after the war he opposed increased military funding. As prime minister, he sets up a special office studying technical breakthroughs, but he’s always busy doing nutty things. Inspecting the loading cables of a convoy going to the Mediterranean! Micromanaging generals like [Archibald] Wavell in North Africa, telling him to blow up his wells—Wavell’s only lifeline!

He fancied himself smarter than his generals.
As a warlord he’s an unalloyed hero; as a military strategist he’s a nightmare. The classic story is Norway. For Churchill, invading Norway was like the pickle he ate for lunch that he couldn’t get rid of. For everyone else it was nuts. How many thousands of man-hours were wasted by the general staff and senior officers explaining what logistics is? He never grasped what a modern mechanized military needed to function. In some ways his mind was like a railroad switching yard, with tracks going off every which way, and he kept going off on little dead ends.

Like the list of fired generals.
Another great failing: he wasn’t a good picker of men. He admired heroes. The problem was his heroes were all one war removed, or were heroic but not great commanders. [Harold] Alexander, his choice for Sicily and Italy, was the classic example. No one would ever question Alex’s courage. But he lacked any strategic sense. Look at the Sicilian campaign: no higher direction at all, just let the boys go play.

But he kept things moving.
If you weren’t doing something you were doing something wrong. You just couldn’t explain to Churchill that action for action’s sake could be a recipe for disaster. Again, he had reasons. What he saw in South Africa and World War I, useless generals squandering lives, left him abso-lutely appalled. Those who call him a warmonger, well, be my guest—but it’s clear he didn’t want either world war. In 1930 he wrote, “Once you’ve unleashed the dogs of war, there’s no calling them back.” He understood the horror. He knew there were enough World War I generals left over to fill an auditorium. You can’t blame him for his grave mistrust, his sense that all generals were useless. But he couldn’t grasp that he had to let the good ones do their thing—like a rather obnoxious little man named [Bernard] Montgomery.

He distrusted authority—except his own.
Another aspect of the enigma: for all the squabbling and fighting, he never overruled the chiefs of staff. When they said no, it was no. The problem was, no didn’t mean, “Let’s move on,” it meant, “Let’s argue for days, weeks,” until he finally realized he wasn’t gonna win.

He won the war, then lost his job.
He didn’t bother to campaign; he figured, “They owe me.” I can see why he’d feel that way, but the public may have had a better sense of Churchill than he did.