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.
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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.
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