Churchill The Failure: The Paradoxical Truth About The Best And Worst Leaders

That story is true. Churchill warned against Hitler when no one was willing to listen, then led Britain from its most desperate hour to victory. But this version of history is also profoundly incomplete. If not for Hitler, Churchill would be remembered as a failure – if he was remembered at all. During his long pre-war career (Churchill was first elected to Parliament in 1900) he squandered his abundant talents by mistake after mistake. He destroyed his credibility through his advocacy of the disastrous Gallipoli campaign in World War I, policies on Ireland, mismanagement of the British economy during the interwar period, stubborn defense of the Nazi-sympathizing Edward VIII when he was forced from the throne, and most of all by his vitriolic and (even by the standards of the era) astonishingly bigoted opposition to Mahatma Gandhi and Indian independence.

Churchill’s record was so bad he was viewed as a negative indicator. His warnings about Hitler were actually used by his opponents in Parliament as evidence that, given his track record, the Nazis were probably not that dangerous. When Churchill was wrong, he was very wrong. And when he was right, he was very right. This extraordinary record of triumph and disaster illuminates one of the most important paradoxes of leadership: the best and worst leaders are often very similar.

Churchill was appeasement’s mortal enemy. He thundered, for example, that “Nazi-ism and all it stands for, will, sooner or later, have to be grappled with and finally crushed. It is no use trying to satisfy a tiger by feeding it cat’s meat.” The rhetoric is distinctively his – the only word for it is Churchillian. The problem is that he never said that. I altered one word – Nazi-ism. The real quotation begins “Gandhi-ism and all it stands for…” When you use the same rhetoric to oppose a genocidal dictator and a pacifist, it’s not surprising that people stop taking you seriously.

It’s important to understand the full depth of Churchill’s mistakes on India, the issue which almost destroyed his career, and did destroy his reputation. Churchill, in his own words, “hated” Indians, describing them as “a beastly people with a beastly religion.” When Gandhi was imprisoned by the British in response to his campaign of non-violent civil disobedience, the British authorities decided to negotiate with him while they held him. Churchill, enraged, called Gandhi a “malevolent fanatic” and fought in Parliament against the negotiations. He knew so little about India that he was humiliated in the debates and defeated by mid-1931. Characteristically, he refused to accept it and continued raging against his own party’s India policy for four more years. He alienated the Conservative leadership and marginalized himself so far on the extreme right that he was accused of attempting to become “an English Mussolini.”

Churchill’s attitude towards India did not change when he became Prime Minister. He presided over – and actively prevented any efforts to alleviate – the catastrophic 1943 Bengal famine, which killed 3 million Indians. When Churchill’s India Secretary and childhood friend Leo Amery asked him to do something, Churchill laughed about the prospect of shrinking a population that bred “like rabbits.” A horrorstruck Amery wrote that when it came to India, there wasn’t “much difference between [Churchill’s] outlook and Hitler’s.”

Churchill’s position on India was him at his worst. But his triumphs and failures were not the product of a “good Churchill” and a “bad Churchill.” They sprang from the same roots – principally his hair-trigger response to anything he saw as a threat to the British Empire and an unwillingness to admit defeat even when anyone else would have. Churchill did not change. His situation did. Churchill did what only Churchill would do. Sometimes that worked out, sometimes it didn’t, but it was always a product of his unique character. Only Churchill would have thrown away his career by fighting his own party on India for years after he had lost. But, similarly, only Churchill would have kept fighting in May 1940. In the right circumstances, there is no one you’d rather be led by than Winston Churchill. In the wrong ones, you’d rather have anyone else.

Just as we shouldn’t forget the depth of Churchill’s mistakes, we shouldn’t underestimate his singular contribution to saving the world from Nazism. When Churchill became Prime Minister, Britain’s situation – virtually alone against Germany, with France collapsing, the USSR allied with Germany, and the United States still neutral – was unthinkably desperate. David Lloyd George, the Prime Minster who had led her to victory in World War I, argued in Parliament that it was time to sue for peace, saying “People call me a defeatist, but what I say to them is: ‘Tell me how we can win.’”

The choice of if Britain should remain in the fight came down to a Cabinet struggle between Churchill and Foreign Minister Edward Wood, the Earl of Halifax.  Every major player in British politics preferred Halifax as Prime Minister to Churchill, but he had refused the position when it was offered (why remains unclear to this day). Halifax argued that Britain should seek mediation immediately, before France’s surrender and a German bombing campaign worsened its position. Churchill’s response was stirring: “nations which went down fighting rose again, but those which surrendered tamely were finished.”

Churchill’s rhetoric was powerful, but it was unlikely to move hard-headed statesmen like Halifax and Neville Chamberlain, who still lead the Conservatives, and the two united could push Churchill out of office. In desperation, Churchill rallied the Cabinet as only he could, proclaiming, “If this long island story of ours is to end at last, let it end only when each one of us lies choking in his own blood upon the ground.” The Cabinet responded with cheers, fortifying Churchill’s position enough to rally Chamberlain to his side. A day later, the news of the successful evacuation of British troops from Dunkirk arrived, sealing Churchill’s triumph and ensuring that Britain would not give in.

This isn’t just about Churchill. He is a perfect example of a much broader phenomenon. We say that leaders should have an impact. But having an impact requires doing something individual to you. If what you do is the same that anyone else would have done in the same situation, then you can’t have had an impact. So to be a high impact leader, you have to be different from normal leaders, so that you’re willing and able to do what other people would not.

The problem with doing things that no one else would do is that most of the time, there’s a reason no one else would do it. If it works, you’re a genius. If it doesn’t, you’re a fool. But most people aren’t geniuses. So when a leader decides to do something no one else would do, the odds usually aren’t in their favor. For example, suppose that a company on the point of bankruptcy brought in a new CEO who immediately kills 70% of its products over the protests of its Board. You wouldn’t expect success from that decision – unless you knew that CEO’s name was Steve Jobs. But you can’t count on hiring – or being – Steve Jobs. What makes high impact leaders distinctive is also what makes them dangerous.

As I’ve written about in a previous post, most organizations select their leaders via a careful process that filters out potential leaders who would take such individual – and risky – decisions. Leaders selected by such a process rarely have an impact because they are generally pretty interchangeable – like oatmeal. The brand of oatmeal you like makes some difference, how it’s prepared makes some difference. But in the end, oatmeal is oatmeal.

So it is with most leaders. But not all. Sometimes a candidate can be “Unfiltered” by slipping through this process and rising to power despite his or her uniqueness. In Churchill’s case, virtually every powerful person in British politics wanted Halifax to be Prime Minister. The system had looked at him and decided it wanted someone else. But when Halifax said he wasn’t available, Churchill was the only remaining alternative, and so the job fell to him.

And Churchill, as everyone from his biggest fans to his mortal enemies would agree, was unique. No one else could give his speeches. No one else would fight on for years when any rational calculation would say that the cause was lost. No one else would react to any hint of a threat to the Empire by rejecting negotiations and seeking to destroy it. Churchill’s distinctiveness made him indispensable to the fight against Hitler – and a catastrophe when dealing with India. But it was always the same Churchill. And as with Churchill, so with other high impact leaders. They are unique, but uniqueness is inherently a double-edged sword. Sometimes it makes them a brilliant success. Sometimes a catastrophic failure. And sometimes, like Churchill, they combine both in a single career. The best and worst leaders are almost always Unfiltered, and because of that they usually have far more in common than either does with normal ones.