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Winston Churchill is remembered as perhaps the greatest prime minister in the history of Great Britain. By the steel of his will, he led his island nation to stand against Hitler and eventually triumph in World War ll. But years before that victorious moment for the ages, Churchill found himself plunging through a succession of devastating trapdoors–each one worse than the one before.

In August 1929, Churchill had managed to bring in approximately $70,000 into the family coffers. That’s a lot of money even today. In 1929, that was an unimaginable amount of money for a single month’s work. He invested nearly all of it into the American stock market. He then jotted a note to his wife saying how pleased he was to finally reach a place of financial independence. Less than ninety days later the stock market fell through it’s own trapdoor and Churchill lost virtually everything.

It was a major blow. Churchill had experienced ninety days of financial security–and then the bottom fell out. For the first time in his adult life he had been on easy street enjoying the prospects of a comfortable future and then the trapdoor fell open beneath his feet and down he went.

That setback alone would be enough to send most any man into the dungeon of depression. But there were two more difficulties that waited quietly and patiently for Churchill to arrive. In 1931, after serving his entire adult life as a central figure in the British government, he was not invited to serve in the cabinet. This was another staggering blow to Churchill. He had been banished to the political wilderness. While Hitler was working full-time to build his war machine, Churchill, virtually the only British politician who saw the reality of Hitler’s threat, was put out to pasture. When he should have been center stage, he was banished to his country home where he wrote, painted, and built brick walls and cleaned out the ponds to stay busy. The great statesman was sent down to the minors to play Class A ball when he should have been starting in the All Star game. This defeat was even more bitter than the financial loss. It was heating up in the British steel furnace.

And then in the same year, while he was trying to hold things together financially and fight off depression of political defeat, he decided to take a tour of Canada and the United States. In New York City he looked the wrong way while crossing a street and was hit by a taxi traveling at thirty-five miles per hour. The accident sent him to the hospital, clinging to life by a thread.

In less than three years he had suffered three shattering transitions that had devastated him financially, then politically, and then in an accident that nearly cost him his life. In a letter...

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