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Churchill went to South Africa to cover the Boer War as a journalist. The war had just broken out between Britain and the Boers. He was captured by the Boers and imprisoned. He managed to escape from prison and took the railroad into Portuguese East Africa. This feat made him a national hero. As far as I know, this was the only time he was "in jail".

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12y ago
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Q: Why was Winston Churchill sent to jail?
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