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Question: What was Churchills one great flaw or mistake!?
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One - - - I only get to pick one!? Churchill was one of the most greatly flawed GREAT men of history!. My personal choice for Man of the 20th Century!. The one flaw that tripped Churchill up many times was his ego!. His belief that every idea spilling from his brain was wonderful!. Many of his ideas were wonderful BUT coupled with reality they led to disasters such as Galipoli and several less publicized disasters!. Churchill believed in himself far beyond the capacity of the World to match him!. It is amusing to contrast Churchill with Hitler because both were the type to micro-manage the War, whatever war was being fought, but in Britain with its flawed yet workable democratic tradition there were checks and balances that kept Churchill's mistake from escalating into insurmountable disaster whereas in Nazi Germany Hitler became an insurmountable disaster!.
A final note - - - when someone corrected one of Churchill's lapses in judgment, there might be glaring looks and an angry cloud of cigar smoke but no more, and no ordering the offender off to face a death squad, whereas when anyone corrected Der Fuhrers mistakes Hitler would fly into a towering rage and heads would literally roll!. Britain won the War, Germany did not, what better argument for the British way of doing things!.

Peace/\/\/\/\/\/\/\\/\/\\\//\\//\\//\\!.!.!.Www@QuestionHome@Com

This muchly agrees with the above post!.

Churchill's greatest flaw was his idea that he was a strategist!. I would put closely behind this his limited abilities as a 'picker of men'!.

Churchill's military follies include Gallipoli, Greece, Crete and the 1940 Norway campaign!. He contributed directly by mismanagement to the loss of Singapore in 1942- Britain's greatest ever military defeat- and to the duration of the North African campaign over several years, instead of a few months!.

He hindered excellent generals- by his interference- such as Claude Auchinlek and Field Marshall Slim, while for too long promoting the plodding, abrasive Montgomery, the pretentious dilletante 'Boy' Browing, and he should have sacked the pugnacious abd brutal Arthur Harris in 1944!. Instead, when Bomber Command began utterly destroying cities as Germany's defences fell apart, he sought to blame others and plead ignorance, ultimately shunning the tens of thousands of men who fought in what was easily Britain's most hazardous and expensive campaign!.

Further, Churchill had a poor technical grasp, and many British weapons were grossly deficient because he listened too much to Industry in the conservative fashion!. Britain invented the tank but had the worst in the world all through the war, only producing a decent one in the final months!. He sent the battleships Repulse and Prince of Wales- without air support- to deter the Japanese, and they simply sank them with aircraft!. In his defence many of these problems were inherent in the British army's structure and doctrines!.

Churchill's gift was to have no concept of compromise to the Germans at a time when nearly everybody else in the world- except the disgusted British public- was happy to compromise!. He articulated this clearly and he had great authority and ability as a diplomat!.Www@QuestionHome@Com

Churchill's father never directed his reading nor his education, neither did his mother as both were too pre-occupied by their private distractions; Outside the United States, there are no free Libraries that the young can draw upon; Churchill's lack of a wide verity of reading material, led him into over-identification with the upper class; so was never able to identify with the lower classes, nor their needs; Churchill never learned Latin; so could never attend Oxford University and get an education which would have broadened his view of his fellow human beings!. So Churchill was of worthless leadership material, except in Times of War!. As soon as WWII was won, even though the War was not over yet, Churchill was rightly turned out of Office!.Www@QuestionHome@Com

He didn't hang Chamberland!.Www@QuestionHome@Com