Was Hitler a gambler or a planner up to 1939? for example, when he remilitarised the rhineland or 'anschlussed' with Austria, do you think his actions were planned or just gambled and why?

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Hitler was both a gambler and a planner. It was a gamble to re-militarize the Rhineland, to create the Anschluss with Austria through an obvious act of aggression (in spite of the fact that many Austrians welcomed him in), and finally, to demand the cession of the Sudetenland and further...

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Hitler was both a gambler and a planner. It was a gamble to re-militarize the Rhineland, to create the Anschluss with Austria through an obvious act of aggression (in spite of the fact that many Austrians welcomed him in), and finally, to demand the cession of the Sudetenland and further territory from Czechoslovakia. At any of these points the other powers could have stopped him, or at least attempted to. So each step was a gamble. But Britain and France did not have the will to confront him at those times, for various reasons.

Hitler deliberately carried out these plans when he did because he knew that he probably would not be opposed. In the 20 years following the massive carnage of World War I, there was enormous pacifist sentiment in the countries which had been on the winning side: Britain, France, and the US. Few people wanted to start another war and another round of bloodletting. In addition, and unfortunately, much of the British ruling class, and many people in the U.S. as well, had a sneaking sympathy for Hitler, or at least believed that Germany had been treated unfairly in the settlement after the Great War in the huge monetary debt it was made to pay. The French were averse to opposing Hitler as well, partly because of rampant anti-Semitism in France and partly because they believed their line of defenses along the frontier, the Maginot Line, was impregnable. As stated, Hitler had no way of knowing for sure that the other powers would not try to stop him. He also gambled that even if they did, he had built up his military and fired up the German people so much with his angry, victimized, and finger-pointing (chiefly against "the Jews," but also against the Allied powers he alleged were controlled by them) rhetoric that the Germans would have the will to win any new conflict that was initiated.

In 1939, when Hitler invaded Poland, many people were surprised that Britain and France finally stood up to him, even then. Not only had many of the conservatives in Britain been (mostly surreptitiously, but sometimes openly) pro-Hitler, or at least not anti-Hitler, but the political left in Britain initially opposed any new war. The reasons for this were that, first, Hitler had signed a non-aggression pact with Stalin in order to divide up Poland, and second, the assumption by much of the left was that this would just be another imperialist war, as World War I had been. By 1939, the Allies were completely unprepared for the German onslaught, as the Germans easily overran France the following spring, and the British forces on the Continent had to be quickly evacuated from Dunkirk.

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In matters of foreign policy, there is no way to separate planning from gambling.  When Hitler remilitarized the Rhineland or launched the Anschluss, neither he nor anyone else could have known how the Allies would react.  Hitler was sure in his own mind that he would get away with these things.  He was sure about this because of conclusions he had reached about the attitudes and the will of the French and the British.  This can be characterized as planning since this is all that leaders can ever do (unless they are lucky enough to have such good espionage that they know what the other side will do).

Therefore, we really have to say that Hitler was both a gambler and a planner.  We must also say that every leader has to engage in both planning and gambling because leaders can very rarely be sure of how an enemy or rival will react to what they do.

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