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Politically, Leon Trotsky was Stalin's greatest enemy, because after Vladimir Lenin's death, Trotsky was supposed to succeed Lenin. Stalin managed to eliminate him as a rival for power, exile him and eventually have him murdered.

Militarily, Adolf Hitler was his greatest enemy, because Hitler had the German Army attack Russia in World War 2. The German Army nearly defeated the Soviet Union. Stalin might have been thrown out of power had Germany won.

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