Abstract: Contrary to much of the literature that depicts him first and foremost as a lifelong foe of communism, Winston Churchill was actually quite pragmatic regarding his opposition to various forms of totalitarianism, a worldview which explains his near-rabid anti-communism following the First World War and also his gradually softening change as he began to see fascist Nazi Germany as the greatest threat to a stable world order in the years before the Second World War.  It is this pragmatism and a basic hostility to tyranny, then, that best explains Churchill’s approach to all forms of totalitarianism.