Dinesh D'Souza made a persuasive case that Obama was a committed anti-colonialist who was mentored by a real Bolshevik, Frank Marshall Davis, whose communism was unalterably opposed to colonialism or, if you prefer, imperialism. The British were the world's most accomplished imperialists and their empire included Obama's father's home country. In his autobiography Obama professes admiration for the legacy of his father who was also a rank anti-British communist.
For the record, I believe that British imperialism was on balance a good thing for the Third World then known as the undeveloped world and, especially when compared to the legacy of other colonial powers, was a great boon to those countries where it cultivated a respect for democracy, and respect for the rule of law, a sense of decency and overall fair play. The nations that emerged independence from the British Empire tended to be much happier places than those nations which had been colonies of other European nations.
As one poster as already noted, Churchill was clearly the greatest man of the 20th century. He is universally recognized for his indispensable role in marshaling national courage in Britain to stand alone against a rampaging Hitler but Churchill was very much responsible, perhaps more responsible than any man alive at the time, for committing the free world to a postwar coalition against a very rapacious Joseph Stalin. Churchill was in fact a lifelong anti-Communist as represented by his role in the immediate aftermath of World War I in which he supported the presence of British troops in Russia where they opposed the Bolsheviks until Churchill was rounded upon in cabinet and in the media as a warmonger.
Similarly in the aftermath of World War II, Churchill sounded the alarm against the aggressive imperialism of Soviet Russia in Eastern Europe and his famous "iron curtain" speech in Fulton, Missouri and, as in the aftermath to World War I, Churchill was rounded upon by the media and the left on both sides of the Atlantic as a warmonger. Churchill early advocated for a NATO structure which has held together ever since and it's as presented a united front to an aggressive Soviet Union and, despite its weakness, has proven to be one of the most successful and enduring alliances of all time.
As a communist himself, it's easy to understand why Obama despised Churchill whom he must've seen as a living impediment, just as he no doubt views the Constitution as a dead letter impediment to the advancement of socialist nirvana.
Finally, Obama is a racialist who no doubt associates Churchill with racism and believes it to be inextricably attached to his imperialism.
Churchill was a Caucasian, capitalist, anti-Communist, and the wrong image to tolerate because it might frustrate Obama's efforts to transform the United States and the world is something that Winston Churchill would have fought with every fiber of his being.
