That's true, but this "anti-colonialism" thing is Dinesh's pet idea, something that he sees everywhere, so he's going to play up the theme.
True, D’Souza has written extensively about anticolonialism, but I heard Churchill historian James Humes (who does a bang-up one-man show about Churchill, too), talk about it in 2009. In the Q&A, the first question was about the return of the Churchill bust... Humes previously cheerful disposition clouded over immediately, and he discussed the subject brilliantly after that.
And when you compare 60s/70s radicalism, a thick layer of Marxism, and familial anticolonialism on top of that... voila - you have Obama.