The fact is that, as a man of the hard Left, Obama is more comfortable with a totalitarian Islamic regime than he would be with a free Iranian society. In this he is no different from his allies like the Congressional Black Caucus and Bill Ayers, who have shown themselves perfectly comfortable with Castro and Chàvez. Indeed, he is the product of a hard-Left tradition that apologized for Stalin and was more comfortable with the Soviets than the anti-Communists (and that, in Soros parlance, saw George Bush as a bigger terrorist than bin Laden).
Because of obvious divergences (inequality for women and non-Muslims, hatred of homosexuals) radical Islam and radical Leftism are commonly mistaken to be incompatible. In fact, they have much more in common than not, especially when it comes to suppression of freedom, intrusiveness in all aspects of life, notions of "social justice," and their economic programs. (On this, as in so many other things, Anthony Daniels should be required reading — see his incisive New English Review essay, "There Is No God but Politics", comparing Marx and Muslim Brotherhood theorist Sayyid Qutb.) The divergences between radical Islam and radical Leftism are much overrated — "equal rights" and "social justice" are always more rally-cry propaganda than real goals for totalitarians, and hatred of certain groups is always a feature of their societies.
Head on over and read the whole thing for a view into the mind of someone who really, truly, does not believe in freedom.