As for political freedom, I think that for most people around the world the freedom to live, work, and raise their children in peace is freedom enough, and to hell with whatever else the government does.
Obama is your better in at least one sense: he is better at getting people to follow him. And you may rest assured that there are many people in this world who are your master in every field of endeavor. The same is true for all of us. The only man with no master is the dead man. As Dylan said, "You gotta serve somebody".
PS — I know Sulla was dictator prior to Julius Caesar; however, I chose not to mention it because he had neither charisma nor will to power. He later renounced the title (and the power that accompanied it) in favor of writing his memoirs. Gaius Julius did not, and with his dictatorship began the entity that became the Imperium. Furthermore I don't hold that the Empire was necessarily better in a moral or philosophical sense than were the Kingdoms; it was, however, a much more successful social system. It lasted 1,779 years, after all — and, some say, exists still.
The only man with no master is the dead man.
We'll have to agree to disagree there. I'm quite alive and far from alone. My only Master - well, you know Who that is.
Pulling back to history for a moment - the principal problem with autocracy is, as it has always been, one of succession. A representative government has many flaws, including placing some very flawed individuals in the role of decision-maker. What it does offer is orderly succession. (One might quibble at the notion that the circus we see before us constitutes "order" but it is, after all, far less disruptive than, say, the Wars of the Roses or the Thirty Years' War.) The country will survive a fool such as Obama placed into the chair that once held Harding and Carter because that fool must yield to the next without the citizens dying to effect it. And that is, after all, a form of order that autocracy, especially that of the Caesars, cannot offer.
Freedom is not an illusion, but it is a fragile thing and must be constantly and jealously defended. My point remains that the form of government is not irrelevant with respect to freedom, and that autocracy is inherently more oppressive than representative government. There too we must agree to disagree.
One other thing, though - the First Lie, "and ye shall be as gods" was not an expression of the relation of individual political freedom, or any other relation of man to man, it was an expression of the relation of man to God. That is the only autocracy acceptable to a free man. IMHO.