Jack Sparrow is the John Galt of my generation.
That sentence hasn't had a monopoly on my thoughts – I've been going about my business, of course – but I keep coming back to it. For those who don't know, John Galt is a character in Ayn Rand's novel Atlas Shrugged. He organizes a strike of the creative minds of his generation to try to undermine society, and the end of the book finds him delivering a lengthy speech in defense of Rand's philosophy, objectivism. He is in many ways the epitome of libertarianism.
But so is Jack Sparrow, as odd as that may seem. Think about it. What is the one thing Jack Sparrow wants above anything else? It's not riches or even women (though he'll take those things when they come within his grasp, of course). Jack is obsessed withouwith getting the Black Pearl back under his command. He is willing to kill for it, lie for it, even accept the (token) authority of his archenemy to get control over it.
And what does the Black Pearl mean to Jack? He puts it pretty plainly way back in the first movie, when he and Elizabeth are marooned on an island together:
That's what a ship is, you know. It's not just a keel and a hull and a deck and sails, that's what a ship needs but what a ship is... what the Black Pearl really is... is freedom.
Jack's utmost desire in the world seems to be to be a captain of the one ship that in his mind has come to represent autonomy to him. Even when the ship is out of his control, he always insists on being named its captain – to his great loss, as we learn in Dead Man's Chest. When he actually does face longterm subjection to another person (i.e. when it's not really a part of some plan he's working toward, he seems to get very agitated. Think for example how desperate he is to get off Davy Jones's ship in Dead Man's Chest, and how frustrated he is at being shanghaied by Blackbeard in On Stranger Tides. The other pirates around him, they don't like the situation but they also more or less accept it. For Jack, it seems to cause a more severe mental stress.
For me the final proof was in On Stranger Tides, where Jack loses his interest in the Fountain of Youth after he hears that it will require a sacrifice. Jack's not squeamish about taking someone else's life; he was ready to conscript a hundred men to Davy Jones' service in exchange for his own freedom. He hates Barbossa, too, and back in the original movie he kills him as soon as he knows Barbossa is mortal.
But the concept of taking another person's life – of doing that directly to himself, and of establishing so intimate a connection, a debt of sorts - that is a first-class turn-off for Jack. I think it's the connection that does it for him. (I also suspect it's a big part of why it's so incomprehensible to everyone, Jack included, that he once loved Angelica in On Stranger Tides.) Jack sees himself as a free man, and he's obsessed with staying that way.
The great irony is that by most measures, Jack is one of the least free characters in the movie. Barbossa is more or less secure inhimself; Jack is controlled by his obsession with the Black Pearl. Elizabeth is very much in control of her own decisions as much as any one of her gender could be, and she's very adept at twisting other people to her designs (Norrington in Curse of the Black Pearl, Jack himself at the end of Dead Man's Chest.) Will starts off the series as a blacksmith's apprentice who has more or less nonexistent freedom. He also lives just on the bounds of polite society so he is able to disregard it at need and then use it as a shield so he gets clemency rather than execution at the end of Curse of the Black Pearl. And in a much simpler sense, a ship, Jack is his own master only in the sense that Tom Bombadil is: he is lord of an ever-shrinking realm, incapable of controlling the topsy-turvy world around him.
There's a much simpler, sense, though, in which Jack's wrong to think of the Black Pearl as autonomy. It is, at best, autonomy for him; there are loads of other men – each alike in dignity to Jack – who serve under him, often in horrid and degrading circumstances. And that, I think, is another way that Jack is really like John Galt. This is the dark underbelly of libertarianism. We do not all have equal choices, we are not all free to make our choices. Would you say to the orphan or the person whose family could not afford to educate him, who was faced with poverty or piracy, that he had really made a free choice? The Black Pearl under Jack doesn't seem to have conscriptees in the same sense that (say) the Flying Dutchman does; but there is no denying that characters in these situations probably didn't have a whole lot of choices to begin with. Certainly they have not chosen to not be captains of their own. (Take Anamaria, for example, whose ship Jack stole and lost.)
Jack doesn't seem very concerned with people in these positions. It is their bad fortune, but simply not his concern. Yet another similarity with libertarianism: it is the John Galts, those oppressed and limited by a collective society, whose choice is sancrosanct. John Galt, indeed! Pirates can be a lot of fun as entertainment – but it's also pretty illuminating in its own way, or can be.