Good Guy Pirates

Here's the rhetorical question that starts this all off: Was Robin Hood a good guy or a bad guy?
Everyone knows the answer is "good guy".  Yet he was an outlaw.  He broke the law, constantly.  We accept he is a good guy because we are told he is a good guy and because we are presented with his foes (Sheriff of Nottingham, Guy of Gisborne, and Prince John) as unequivocal rotters.  Does it matter that he became an outlaw after poaching a deer and then killing a man all because his youthful pride led him to anger and poor decisions?

Admit it, you think this guy is a hero.

Well, honestly that story has long since been replaced by the noble-in-exile outlaw story, so I suppose it doesn't, but the point is that Robin Hood and his Merry Men are outlaws, which makes them criminals and they rob people, which makes them criminals but we accept that they are fighting against bad guys so they are not "bad" in our estimation.  There is something comforting, I suppose, about the outlaw being loyal to a rightful king and fighting against an evil despot.
Yet this does not apply to pirates, it would seem.
Pirate fiction, whether it be written or visual, tends to paint pirates as bloodthirsty rouges, mean-spirited, rapacious, and of generally no count.  The main avoidance tactic is to make pirates into silly and lovable rogues in a comedy piece.
In order to have a heroic pirate you have to have a privateer, since privateers work for a government.

Can you spot the privateer in this picture?  How about the pirate?

Of course history, if you dig deep enough, provides ample evidence of pirates that were outlaws resisting what they saw as oppressive governments, such as the Navy that impressed men and refused to pay them after a voyage, merchant captains (including slave ship captains) that paid low wages, if at all, and were harsh with discipline, and even the nations to which the pirates had previously belonged.  We have ample evidence that the great Blackbeard might have been fighting against an England that had a new monarch of whom he did not approve.

William Kidd as history remembers him

Indeed some famous pirates began their careers as privateers, including Benjamin Hornigold, his protege Edward "Blackbeard" Teach, and William Kidd, who sent out with a privateering commission but turned pirate due to unfortunate circumstances.
Long before those men sailed the seas as gentlemen of fortune, Sir Francis Drake sacked Spanish colonies in the New World, and indeed the Spanish called him pirate and much later when the father of the US Navy, John Paul Jones, conducted terror attacks against the British in their own waters, he too was called a pirate by that nation.  Pirate or privateer, it really comes down to a piece of paper and whether or not you are being targeted by the holder of it.

Captain Kidd, a product of the imagination (of Howard Pyle, in fact)

What is a Privateer?
A Privateer is a privately owned ship holding a commission to seek out and attack shipping and commerce of a nation that is an enemy of the nation that provided the commission, and/or an individual holding said commission or crewing said ship.  The privateer was legitimized in its actions by a government (and possibly financial backers as well) through the issuance of a letter of marque and reprisal.  Effectively it was a license that gave a private individual/vessel the authority to make war on behalf of government of issuance within certain boundaries laid out in the letter itself.  Issuing letters of marque was a good way to increase the naval power of a nation without specific cost to the nation itself.  As part of the practice, a portion of the plunder would be given over to the government, or perhaps the financial backers, with the rest going to the crew of the ship.  There is a certain patriotism to the role of privateer, and yet a certain romantic freedom to the idea as well.  The privateer fights for the home nation (or indeed might fight for a different nation, since profit was the prime motive) but is legitimized by the support.

POTC:OST calls Barbossa a privateer, but the entire ship is full of Brit Navy so he's hardly a good example.

Privateers also make for heroic characters that get to basically act like pirates, but can be good and noble because their crew is not a bunch of bloodthirsty rogues out to rape and plunder.

Only they are, and that's the problem.  People have no difficulty accepting the heroic nature of the privateer captain fighting for King and Country, but the attitude and motivation of privateer crews is essentially the same as a pirate crew: profit and freedom from the onerous merchant/navy shipboard life.  Even if the crew is made up of patriotic persons, these are still private individuals and they want prizes.  But we can pretend they are Merry Men, and that takes the curse off it.  A special case is the pirate hunter.  Benjamin Hornigold started out as a privateer, became a pirate, and then accepted a pardon from Bahamian governor Woodes Rogers and ending his career hunting down his former pirate buddies.  The pirate hunter gets to be a romantic, heroic figure as well, thanks to pirates always being portrayed as vile, evil rogues (save for comedies, where it could go either way).

The thin paper line between legitimacy and outright knavery.

But this is all bollocks, because the only thing that differentiates a pirate from a privateer is a piece of paper and who is making the call.  All the letters of marque in the world do not change the enemy's opinion.  England's privateer is Spain's pirate, you see.  We can say that there is another difference, but now we are getting into the nitty gritty of it, the nuts and bolts, if you will.  Pirates, by virtue of taking up the life of high seas crime, are self-determined individuals.  From the buccaneers of Hispaniola to the sunset of the Golden Age, pirates entered into agreements when they joined crews, had full democratic decision powers within it, and elected their own leaders, but privateers less so.  The captain of a pirate crew held his position through popular election and only as long as the crew wanted him, while a privateer crew was through a contract and the captain had authority close to, but not as absolute, as a naval or merchant ship's captain.  Mutinies did happen.  Strictly speaking a pirate crew cannot mutiny because a pirate crew can also depose an unpopular leader.  At the same time it is the nature of humans that they set up ordered chains of command in any ad hoc grouping, and sailors are given to a routine life, so pirates and privateers could be counted on to mostly get on with the business of being fighting sailors with or without an admiralty court in some distant land handing down absolute authority.  This makes the privateer your beloved Robin Hood of the seas with his Merry Men being the crew of NOT bloodthirsty and rapacious rogues.  Centuries of bad press have made it so that the word pirate precludes heroism, by and large.  We all want to be one, it seems, but we don't want all the bad press that goes with it.  Thus the privateer becomes the solution to creating the heroic pirate captain we really want in our fictional work.  Whereas the image we have of the pirate captain makes us think that he cannot command without murder and fear as his allies, we can accept the privateer sparing the enemy's lives and the crew will not turn against the captain because they are not all bad people, just private individuals with a desire to fight for their nation.
Yes, it sounds pretty sappy and ridiculous when you say it out loud.

Having said all of that, I don't mean to suggest privateers are wimpy pseudo-pirates, because they are not.  Famed French pirate Jean Lafitte could serve as the model for Jack Sparrow, engaging in smuggling, open piracy, spying and serving as a privateer for multiple governments during his career.  Indeed he cut deals, not throats, and tried to maintain a good image as much as possible all while engaging in a variety of quasi-legal and downright illegal activities.  Yet he is the romantic hero played by Yul Brynner in 1958's The Buccaneer.
The aforementioned Benjamin Hornigold may or may not have started as a privateer, but was by all accounts a man of some scruples who preferred to not attack British ships (his home nation), was a pirate and who ended his career as a pirate hunter for the crown.

Sir Francis Drake, sailor, patriot, and according to Spain, a pirate.

Is a privateer really a better choice than a pirate?

Given everything I have said above, it would seem that the line between privateer and pirate is a thin and blurry one at best, and I believe this is so.  What the privateer offers is a good way to have all the cool trappings of a pirate without the image problems that we naturally associate with piracy.  It's to be expected, sadly, that we love the pirate image, but when pressed we all (well not me) tend to sheepishly admit that pirates were bad people, which is not an accurate assessment at all.  You say, "I like pirates.  I'd like to be a pirate." and somebody is going to say, "Oh, you want to be a murdering rapist thief?".  It's like suggesting that slavery is okay.  So you sheepishly admit pirates were evil people, but it's just not true.  Some pirates were evil people in the same way that some car salesmen are evil people.  Still, there is no changing hundreds of years of opinions, so the legitimacy of the privateer allows us to have our pirates and call them heroes if we like.
We can also focus on the privateer captain as the big hero without running into the problems of the fully democratic pirate crew.  Our privateer can be a rugged individual, perhaps former navy, that has his own quest and we don't feel a conflict with his having to keep control of a pack of backstabbing, bloodthirsty rogues.  But we still get the whole pirate attitude and style.  It's a win-win situation, really.

Henry Morgan sailed as a privateer against the Spanish in the 17th century, sacking Spanish towns and recruiting the buccaneers of Hispaniola to form an amphibious strike force, eventually retiring from a life of adventure to become Lt. Governor of Jamaica.  This is a picture of a twat from a rum bottle, not at all the man in question.