I recommend Kevin Phillips’s book Wealth and Democracy. One of the more interesting things I learned was that many of the pirates in the Caribbean in the late 18th century were sailing out of Boston and Salem, tasked by the US government with capturing British ships, and that many of America’s great early fortunes were earned from piracy.

http://books.google.com/books?id=sPHP4uUFQgEC&lpg=PP1...

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Anyway, how do you decide who is the thief when we’re talking about stealing from boats trading in plunder, slaves, or products produced by slave labor, as was the case for an awful lot of what got shipped around the Atlantic for many centuries?

Though let's also be clear that piracy was often a legal activity by the pirates' home country, and that the offcial navy was engaging in the same activity - but they needed more help from mercenaries: the pirates.

Is Iraq with our Army and Blackwater mercs really any different?

That's true, many were. That was mostly in the Caribbean.

There were also (I would say the majority) private ships operating under a government licence, the letter of marque, where they could do anything to the enemy's shipping to "take, burn or destroy". That was mostly in the Channel and the south americas.

And there was a big grey area where a ship might be thieving on one occasion and operating under a letter of marque on another. As with most history, it all depends on who was telling the story afterwards.

That's not entirely true. Some were, sure, but it also depends on your perspective. Piracy was a way to wage war against foreign powers without openly declaring it. For example here is a Letter of Marque granted to Henry Morgan (the Captain Morgan) by the governor of Jamaica: http://www.piratedocuments.com/Letters%20of%20Marque/henry_m.... To the Spanish he was a pirate, but to the English he was a hero fighting against the Black Legend. Sir Francis Drake is another example of this. A really fun book if you're interested is Empire of Blue Water - http://www.amazon.com/Empire-Blue-Water-Americas-Catastrophe.... If you read it you'll see that pirates were actually a lot closer to modern entrepreneurs than you might think, except they operated in a much less regulated system.

Right, and there's a lot of good research into why people become criminals, and most do not do it because they're thrill seekers.

Instead, it mostly has to do with their expected costs and benefits, just like any other choice. If one comes from a poor background and lives in a society with poor upward mobility, your quality of life as well as life expectancy is low anyway, so the risk of crime is less severe compared to the expected gains.

No wealthy people became pirates. If risk aversion/attraction was all there was to it, they would.

Pirates were robbers, not thieves. Thieves steal by subterfuge, robbers by force.

This message brought to you by the Thief Anti-Defamation League.

So Robin Hood (if he really exist) is hero or thieves?