I recently finished reading an excellent book on piracy by Benerson Little, The Sea Rover's Practice. This is a great backgrounder on what really was behind the privateers, buccaneers / boucaniers, filibusters / flibustier, and pirates. Focusing on a hundred year period beginning in 1630, the former Navy SEAL draws on contemporary diaries and books to describe everything from the background, motivation, tactics, equipment, and even an appendix on drinks. The reality of the sea rover's tactics are in stark contrast to the image of the Hollywood pirate. The reality were crews and officers operating under very democratic rules and performing complex operations seeking to maximize effort (return on investment).
Appropriate to the modern era of small wars? Little generally leaves it to the reading to connect to the present (absent a rare couple of modern analogies in the book), except for one paragraph at the end:
Whatever their vices, weaknesses, and moral ambiguities, these buccaneers have in common with most sea rovers several tactical virtues, including innovation, loyalty, perseverance, adaptability, and courage. Collectively, they prove that a loose, uncentralized, and informal network can conduct significant, complex military operations. They show the effect that an irregular force can have on the resources of a powerful state, causing great economic damage and tying down significant forces. And, most importantly, they demonstrate that elements of broadly divergent and disparate cultures, races, nationalities, classes, professions, and personalities can act as one with a common goal.
My brief comments here don't do the book justice. The amount of detail Little puts in this book is sometimes mind boggling, not to say amazing. This is not a book that only looks at the past but has a surprising applicability to modernity. I have found it particularly useful in supporting various arguments about privatization of force as well as insurgent warfare.