The Maniot pirates from the southern Peloponnes were said to be “the most barbarous pirates of the Mediterranean Sea” – a wild aristocratic oligarchy, expelled from their Byzantine homelands by the Ottoman military forces after the conquest of Constantinople in 1453. Piracy, however, was a rather common business in early modern times, licensed by the European states and deeply rooted within their strategies of warfare and expanding commercial trade. It had its own social and economic logics. The article tries to reveal these logics by the micro historical example of the rise and fall of the Maniot pirates, their practices and tricks, the surrounding landscape that made it possible, and the shifting political fortunes and allegiances of the Maniot clans, whose conservative patriotism played an important role in the Greek Revolution of 1821. Their decline in the 19th century partly came from inside, for instance from female moral criticism, and it was ultimately brought about by the patrols of superior international war-ships protecting the interests of free trade. For centuries, the Greek pirate economy successfully had filled a gap and prevented the eastern Mediterranean from slowing down. However, their early sea-capitalism of robbery and pillage damaged not only foreigners but also their Greek compatriots, and so it remained a fascinating phenomenon of transition, which in the long run failed to create more humane approaches to future social development.