The story of pirates and privateers was actually a tale of legalities and illegalities, separated by a thin statutory line marking those on one side as criminals and the other side as heroes worthy of reward. The illegal and universally condemned acts of maritime piracy and the legal and nationally praised acts of maritime privateering are the basis for this book. Nearly two hundred legal issues are identified among more than a hundred trials of pirates and prize ships seized by privateers, across several centuries of American and British history. These range from the intention to turn pirate, pirates as witnesses, common versus civil law piracy, trying foreign pirates, and special proofs for convicting women, physician, child, indigent, and Black pirates to the use of letters of marque and reprisals versus privateering commissions, condemning or acquitting neutral ships and cargo, the impact of fraudulent ship's papers, the law of nations versus municipal law, and flying false colors during an attack. For each legal issued identified, the related statutes, crew agreements, ship's papers, and court documents are discussed, starting from the 13th century in Britain, continuing up until the cessation of privateering and the winding down of piracy by the time of the American Civil War. Many figures from the legal history in both countries, judges and lawyers, present their legal reasoning while both better-known and lesser-known pirates and privateers appear as defendants or libelants. From this easy-to-read source with highlighting of key legal points, the reader will gain an understanding of the legal developments behind American law, and its legal ancestor British law, on piracy and privateering. Telling the stories of famous, infamous, and anonymous rogues, rebels, and maritime capitalists from a legal perspective, this book has something for all types of readers: lawyers, judges, law students, fans of history, those interested in pirates and the age of sail, and the general reader.