Much debate traditionally surrounds the concept of the bill of lading as a document of title. What does the word ‘title’ mean, and is the concept of title linked to the possession of the goods? And how does the endorsement of a bill of lading transfer the right to delivery of the goods to its lawful holder? Is the notion of lawful holder of a bill of lading just an ancillary element, or does it have a role to play in terms of defining the legal connotations of the concept of a bill of lading as a document of title? This chapter endeavours to provide an answer to the aforementioned questions, in the quest for the identification of the legal traits of the bill of lading as a document of title. This will be done by embarking upon an historical journey which will put emphasis on Roman law, as well as on the common law traditional ‘struggle’ to legally conceptualise the concept of ‘document of title’.