In 1669, fleeing a London decimated by the plague and the Great Fire, a young English child arrived, alone, at Fort St. George, the first English fortress in Mughal India. The boy survived to become a maverick merchant-mariner, an ‘independent’ trading on the fringes of the East India Company. Captain Thomas Bowrey gained renown in numerous fields. Operating throughout the East Indies and speaking Malay, the lingua franca of diplomacy and trade in the region, he would write and publish the first ever Malay-English dictionary, a seminal work that even a century later would be used by the likes of Thomas Stamford Raffles, the founder of Singapore. It has also been claimed Bowrey wrote the earliest first-hand account of the recreational use of cannabis. Bowrey’s shipping interests, however, were plagued by pirates, privateers and mutiny and included the tragic Worcester, which played a pivotal role in the union of England and Scotland. Subsequent projects included the east African slave trade and his collaboration with Daniel Defoe in the founding of the South Sea Company. Despite everything, Bowrey succeeded in amassing sufficient fortune for alms-houses to be built in his name following his death, but his true legacy is his papers that lay hidden in an attic for two centuries and which now shed light not only on the exploits of this remarkable man but also on life and commerce at the start of globalisation.