In Regency England a profligate son was regarded as every parent's worst nightmare: he symbolized the dangerous temptations of a new consumer society and the failure of parents to instil moral, sexual, and financial self-control in their sons. This book tells the dramatic and moving story of one of those 'profligate sons': William Jackson, a charming teenage boy, whose embattled relationship with his father and frustrated attempts to keep up with his wealthy friends, resulted in personal and family tragedy. From popular public school boy to the pursuit of prostitutes, from duelling to debtors' prison and finally, from fraudster to convicted felon awaiting transportation to Australia, William's father (a wealthy East India Company merchant) chronicled every step of his son's descent into depravity and crime. This remarkable source provides a unique and compelling insight into the relationship between a father and son at a time when the gap between different generations yawned particularly wide. Diving beneath the polished elegance of Britain in Byron's 'age of surfaces', the tragic tale of William Jackson reveals the murky underworld of debt, disease, crime, pornography, and prostitution that lay so close beneath the veneer of 'polite society'. In a last flowering of exuberant eighteenth-century hedonism before the dawning of Victorian respectability, young William became disastrously familiar with them all. The Profligate Son combines a gripping tale with cutting-edge historical research into early nineteenth-century family conflict, attitudes towards sexuality, credit, and debt, and the brutal criminal justice system in Britain and Australia at the time. It also offers challenging analogies to modern concerns by revealing what Georgians believed to be the best way to raise young men, what they considered to be the relative responsibilities of parents and children, and how they dealt with the problems of debt during the first age of mass consumer credit.