A profligate son was every Georgian parent’s worst nightmare. To his father, William Jackson’s imprudent spending, incessant partying, and sexual adventures were a sure sign he was on the slippery slope to ruin. But to his friends, William was a “damned good fellow,” a charming, impeccably dressed young gentleman with enviable seductive skills who was willing to defend his honor in duels. Mr. Jackson and his son viewed each other across a generational gap that neither could bridge, and their flawed relationship had catastrophic consequences for their family.

In The Profligate Son, historian Nicola Phillips hauntingly reconstructs this family tragedy from a recently discovered trove of letters and court documents. After Mr. Jackson’s acquisition of a fortune during his service for the East India Company in Madras was undermined by false accusations that ruined his career, he invested all his future ambitions in his only son. William grew up in great comfort and was sent to the best schools in the country. But when the family moved to London, the teenager rebelled against the loneliness and often brutal regimes of public schooling and escaped to explore the pleasures of the town with his wealthy friends. His attempts to impress his peers led him into disastrous levels of debt that resulted in his imprisonment and ever more illegal efforts to satisfy his creditors, which appalled his prudent, sternly moralistic father. Mr. Jackson decided that the only way to combat his son’s wayward behavior was to completely cut him off. In doing so, he condemned William to repeated imprisonment and a perilous voyage to an Australian penal colony. In Sydney William sought to rebuild his life with a family of his own, but even there his father’s legacy brought further tragedy.

A masterpiece of literary nonfiction as dramatic as any Dickens novel, The Profligate Son transports readers from the steamy streets of India and the elegant squares and seedy brothels of London to the sunbaked shores of Australia, tracing the arc of a life long buried in history.