This essay traces the lost life of Derwent Moultrie Coleridge – Derwent Coleridge’s eldest son, S. T. Coleridge’s first grandson – who was exiled to Australia in 1850. Through analysis of family correspondence, I explore the history which led to Derwent Moultrie’s exile, which was deemed to be the only “solution” to his drinking habits and reckless behaviour. There is a striking parallel between the lives of Derwent Moultrie and his uncle Hartley. I argue that Derwent’s conflicted relationship with his brother Hartley (and with his father) conditioned his strict treatment of his son. And, in turn, that Derwent’s disappointment with his son influenced his somewhat disjunctive representation of Hartley in his influential Memoir of his brother (1851), which shaped Hartley’s posthumous reputation. Finally, this essay shows how, despite a life of turbulent hardship in Australia, Derwent Moultrie contributed to the growth of Australian literature, a notable achievement which is yet to be critically recognised.