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When the British government abolished slavery in the Caribbean and compensated the slave-owners, some of the beneficiaries and/or their children and grandchildren went to Australia to make a new life and if possible a new fortune. This essay traces the history of one such family, the Shiells of Montserrat, alongside two other contemporaneous histories – that of Yorkshire radical and convict, John Burkinshaw, and his family, into which one of the Shiells married, and that of the several Indigenous communities these families encountered. Through the experiences of these disparate and intersecting family groups, we can gain insight into both the lived experience and the wider imperial context of the expansion of Australian settler colonialism.