John Piper came to Australia with the NSW Corps in 1792, rising to the rank of Captain. In 1814, he took up the civil service position of Naval Officer for Sydney Harbour, responsible for the collection of customs duties. This role allowed him to accumulate a large amount of wealth. Piper’s lifestyle quickly took on an unprecedented extravagance until he was declared bankrupt in 1827.

This life-size portrait was commissioned to assert Piper’s prominence in Sydney society; only the Governor of NSW, Sir Thomas Brisbane, had his portrait painted on such a large scale. Piper is posed in a uniform of his own design, with the view behind looking towards Point Piper and Henrietta Villa, the grand mansion he built there in 1822, at a cost of £10,000.