In 1836, young Gordon opened a store in Kingston and operated as a produce dealer.
Richard Hill, a mixed-race lawyer and leader of the free coloured community, met him in that year and said of him, "He impressed me then, though young-looking, with the air of a man of ready business habits." Gordon was a successful businessman. In 1842, he had earned enough to be able to send his sisters to England and France to be educated. Three years later, he was worth £10,000. His father had little to do with him when he was growing up, but when Joseph ran into financial difficulties, it was the son who bailed him out, and cleared the debts on Cherry Garden, before giving it back to the father. Gordon later moved to
St. Thomas-in-the-East Parish at the eastern end of the island, where he became a wealthy businessman and a landowner. In the 1840s, he co-founded the Jamaica Mutual Life Assurance Society, and was appointed a justice of the peace in seven parishes. Gordon was a radical politician who was popular in the parish of St. Thomas-in-the-East, and he was deeply affected by the suffering of the black poor. He complained to a previous governor,
Charles Henry Darling, about the poor conditions of the Morant Bay gaol. In 1862, when he made similar complaints to Eyre, the governor immediately removed Gordon from the magistracy. The
Colonial Office took the curious stance of backing Eyre while praising Gordon for calling for prison conditions to be improved. Gordon earned a reputation by the mid-1860s as a critic of the colonial government, especially Governor
Edward John Eyre. He maintained a correspondence with English evangelical critics of colonial policy. He also established a Native Baptist church, where
Paul Bogle was a deacon. In 1863, Gordon defeated his rival, a white planter, for a seat on the Assembly for St Thomas-in-the-East with the support of the small settler vote, galvanised by Bogle. Gordon was also made a member of the parish
vestry. However, the colonial elite who ran the parish vestry objected to the presence of Gordon, because he represented the concerns of the black peasantry. A father and son team of the same name, Stephen Cooke, conspired to have Gordon expelled from the parish vestry, a move that angered the black peasantry. The next year, the settlers re-elected Gordon to the parish vestry, and he brought a court action against the
custos of the parish, Baron von Ketelhodt. In May 1865 Gordon allegedly attempted to purchase an ex-Confederate schooner with a view to ferrying arms and ammunition to Jamaica from the United States of America, although this was unknown at the time. In 1865 the mass of Jamaicans were ex-slaves and their descendants; they struggled with poverty and crop failure in the mostly rural economy, and the aftermath of crippling epidemics of
cholera and
smallpox. Gordon criticised Eyre's draconian punishments such as flogging and the
treadmill for crimes such as stealing food. He warned "If that we are to be governed by such a Governor much longer, the people will have to fly to arms and become self-governing." ==Morant Bay Rebellion==