This paper explores the life and activities of Hugh Hamilton Lindsay (1802–81), an East India Company official who worked at Canton from 1820. Lindsay's is a key voice in the challenge to the Company's policies in China on the cusp of the abolition of its monopoly, and to British policy on the eve of the first ‘Opium War’ with the empire of the Qing. Lindsay first made his mark on Sino-British relations by leading a covert East India Company foray north along the Chinese coast in 1832 in the ship Lord Amherst, and in widely disseminating his bullish conclusions and policy recommendations in publications and reports that followed. He is known as a bellicose pamphleteer, but a more complex picture emerges if we follow Lindsay and his commercial activities as the British fanned out from Canton into the Chinese ‘treaty ports’ opened after 1842, and across Britain's wider developing empire in Asia. His field of operations developed to include the British colony of Labuan and led him into a heated public conflict with Sir James Brooke in the early 1850s. Lindsay was never happy with the status quo: he lobbied and hectored, and in business he innovated, and pushed hard on the frontiers of British power and influence. Commercial opportunity drove him, but so did a specific vision of the ‘English character’, and notions of pride and national and personal honour.