Sir William Courteen took on the East India Company — the monopoly outlasted him

Sir William Courteen (1572–1636) was one of London's wealthiest merchants. For three decades he built a trading network spanning Guinea, Portugal, Spain and the West Indies, operating a fleet of 20 ships crewed by nearly 5,000 sailors. His firm dealt in silk, linen, and colonial goods, and by 1631 his capital was estimated at £150,000 — a fortune at the time.

Courteen's ambitions grew beyond his base. He had discovered and begun colonising Barbados around 1624, shipping 1,850 settlers there, but lost the island to the Earl of Carlisle in 1629 after a disputed grant. Then, spurred by losses to Dutch privateers in the East Indies and resentful of the East India Company's monopoly, he secured a royal trading licence in 1635 — the Courteen Association — to trade with Asia in any territory the EIC did not occupy. He dispatched two ships to China, the Dragon and the Katherine, with an embassy to open trade. The ships never arrived.

Courteen died in May or June 1636, immediately after the fleet sailed. Without his leadership, the venture unravelled. Barbary pirates seized one ship. Dutch and Portuguese vessels harassed the rest. Malaria devastated the crews. Embassies were rebuffed in Madagascar, India and Macau. Only three of six vessels returned. Courteen's son, also William, inherited an estate already tangled in litigation — including £200,000 in unpaid royal loans — and went bankrupt in 1643. He fled to Italy and died intestate in Florence in 1655.

The Courteen Association collapsed, but its remnants — its surviving capital, its experienced personnel, its idea of a rival to the EIC — were absorbed by Maurice Thompson's Assada Adventurers. After years of struggle, Cromwell forced a merger that produced a new, stronger East India Company in 1657, capitalised at £739,782. The company that Courteen set out to challenge outlasted his challenge and emerged more dominant than before.