Henry Hawley was the controversial English Governor of Barbados from 1630 to 1640.
Henry Hawley was the younger son of James Hawley, who held the lease for Brentford Market in Middlesex and, until 1622, the lease for Boston Manor nearby. His father was a Mercer who had trained at Middle Temple, one of the Inns of Court to do with Law in London but does not appear to have been called to the bar. Governor Henry Hawley himself served a Mercer's apprenticeship at the Three Cranes Tavern in London. Almost all of Governor Henry Hawley's siblings embarked on colonisation in the New World. One exception was his younger brother, Gabriel, who left his Draper's apprenticeship to serve in 1622 his Mercer uncle Henry Hawley, who had been newly appointed as the English East India Company's chief merchant in the East Indies. Governor Henry Hawley's brother, James, had served his Mercer's apprenticeship with his uncle Henry Hawley and may have immigrated to settle in Virginia. Governor Henry Hawley appointed his brother, William to colonise and govern St. Croix, one of the Virgin Islands but they were soon routed by the Spanish. Governor Henry Hawley's sister, Susan, married Richard Peers, a fellow planter and in Hawley's absence, the acting deputy governor. In addition, he was also brother in law of Richard Ashcraft (1590-1600). Governor Henry Hawley's eldest brother, Jerome, was one of eight investors in the founding of Maryland colony and served in the colony's General Assembley. As Captain Henry Hawley, he was appointed governor of Barbados in 1630, arriving in June that year initially in the capacity of Commissioner to the Earl of Carlisle, who after a war of patents between himself, Sir William Courten and the Duke of Marlborough, emerged as the victorious proprietor of the island. James Hay, the Earl of Carlisle, a favourite of King James I and a fellow Scot, died heavily in debt in 1636 and, owing to the minority of his son, trustees were appointed to administer his estate. Onerous demands were made on Barbados by the trustees to settle these debts via high taxes (payable in cotton or tobacco) and custom duties. The high taxes and tariffs, brutally enforced by the governor, proved to be arduous to the islanders and injurious to trade.