Woodes Rogers was the eldest son and heir of Woods Rogers, a successful merchant captain. Woodes Rogers spent part of his childhood in Poole, England, where he likely attended the local school; his father, who owned shares in many ships, was often away nine months of the year with the Newfoundland fishing fleet. Sometime between 1690 and 1696, Captain Rogers moved his family to Bristol. In November 1697, Woodes Rogers was apprenticed to Bristol mariner John Yeamans, to learn the profession of a sailor.

Rogers encountered financial problems on his return. Sir William Whetstone had died, and Rogers, having failed to recoup his business losses through privateering, was forced to sell his Bristol home to support his family. He was successfully sued by a group of over 200 of his crew, who stated that they had not received their fair share of the expedition profits. The profits from his book were not enough to overcome these setbacks, and he was forced into bankruptcy. His wife gave birth to their fourth child a year after his return--a boy who died in infancy--and Woodes and Sarah Rogers soon permanently separated.  Rogers decided the way out of his financial difficulty was to lead another expedition, this time against pirates. In 1713, Rogers led what was ostensibly an expedition to purchase slaves in Madagascar and take them to the Dutch East Indies, this time with the permission of the British East India Company. However, Rogers' secondary purpose was to gather details on the pirates of Madagascar, hoping to destroy or reform them, and colonise Madagascar on a future trip. Rogers collected information regarding pirates and their vessels near the island. Finding that a large number of the pirates had gone native, he persuaded many of them to sign a petition to Queen Anne asking her for clemency. While Rogers' expedition was profitable, when it returned to London in 1715, the British East India Company vetoed the idea of a colonial expedition to Madagascar, believing a colony was a greater threat to its monopoly than a few pirates. Accordingly, Rogers turned his sights from Madagascar to the West Indies. His connections included several of the advisers to the new king, George I, who had succeeded Queen Anne in 1714, and Rogers was able to forge an agreement for a company to manage the Bahamas, which were infested with pirates, in exchange for a share of the colony's profits.  At the time, according to the Governor of Bermuda, the Bahamas were "without any face or form of Government" and the colony was a "sink or nest of infamous rascals". Until Rogers obtained his commission, the islands had been nominally governed by absentee Lords Proprietor, who did little except appoint a new, powerless governor when the position fell vacant. Under the agreement that underlaid Rogers' commission, the Lords Proprietor leased their rights for a token sum to Rogers' company for twenty-one years.  On 5 January 1718, a proclamation was issued announcing clemency for all piratical offences, provided that those seeking what became known as the "King's Pardon" surrendered not later than 5 September 1718. Colonial governors and deputy governors were authorised to grant the pardon. Rogers was officially appointed "Captain General and Governor in Chief" by George I on 6 January 1718. He did not leave immediately for his new bailiwick, but spent several months preparing the expedition, which included seven ships, 100 soldiers, 130 colonists, and supplies ranging from food for the expedition members and ships' crews to religious pamphlets to give to the pirates, whom Rogers believed would respond to spiritual teachings. On 22 April 1718, the expedition, accompanied by three Royal Navy vessels, sailed out of the Thames.

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did he ever resolve his financial difficulties?