Captain William Sayle (c. 1590 – 1671) was a prominent English landholder who was Governor of Bermuda in 1643 and again in 1658. As an Independent in religion and politics, and an adherent of Oliver Cromwell, he was dissatisfied with life in Bermuda, and so founded the company of the Eleutheran Adventurers who became the first European settlers of the Bahamas between 1646 and 1648. He later became the first governor of colonial South Carolina from 1670 to 1671.

Bermuda, or the "Somers Isles", was settled by Europeans in 1609 as a result of the wrecking of the Sea Venture, the flagship of the Virginia Company. Although most of the passengers and crew continued to Jamestown, Virginia, the following year on two Bermuda-built ships, the Royal Charter of the company and the boundaries of Virginia were extended to include Bermuda in 1612, when the first governor (at the time, actually the lieutenant-governor) and sixty colonists joined the three men who had remained behind from the Sea Venture. Bermuda's 21 square miles were subdivided into nine parishes (at first called "tribes"). The easternmost, St. George's (where St. George's town was established), was designated "common" or "Crown" land, but the remainder were further subdivided into "shares", each equivalent to a specific share held in the company. The parishes (other than St. George's) were each named for a major shareholder (or "adventurer") in the company. Administration was handed to the crown in 1614, and then in 1615 transferred to a spin-off of the Virginia Company called the Somers Isles Company. The Company appointed a governor, who from 1620 oversaw a House of Assembly that differed from the House of Commons in having no property qualification (due to most land in Bermuda being then owned by absentee landlords). As the House of Assembly consequently governed for the benefit of Bermuda's landless men, a Council made-up of prominent local men appointed by the company was introduced as a combination of upper house and cabinet. This was intended to ensure the balance of power remained with the company, rather than the settlers, but with no other group from which to appoint its members, the council quickly became dominated by men from the same prominent local families that filled the Assembly, and political power rested firmly with this emerging local elite and their descendants until the introduction of universal adult suffrage and party politics in the 1960s.

Although Bermuda quickly became a thriving colony, the growth of tobacco as a cash crop that was the basis of the economy under company administration became unprofitable from the 1620s as Virginia became stable and self-sufficient and England established newer and larger colonies, all of which emulated Bermuda's economy, flooding the English market with cheap tobacco. Few shareholders in the company actually settled in Bermuda, and the land was occupied and worked by tenants and by indentured servants who repaid the cost of their transport to Bermuda with seven years' labour. The more successful settlers (whether they arrived as shareholders or tenants at their own expense or as indentured servants) increased their landholdings by purchasing shares from adventurers who were finding them ever less profitable. Whereas absentee landowners primarily relied on tobacco exports, residents began to switch to maritime trades, replanting the fields that had been cleared from the forest with Bermuda cedar, which was vital to shipbuilding and more valuable than cash crops like tobacco. They also grew food crops and raised livestock for their own consumption, and exported their excess production aboard their new ships for sale in other colonies. This put them at odds with the company, which only earned profits from the tobacco grown for export. This contest between the settlers and the company would end when the settlers took their complaint to the Crown and the company's Royal Charter was revoked in 1684.

Sayle appears to have settled in Bermuda by about 1630. He owned considerable property in the colony, with 165 shares totalling 220.5 acres in Southampton, Smith's, and Pembroke parishes, according to the 1662–1663 survey by Richard Norwood. Among his possessions was the property where the house in Smith's known as Verdmont was built about 1710 off Sayle Road. As one of the colony's most prominent men, he served as a military officer in command of King's Castle, and was at times a member of the council (that combined the roles now performed by the Senate and the Cabinet). By this period, the Somers Isles Company had ceased sending new Governors from abroad, and appointed a succession of prominent residents to the position. Sayle was appointed Governor in 1643, but as an Independent Puritan, aligned with the Parliamentary cause, the Commonwealth and then Oliver Cromwell's Protectorship, he was to be at odds with the majority of Bermuda's dominant elite.

In the 1640s, Bermuda was divided by conflict between the episcopal Church of England and Bermuda's revolutionary Independent Puritans and Presbyterians. This was the same as the conflict between Bermudian Royalists and Parliamentarians, as the English Civil War extended into the English colonies. In Bermuda, most of the settlers had already become estranged from the Somers Isles Company as those shareholders who had remained in England had barred those who lived in Bermuda from having any say in the management of the company. This meant that, although most land was by then owned by residents like Sayle, their interests were thwarted in order to ensure maximum profits for the shareholders in England. As most of the shareholders in England sided with Parliament when war broke out, most Bermudians saw their interests as aligned with the Crown's.

As the Crown and the Church of England attempted to assert their authorities, similar conflicts took place in other parts of the English realm leading up to the Civil War and the Interregnum, as well as in English-ruled Ireland (where native Irish Catholics and royalists would be suppressed after the 1649–1653 Cromwellian conquest of Ireland, and from where Presbyterian settlers from the Kingdom of England and the Kingdom of Scotland, resenting the Crown's attempts in the 1630s to bring them under Episcopalian authority, had begun to re-emigrate to North America where they became known as Scots-Irish or Scotch-Irish).

In Bermuda, at least, the Royalist–Episcopal forces held sway. After Parliamentary victory in England in 1646, five of the financiers of Sayle's mission to Eleuthera signed the death warrant of King Charles I. However, Bermuda, like Virginia and a handful of other colonies, remained loyal to the Crown. Bermuda was the first to recognise Charles II as King following the 1649 execution of his father. Royalists in Bermuda, with control of "the Army" (nine companies of militia infantry and the volunteer artillery that manned the coastal batteries), ousted Captain Thomas Turner, the Company-appointed Governor, in 1649 and elected John Trimingham as their leader. The Commonwealth barred trade with these colonies, which were singled out by the Rump Parliament in An Act for prohibiting Trade with the Barbadoes, Virginia, Bermuda and Antego, which was passed on 30 October 1650. This stated that

due punishment [be] inflicted upon the said Delinquents, do Declare all and every the said persons in Barbada's, Antego, Bermuda's and Virginia, that have contrived, abetted, aided or assisted those horrid Rebellions, or have since willingly joyned with them, to be notorious Robbers and Traitors, and such as by the Law of Nations are not to be permitted any maner of Commerce or Traffique with any people whatsoever; and do forbid to all maner of persons, Foreiners, and others, all maner of Commerce, Traffique and Correspondency whatsoever, to be used or held with the said Rebels in the Barbada's, Bermuda's, Virginia and Antego, or either of them.