Early Life and Military Service
William Tailer was born in Dorchester, Massachusetts Bay Colony on February 25, 1675/6 to William Tailer and Rebecca Stoughton Tailer. His mother was the daughter of early Massachusetts settler Israel Stoughton and sister to magistrate William Stoughton. His father was a wealthy landowner and merchant. His father owned commercial real estate in Boston and was a member of the Atherton Company, one of New England's most powerful and well-connected land development partnerships. He was also one of "a selected fraternity" of merchants engaged in the "eastward trade" with neighboring French Acadia, one of whose leading members was Boston merchant John Nelson. Tailer's father committed suicide in 1682, apparently suffering from depression which may have been brought on by financial reverses.
The younger Tailer inherited a substantial estate; it was reported that in 1695 his guardians operated five mills on his behalf. He was also a beneficiary of the large estate of his uncle, who died a childless bachelor. By 1702 Tailer had married Sarah Byfield, daughter to Nathaniel Byfield, another leading colonial magistrate. She died childless in about 1708. Byfield and Tailer's father had been business partners, a relationship that Tailer continued.
Tailer was a captain of the Ancient and Honorable Artillery Company, and served in the provincial militia during Queen Anne's War. In 1710 he commanded a militia regiment that saw action at the capture of Port Royal, Acadia. Following the victory he went London with Francis Nicholson, the expedition's leader, where he was "bigg with expectation" of advancement. His expectations were rewarded with a commission as lieutenant governor of the Province of Massachusetts Bay, serving under Governor Joseph Dudley. He then returned to Massachusetts, where he was again active in the defense of the colonies, serving at Fort William and Mary in New Hampshire, and reporting on the frontier defenses in what is now southern Maine (but was then part of Massachusetts). In early 1711/2 he married Abigail Gillam Dudley, widow of Joseph Dudley's grandson Thomas. The couple had six children, who they raised in the old Stoughton homestead in Dorchester.
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