Acting Governor of Massachusetts
Tailer was elected to the Governor's Council from 1712 to 1729, and was on three separate occasions commissioned as lieutenant governor of Massachusetts. Despite his connection by marriage to the Dudleys, he had an awkward political relationship with the governor during the period of his first two commissions. A number of Anglicans in the colony, Tailer among them, were skeptical of Dudley's faith. (Dudley had been raised in the Puritan way, and had formally adopted Anglican practices while in England in the 1690s.) He and Dudley were also on opposite sides of the debate on the province's currency problems. Dudley favored the issuance of public bills of credit as a means to circumvent the inflationary issuance of paper currency that had become a serious problem by the end of Queen Anne's War in 1713, while Tailer, along with his father-in-law Nathaniel Byfield and others, favored the establishment of a private land bank, that would issue bills secured by the lands of its investors.
Byfield in 1714 went to London to lobby on behalf of the land bank interests, and to seek for himself the post of governor, which was open for consideration after the accession of King George I to the throne. He was unsuccessful in acquiring the governorship, but was able to convince Colonel Elizeus Burges, who had been chosen to replace Dudley, to keep Tailer on as lieutenant governor. Burges, however, was bribed by land bank opponents to resign his post before leaving England. The commissions of Burges and Tailer had by then been sent to Massachusetts, and Tailer became acting governor in November 1715 after they were formally proclaimed.
Immediately after taking office Tailer engaged in political housecleaning, eliminating land bank opponents and Dudley supporters from a number of provincial positions. His efforts, however, backfired: the provincial assembly elected Joseph Dudley's son Paul as attorney general, and London agents of the anti-bank party worked to ensure Tailer's replacement. (One of those agents, Jonathan Belcher, would ironically become a Tailer ally in later years and secure the lieutenant governorship for him the third time.) Through their efforts the king chose Colonel Samuel Shute, a land bank opponent, to replace Burges, and William Dummer as Shute's lieutenant governor. Tailer was turned out of office with Shute's arrival in October 1716. Shute deliberately snubbed Tailer upon his arrival, choosing to first meet with the Dudleys instead.
The only major long-term accomplishment of Tailer's tenure as acting governor was the establishment of Boston Light, the first lighthouse built in what is now the United States. While a member of the assembly, Tailer had sat on the legislative committee that drafted the enabling and funding bills, and he signed them after he became governor.
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