He was a political opponent of Governor Joseph Dudley, and was a supporter of a land bank proposal intended to address the province's currency problems.

He was active in the provincial defense, and commanded a regiment in the 1710 siege of Port Royal, the capital of French Acadia, during Queen Anne's War.

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.

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.

[8][15] 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.

[8][16] 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.

[8] 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.

[21] 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.

He successfully convinced Lord Cobham that he deserved one for his service at Port Royal in 1710, and was awarded the half pay of a colonel, amounting to £400 per year.

Under Shute's governorship he was several times involved in negotiations with Indians on the northern frontiers,[25] and continued to be active in the provincial militia.

Although a potential basis for agreement was identified, continued raiding and disagreement on the details of proposed terms caused the situation to deteriorate further.

Tailer was one of the lead members of a party sent in 1723 to Albany, New York in an attempt to convince the Iroquois to join the conflict against the Abenaki.