Provincial Military Service
He next traveled to England. There he lobbied, on behalf of John Nelson, heir to Sir Thomas Temple's claims to Nova Scotia. Nelson sought recompense for the loss of the territory in the 1667 Treaty of Breda, but Tailer's efforts were in vain. He also lobbied on his own behalf for a military pension. 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. John Nelson observed that Tailer's loss of the lieutenant governorship (worth £50 per year) "has proved much to his advantage".
Tailer eventually returned to Massachusetts. Under Shute's governorship he was several times involved in negotiations with Indians on the northern frontiers, and continued to be active in the provincial militia. Tailer accompanied Shute on an expedition to Maine to negotiate with the Abenaki of northern New England in 1717. Shute handled the negotiations poorly, raising tensions between the Abenaki and British settlers. In 1720 Tailer was one of several commissioners sent to mediate between the settlers and Abenaki. Although a potential basis for agreement was identified, continued raiding and disagreement on the details of proposed terms caused the situation to deteriorate further. Shute declared war on the Abenaki in July 1722 following raids against British settlements on the Maine coast.
Shute's ongoing conflicts with the provincial assembly prompted him to leave for England in early 1723, leaving handling of the war in Lieutenant Governor Dummer's hands. 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. The embassy was unsuccessful: the Iroquois resisted all attempts to bring them into the war against the Abenaki. Tailer continued to be involved in the war, where he was responsible for maintaining Boston's defenses.
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