Reprise As Acting Governor
Tailer's politics shifted during the 1720s, and he and Byfield came to align more closely with the populist faction. As a result he and one-time opponent Jonathan Belcher became allies. When Governor William Burnet died in 1729, Belcher was in London, acting as agent for Connecticut and assisting in lobbying against Burnet's unpopular insistence on a permanent salary. Belcher successfully gained for himself the post of governor, and then secured for Tailer another appointment as lieutenant governor. Tailer's commission was proclaimed before Belcher's arrival, and he briefly served as acting governor while awaiting his superior's arrival. The few months were uneventful, as the province was then suffering from an outbreak of smallpox, because of which Tailer prorogued the assembly.
Tailer died in Dorchester, while serving as lieutenant governor, in March 1731/2. His pallbearers included Governor Belcher and other leading political figures. He is buried in the tomb of his uncle, Willam Stoughton, in what is now called the Dorchester North Burying Ground.
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