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.