In addition to service as a militia officer during the American Revolution, he served as a county judge and sheriff, member of both houses of the Massachusetts legislature, U.S.
He served for two years as Treasurer and Receiver-General of Massachusetts, and after his death an audit showed his accounts to be deficient for more than the value of his estate, which led to those who had posted bonds on his behalf having to pay the debt.
[2] At age 21 Skinner moved to Williamstown, Massachusetts with his brother, where they went into the construction business as partners in a firm they named "T. J. and B.
In the summer of 1776 he carried messages between units in Berkshire County and General Horatio Gates, commander of the Continental Army's Northern Department in upstate New York.
[23] Skinner represented Massachusetts's 1st congressional district (Berkshire County) in the U.S. House for part of one term and all of another, January 1797 to March 1799.
[27] Skinner, by now identified with the Jeffersonian or Democratic-Republican Party, lost to John Quincy Adams, the Federalist candidate, in an 1803 election for U.S.
Several of the individuals who had posted surety bonds to guarantee his performance as treasurer paid portions of the remaining $40,000 obligation in order to satisfy Skinner's debt.