 In 1785, he was one of the founders of the New Brunswick bar and set up practice in Saint John.Chipman's clients included Benedict Arnold.Also in 1785, he ran as a pro-government candidate for the Legislative Assembly and was elected, although he is said to have the support of the local sheriff in the inspection of the ballots; he was defeated in the 1793 election for the 2nd New Brunswick Legislature, but returned in Northumberland County.