Cheney also became active in the insurance business, and was president of the Vermont Insurance Federation and a director of the Vermont Mutual Fire Insurance Company.[4][5]
A Republican, in 1892 Cheney worked in the office of the Vermont Secretary of State. He was an assistant clerk of the Vermont House of Representatives from 1894 to 1898, and clerk from 1898 to 1906.[6]
In 1906 and 1908, Cheney was elected as a member of the Vermont House, serving from 1906 to 1910. He was Speaker for the entire length of his house service.[8]
After leaving office, Cheney returned to his legal and insurance interests. He died in Morrisville on October 13, 1957, and was buried in the Pleasant View Cemetery there.[9]