Squires was a Republican. He was elected to the Wisconsin State Assembly in 1942 and 1948. In addition to serving in the Assembly, he was town chairman of Mason, Wisconsin and of the Bayfield County, Wisconsin Board.
During his career as an assemblyman, he was a member of a group of northern Wisconsin legislators known as the "Woodchoppers," who favored reintroducing bounties on wolves and other predators.