Hale was a member of the
Boston Board of Aldermen from 1908 until it was replaced by the new
Boston City Council in 1909. He served on the new city council from 1909 to 1911. In June 1912, the group combined with Arthur L. Nason's Militant Progressive League of Massachusetts to form the Progressive Party of Massachusetts. Hale was elected chairman of the new party. He was elected to the Progressive National Committee in 1913 and managed
Charles Sumner Bird's campaign in the
1913 Massachusetts gubernatorial election. He endorsed the party's nominee, Nelson B. Clark, but did not play an active role in the campaign. At the
1916 Progressive National Convention, Hale was chosen to be vice chairman of the Progressive National Committee. After
Theodore Roosevelt refused the party's nomination, the national committee voted to endorse the
Republican nominee
Charles Evans Hughes. Hale opposed this decision and campaigned for the Democratic candidate,
Woodrow Wilson. At the 1917 Progressive national convention, the delegates voted to remove the National committee that endorsed Hughes and chose Hale to serve as national chairman. That October, he attended the orgnizational meeting of the
National Party, which was formed by pro-war members of the Progressive Party,
Socialist Party of America,
Single Tax Party,
Farmers' Alliance, and
independents. Hale was elected as a delegate-at-large to the Massachusetts Constitutional Convention of 1917–1918 as a member of the Progressive Party. In 1917, Democratic Party leaders chose Hale to be the party's candidate for Lieutenant Governor. Hale accepted the Democratic nomination, but did not leave the Progressive Party. He appeared on the ballot as the Democratic, Progressive, and
Prohibition Party candidate and received 121,426 votes to Republican
Calvin Coolidge's 223,157. During
World War I, President Wilson appointed Hale to be one of ten umpires to hear labor cases on which the
National War Labor Board could not reach and agreement. ==Business interests==