He served as National Lecturer for the Socialist Party and as a member of the state executive board. In 1904, he was nominated for Congress from the Fourth District, losing to Republican incumbent Theobald Otjen. In 1906, he was the Socialist nominee for Governor of Wisconsin, losing to Republican acting Governor James O. Davidson, coming in third in a five-way race. He was a delegate to the Milwaukee city charter convention of 1908, and his translation of Changes in the theory and tactics of the social-democracy by Paul Kampffmeyer was published by Charles H Kerr Company Publishers that same year.
Legislative service
Gaylord was elected in November 1908 to the State Senate from the Sixth district for a four-year term to succeed fellow Socialist Jacob Rummel, receiving 6,236 votes against 5,820 for Republican August Langhoff. He was appointed to the standing committees on manufactures and labor, and on public health. In 1910, he was again the Socialist nominee for the Fourth Congressional District, coming in second to Democratic incumbent William Joseph Cary, and in that banner election year for the Socialist Party of Milwaukee came with 447 votes of unseating the incumbent. By 1911, he was the statewide Organizer for the Socialist Party. In 1912, with his Senate district had been redistricted out of existence, he was again the Socialist nominee for the Fourth Congressional District, coming in second again to William Joseph Cary. He was also serving as Chairman of the Socialist Party's statewide executive committee. In 1914 he was the Congressional candidate, and came within 365 votes of unseating Cary. In 1916, he still came in second and received almost one-third of the vote, but Cary extended his winning margin over Gaylord to almost one thousand votes.
Influence and controversy
Gaylord was credited by Carl Sandburg with introducing him to the ideas of the Wisconsin wing of the Socialist Party, and with persuading him to move to Wisconsin. In May 1917 Gaylord and A.M. Simons wrote a letter to Senate of the United StatesPaul Husting denouncing as treasonable the anti-World War I majority report of the Socialist convention in April 1917 and recommending its suppression by the government, a communication published in the Congressional Record. Husting used this letter and additional communications from Gaylord to the Milwaukee Journal in support of the Espionage Act of 1917. As a result, the Milwaukee Central Committee of the Socialist Party took action against both Gaylord and Simons, expelling them for "Party Treason" by a vote of 63 to 2. He became a leading member of the pro-war element within the labor movement in the United States, speaking on platforms with such conservative icons as Nicholas Murray Butler. He was among those who were present at the September, 1917 organizing meeting of the Wisconsin Loyalty Legion. Gaylord died in Palmetto, Florida on February 23, 1943. His wife, Olive Semarimus Brown Gaylord, died nine years later.
