He also ran for U.S. House of Representatives five times on the Socialist or Social Democratic ticket, and was a candidate for Governor of Wisconsin in 1906.

In 1904, he was nominated for U.S. House of Representatives from Wisconsin's 4th congressional district, losing to Republican incumbent Theobald Otjen.

[5] In 1910, he was again the Socialist nominee for the 4th congressional district, coming in a close second to Democratic incumbent William Joseph Cary.

[10] In May 1917, Gaylord and A. M. Simons wrote a letter to U.S. senator Paul Husting denouncing him as a traitor to the anti-World War I majority of the Socialist convention in April 1917 and recommending his suppression from the government, claimed a communication published in the Congressional Record.

[12] 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.