Pickler was a Republican politician. He moved to the Dakota Territory and served in the territorial legislature in 1884. While serving in the Dakota Legislature, he played a key role in introducing the territory's first bill to give women the right to vote. After South Dakota was admitted as a state, he was elected as a Republican to Seat A, one of South Dakota's at-large seats in the United States House of Representatives. He was reelected in 1890, 1892, and 1894, and served from November 2, 1889 to March 3, 1897. On Whiting watermark Paper