Cleveland's presidential inauguration as he was afraid that Secretary of State Amos W. Barber would appoint a Republican during the time that he would server as acting governor in Osborne's absence. During his tenure he fought with the state legislature which was divided with 22 Republicans, 21 Democrats, and 5 Populists. He completed his term on January 7, 1895, having declined renomination. From March 4, 1897 until March 3, 1899, he served in the 55th United States Congress as the U.S. representative from Wyoming, but again declined renomination when his term expired. Later life Osborne was a free silver supporter and during the 1896, 1900, and 1908 presidential elections he supported William Jennings Bryan. In 1896 he served as chairman of the Wyoming delegation to the Democratic National Convention, in 1898 he served as vice chairman of the Democratic National Committee, was made a member of the national committee in 1900, and served as the vice chairman of the finance committee in 1908. During the 1904 presidential election Bryan suggested that somebody like Osborne from the western United States should run for the Democratic nomination, but Osborne chose not to run. On April 28, 1903, Governor DeForest Richards died in office shortly after winning reelection in 1902 resulting in a special election. Osborne won the Democratic nomination by acclamation, but was defeated in a landslide in the special election by Bryant Butler Brooks. On November 2, 1907, he married Selina Smith of Princeton, Kentucky after they met on the island of Madeira when Jean Curtis Smith was on a round-the-world trip with her sister and brother-in-law. According to an account in the Passenger-Inquirer of Owensboro, Kentucky, "they were engaged to be married when they landed on American soil two months later." Their honeymoon was interrupted "when his efforts to secure the 1908 Democratic National Convention for the West met with success and they were obliged to hurry to [Denver," where it was to be held. Mrs. Osborne was known as the "official hostess" for the convention. In 1910, he served as chairman of the Wyoming Democratic Party. Osborne was appointed Assistant Secretary of State by President Woodrow Wilson and served in his administration from April 21, 1913 until December 14, 1915. He was also chairman of the board of the Rawlins National Bank, and engaged in stock raising. In 1913, he suggested that the remains of Christopher Columbus should be