1875: Founding member and secretary of the Brotherhood of Locomotive Firemen
1880: Grand Secretary of the Brotherhood of Locomotive Firemen
1884: Indiana General Assembly, served as a democrat
1893: Founded the American Railway Union (one of the first industrial unions in America)
1894: Arrested for allegedly obstructing U.S. mail
1900: Ran for President and Congress as a Socialist
1901: Chairman of the Executive Board of the National Council of the Socialist Democratic Party of the United States
1904: Ran as the Socialist Party of America candidate for President
1905: Founded the Industrial Workers of the World (labor union)
1908: Ran as the Socialist Party of America candidate for President
1912: Ran as the Socialist Party of America candidate for President
1919: Imprisoned on 10 counts of sedition
1920: Ran as the Socialist Party of America candidate for President