This year, America is commemorating the centenary of the death of Samuel Langhorne Clemens (1835-1910), more popularly known as Mark Twain, the 20th century writer who became famous for his works of wit and satire and the characters of his novels, Tom Sawyer and Huckleberry Finn. But there is another side of the famous Mark Twain. This was the Twain of political writing. And, surprisingly, much of it was related to the Philippines at the start of the American occupation. In the last years of his life, Clemens became an activist against American expansionism in Asia and its dire effect – the Philippine-American War. His work with the Anti-Imperialist League attracted much attention and caused some controversies with government officials and his popular audience. This paper traces the history of Twain’s writings against the war and its effect on early American colonial policy in the Philippines. It will also show that at a time when the United States was beginning its empire in the Pacific, not all of the active resistance to the move was confined to our country; much of it was also happening in the land of the new colonial masters.