 Howe was then was assigned to cover the New York state legislature in 1906, and soon became a political operative for Thomas Mott Osborne, a Democratic opponent of the Tammany Hall political machine.After Osborne fired Howe in 1909, Howe attached himself to rising Democratic star Franklin D. Roosevelt, with whom he would work for the rest of his life.Howe oversaw Roosevelt's campaign for the New York State Senate, worked with him in the Navy Department, and acted as an advisor and campaign manager during Roosevelt's 1920 vice presidential run.