 Later that year, Howe was hired by Thomas Mott Osborne, a rich Democrat, as a political operative.Osborne was a member of the "Upstarters", a group opposed to the influence of the Tammany Hall political machine in New York politics.He employed Howe to oppose the gubernatorial candidacy of William Randolph Hearst, the Democratic nominee, newspaper magnate, and ally of Tammany.