In 1897-1898 secret agents from the Pinkerton National Detective Agency were following American war correspondents in Havana, Cuba. These agents were all Americans yet they all seemingly had a common employer: the Spanish diplomatic minister in the United States. The mission of the operatives that were sent to Cuba was to inform, as well as to sabotage, the journalist work of these correspondents who kept feeding the animosity of American public opinion against Spain. They also sought to identify other spies who were helping the Cubans as well as the Americans. In this mélange of (private) espionage and (public) published stories, who were the ‘real’ spies and for whom did they really work for? According to the detective reports, what was going on and what stories were being told about the war in Cuba by these American journalists? This brown bag presentation will discuss what we have learned so far from this research as well as how the tools provided by digital humanities were used to uncover spies, the crafting of narratives, and the relationships among them through time.