Acknowledging that the external context visibly affects any organization, this investigation seeks to constitute a specific contribution to the study of the importance of public image in organizational administration. To that end, a collection and documentary analysis of news stories from the newspaper O Fayalense on the Asylum for the Disadvantaged Children of Horta [Asilo de Infância Desvalida da Horta], an institution located on Faial Island, Azores, Portugal, covering the time period of 1858 to 1895, is performed. In the presentation and discussion of the results, a comparison is made between two periods that involve a single president because they vary in the type of news stories published (at the level of sources and subjects). It is concluded that the news stories published cover three large types of references, which, given the period in question, vary substantially: factual information (on the celebrations occurring in the asylum, communications about donations received and appreciation of benefactors, or institutional information on the elections of the asylum directorate), praise (regarding the asylum’s mission, operation, or administration), and censures (including responses to external criticism, criticism of previous managements, and stories regarding the asylum’s precarious circumstances). The implication of the study is that the importance of a positive public image, especially a positive image that is supportive of the leadership, should not be overlooked for the organizational administration to have greater chances of success.