Grupo Prisa has been the leading media group in Spain for more than 30 years. During this time it has expanded its activities from a single newspaper publisher to a crossmedia conglomerate with leading positions in the press, radio, pay television, and publishing segments in Spain as well as internationally. In the last decade, the group has also seen its nature, structure, and ownership deeply challenged and radically transformed. This article describes this process and contextualizes and documents the reasons for Grupo Prisa’s rise and success until 2010, as well as the corporate financial crisis that threatened its nature and profile as a reference news media producer. Finally, some general lessons extracted from this case study are provided.