The story of the first attempt to construct a tall building in Valparaíso after the 1906 earthquake allows us to understand the technical and construction possibilities and limitations of the time, as well as the actions taken in response to a series of conflicts between the architect, the client, the municipality, and the media. Valparaíso was one of the main ports of the American Pacific between the middle of the 19th century and the first quarter of the 20th century, concentrating the investment of the profits obtained from mining in the north and south of Chile. The building designed by the engineer and architect Joaquin Barella was commissioned by the mining entrepreneur Francisco Caralps. The nine-storey building was originally designed as a metal structure embedded in concrete. The project went through a series of stages with transformations in its relationship to the ground and the hill, as well as its interior layout. The comparative description of the buildings designed by Barella in the period, the reconstruction of each of the stages of the project, the analysis of the discussion in the media related to the incidents during the construction of the building and the understanding of the life of Francisco Caralps allow us to build a finished panorama of the failed attempt to build a skyscraper in Valparaíso.