This article tells the story of how the journalistic practices of David Hamilton Jackson (1884–1946), a local of St. Croix, in the newspaper The Herald (1915–1925) produced cultural and cosmopolitan bridges in (post)colonial times and how these connections were built on cultural and journalistic practices rather than on technological advancements. Based on a critical, discursive reading of The Herald, the article argues that despite the dominant narrative of the telegraph’s cosmopolitan qualities, which is supported by its perceived neutral transmission of news between peoples and cultures, the telegraph’s neutrality, like journalism’s own ambition of objectivity, is contestable. Rather, when looking for cosmopolitan connections – understood as worldwide, cultural citizenship – and citizen journalism, the reader is urged to consider the embodied, political acts and engagements of subjects struggling to gain rights and political voice through the medium of journalism.