This article captures the dynamics of a special case when it comes to media systems, namely the Åland Islands, or Åland, with 6,700 islands and 30,000 inhabitants. Åland is one of three self-governed areas in the Nordic region (the others being the Faroe Islands and Greenland) and is an officially monolingual Swedish-speaking part of Finland, where the majority speak Finnish. In this article, I describe how Åland, despite its small size, has a media system characterised by a diverse and complete offering of local media: two daily newspapers, its own public service and public service offerings from both mainland Finland and neighbouring Sweden, a commercial radio station, and several magazines. However, media diversity is limited by the fact that the same person – a local business tycoon, Anders Wiklöf – controls both newspapers. There is one main research question motivating this study: What are the specific features of the media system in Åland? To be able to answer that, I relied on the analysis of three sets of data: nine interviews, a two-part survey and the media policy adopted in 2018, and transcripts of the preceding political debate.