Small islands have often relied on the development of air transport to strengthen their economy, which often centers upon the tourism industry. However, such massive infrastructure projects become controversial, as the media has often framed infrastructure discourse into a conflict between environmental preservation and economic development. This paper explores the media portrayal of a proposal to develop an airport in the Ogasawara Islands, a remote Japanese region inscribed as a World Heritage Site in 2011. A thematic analysis was used to determine common themes found in 76 articles on the topic written between 2011 and 2019. These themes were then compared to an analysis of an island-wide census of residents, which collected opinions on the proposed airport and a follow-up interview conducted by the authors. The results reveal that the media had simplified and even misrepresented local opinion on the airport development as either pro-airport or pro-environment. Local islanders possessed complex opinions on the subject matter, and themes were identified beyond the typical economic development versus environment protection binary discourse associated with media coverage on infrastructure projects. Based on data collected from local interviews, this paper concludes with alternative scenarios to address local concerns.