How should a history of West Maui be approached? A typical large-scale narrative of West Maui moves from Native Hawaiians to missionaries to sugar to tourism. Whales and tourists come and go. But this type of history may be neither helpful nor insightful. Historical Investigations in West Maui seeks to extend known histories of West Maui in multiple directions. Messy, local histories help to open up the range of possibilities for action by giving us additional insight into the circumstances and conditions that previous generations faced. Historical knowledge helps to frame perceptions that organize space. Local histories therefore help to render visible aspects of historical space and time that have been obscured by overarching dominant narratives and timelines. Local history can disrupt social reproduction, leading to new ways of confronting the past and imagining people, the community, and the world. Making history complicated and messy is a way to question the existing structures of understanding and existence. Historical Investigations seeks to look at a wide range of topics: from Micronesian plantation labor in the nineteenth century to the history of Kaomi, Kauikeaouli’s co-ruler, to the South Asian Muslim awardee at the Māhele. It looks at historical processes, such as the evolution of the Kingdom educational system, the 1860s Lahaina famines, and the imposition of the Land Court system on land titles. By offering more local histories of West Maui, we are reminded that what exists is far from expressing all possibilities and that those neglected areas of political space can be reclaimed for different stories leading to alternative, preferred futures.