Prior to the United States' (U.S.) illegal occupation of the Hawaiian Kingdom government in 1893 and illegal annexation in 1898, literacy rates and educational attainment in the Hawaiian Kingdom were amongst the highest in the world. In contrast to the educational history of the 19th century, the usurpation of the Hawaiian educational system following the occupation of the U.S. gave way to a century of miseducation and marginalization. Today, more than 130 years after the illegal overthrow of the Hawaiian Kingdom government, the consequences of this event are omnipresent across all sectors of education, including higher education. The downward educational trend correlates with the evolution of the University of Hawai?i. This article examines the paradox and the dilemma of the University of Hawai?i to become a "Hawaiian Place of Learning" while also fortifying the U.S. occupation of the Hawaiian Islands. This article also highlights possibilities, programming, and philosophies from Native Hawaiian Student Services (NHSS), a co-curricular unit at the University of Hawai?i that both responds to the University's refusals and limitations by contextualizing Hawaiian student success in the 21st century and by looking back to the Hawaiian educational system of the 19th century as a blueprint for educational interventions today.