This paper explores the topic of creative city planning in Singapore by comparing two educational cases for the Singapore Global Schoolhouse strategy: Yale-NUS College and NYU Tisch Asia. The partnership model, personified by the hyphens in the names of the liberal arts college Yale-NUS and medical school Duke-NUS, has demonstrated success in Singapore for its ability to merge the entre-preneurial enterprises and civic vision of a university. On the other hand, NYU Tisch Asia’s failure, while also stemming from other various factors, is primarily attributed to a one-sided, import-model without a clearly defined vision. Though there are other successful university cases that do not fall on a partnership model, such as business schools INSEAD and ESSEC, my choice to focus on Yale-NUS and Tisch stems primarily from their direct relationship to Singapore’s vision to be a creative city. Using both of these case studies, I argue that a schizophrenia between autonomy and re-striction has removed spontaneity from creativity in Singapore. Finally, I propose that a currency of trust is foundational to building not only a creative city but also a city that fosters creativity.