For canonical Philippine writer Nick Joaquin, the American occupation has rendered insurrectionary action unfeasible. Thus, Joaquin is often read as lionizing the Spanish period in comparison. However, I challenge such readings to argue that Joaquin’s engagement with the Spanish past reflects a search for the conditions of possibility for revolution. This search, however, remains a fraught enterprise. Though Joaquin is lauded for depicting nonnormative, counter-hegemonic ideas of who qualifies to be a Philippine historical and revolutionary subject, I argue—by examining three of Joaquin’s works—that the tenability of his representations remains delimited by his positionality as a cosmopolitan mestizo.