Dominant historiography in Singapore celebrates Sinnathamby Rajaratnam as one of the city-state’s founding national fathers, and the intellectual superintendent of state-sponsored multiculturalism in what has been characterized as an ‘illiberal democracy’. Little attention, however, has been paid to the extensive periods of Rajaratnam’s life in which he was not in governance with the People’s Action Party, and thus had considerable intellectual autonomy. This article examines the first of these periods—his sojourn in London from 1935 to 1947—marked by connections with overlapping communities of anti-colonial intellectuals drawn from Africa, the Caribbean, and East and South Asia. Close reading of Rajaratnam’s London lifeworld, his published fiction and journalism, and the many annotations he made in the books he read reveals a very different intellectual history than the one that we think we know, and allows us to better understand his lifelong uneasiness with capitalism and racial governmentality. Re-reading Rajaratnam as an autonomous intellectual disembeds his early intellectual life from the story of the developmental state, enabling a focus on the role of affect and form in his writing. The process also offers new insights into Singapore today, where the legacies of state-sponsored multiculturalism are increasingly challenged, and where citizens, residents, and migrants seek new forms of solidarity in and across difference.