Between 1907 and 1914, Filipino lawyer, journalist, and nationalist Vicente Sotto found in Hong Kong a sanctuary from the clutches of the Americans. The city also provided him with a space in which to explore alternative ideas for both his own development and the future of the Philippine Islands beyond the confines of pan-Asianism and anti-imperialism. Using Sotto’s experience in Hong Kong as a point of access, this article demonstrates modern Asia’s anti-imperial era as a product of transimperial ‘connectivities’ and ‘ruptures’ wherein new political affinities were forged between like-minded Asians, while interstitial imperial spaces between colony and metropole carved space for radical, yet nuanced and inconsistent, visions of national independence to materialize—at the expense of abutting empires. It serves to decentralize the role of empire, conflating instead the activities of local, colonial, and imperial actors as a singular experience that shaped modern Asia’s revolutionary decades.