This article examines the correlation between union activism, crime, and violence in the shipping industry in wartime China. Drawing on diplomatic and police records, shipping manifests, periodicals, and newspapers, the article deals with self-employed unskilled steamship attendants called “teaboys.” With insight into Chinese civilians’ underground struggle, the article contends that, steamship teaboys sustained their livelihoods during World War II by operating as everyday low-level spies for rival regimes. As workers, steamship teaboys pragmatically, without evidence of politico-ideological considerations, accommodated the needs of different belligerents in exchange for their own survival. Moreover, this article argues that the drastic socio-political upheaval in wartime China made these marginally employed shipboard attendants increasingly inclined towards a utilitarian patron-client relationship, originally forged in the mid-1920s when unionization began, and continued at the expense of their native-place ties and fictive family bonds. Impacted by the patron-client relationship in a climate where workers’ interests were protected by the armed forces of various regimes, the teaboys viewed unions as competitive sellers of muscle power in a market for crime and violence in industrial unrest.