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My paper analyzes the autonomous social networks constructed by free and enslaved black coachmen (negros caleseros) in nineteenth-century Havana. As a vital colonial hub, the city’s economic and social circuits heavily depended on their labor. A bustling metropolis, where personal transportation played a vital role, black coachmen facilitated the daily transactions of the well to do. As the chauffeurs for middling and upper members of Spanish Cuban society, black coachmen possessed a relatively high degree of autonomy when compared to most peoples of African descent; they traversed the entire city, entering and reentering economically and racially segregated neighborhoods, often unimpeded and many times unaccompanied by Spaniards. Thus coachmen served a dual purpose in Cuban society; they provided Spaniards with vital transportation services, and they functioned as messengers and conveyors of news and information for the enslaved and free population of color. These autonomous African networks improved the overall economic efficiency of the island, but they also possessed the potential to destabilize society. It was no coincidence that masters often identified coachmen as habitual runaways and that authorities accused them of actively participating in slave rebellions and conspiracies. This paper addresses the following quandary confronting nineteenth-century Cuban society: however ominous the implications of African mobility to social order, the efficiency of the entire economy depended on the ready availability of inexpensive African labor. For dominant groups the most challenging aspect of this social and economic relationship was how to maintain the current racial hierarchy without circumscribing the autonomy of African labor.