A connection management system comprises a wireless speaker including first and second connectors for communicating with two selected audio content source devices, respectively, of at least three audio content source devices; a rules engine that establishes a set of conditions under which the at least three audio content source devices share the first and second connectors of the wireless speaker; and a device allocation system that forms a first communication path between one of the two selected audio content source devices and the first connector of the wireless speaker and forms a second communication path between another of the two selected audio content source devices and the second connector of the wireless speaker at a time in accordance with the set of conditions established by the rules engine.