Religious leaders throughout the Greco-Roman world warned against the improper use of speech.  Yet, one biblical verse shatters this taboo by mandating confrontational speech with the power to hurt and shame: Leviticus 19:17 commands that one actively rebuke his or her fellow.  For some, such as the Qumran community, the mandate of rebuke functioned as a means of ensuring social control through official regimented reproof.  For others, such as the earliest generations of rabbis, the potential eruptive force of rebuke was far too great prompting them to curtail the application of the verse entirely.  Between these two poles of embrace and rejection some early Christian texts encouraged rebuke as a means to securing communal boundaries, while other passages opted for a non-retaliatory response that forbade any harsh language.  In this paper I describe the diverse spectrum of responses to this biblical injunction and argue that the degree to which each community accepted the scriptural directive correlates with their respective political aspirations.  The semi-isolated members of the Qumran center strove to forge a system of complete control over daily life while the culturally insecure position of the early rabbis motivated them to formally recognize the danger of verbal offense.  The mixed message that we find in the gospels reflects the tension between the ideal of love and humility and the practical demands of communal stability.  The juxtaposition of these traditions reveals the divergent ways religious leaders of antiquity wielded this biblical passage as a means to ensuring their formative goals.