Organizational brokers, such as producers, diplomats, and middle managers, connect people within and across organizations. Trust in brokers promotes their effectiveness in connecting unfamiliar counterparts and transferring information between disconnected parties. Often, however, the very conditions that create the need for brokering, such as the existence of structural holes, undermine trust in brokers. We introduce an organizing framework to explain how fundamental features of brokering processes shape the perceived trustworthiness of brokers. Specifically, we describe how individuals make inferences about brokers’ ability, benevolence, and integrity based on the horizontal and vertical distances they bridge, the extent to which their brokering involves in-role versus extra-role behavior, and the extent to which they facilitate indirect versus direct exchanges between counterparts. Our model links situational features of brokering processes with established antecedents of interpersonal trust, thereby identifying challenges and opportunities for brokers and organizations.