This chapter focuses on a particular kind of trading space: borderlands and frontier regions that straddle the margins of one or more states. It also focuses on brokers and brokerage in the context of cross border smuggling or illicit trade. The chapter provides a tentative comparison of borderland brokers within different borderland spaces. Borderland trade brokers mediate, filter and channel flows of commodities and resources across borders. Drawing on illustrative case study material from the borderscapes of eastern and western Afghanistan, the chapter focuses on the lives of two brokers who act as go-betweens and gatekeepers in these complex and often conflictual transnational trading networks. One is a tribal broker in Nangarhar province on the Pakistan border, and another is an illicit trader in Nimroz province on the Iranian border. Apex brokers occupy key synapses that shape the overall balance of power or distribution of resources within political settlements.