This chapter focuses on brokers and brokerage in the context of cross border smuggling or illicit trade. Drawing on illustrative case study material from the borderscapes of eastern and western Afghanistan, we shine a light 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. By focusing on their lives we aim to achieve two things: firstly, to present new empirical evidence on brokers, so as to better understand their lives, motivations, roles and effects – and in particular, how they adapted to border hardening and closures. Specifically, we explore the positionality of brokers in terms of their personal backgrounds, their ability to straddle lifeworlds, the ‘deal spaces’ they occupy, the resources and commodities they move, and the key pathways, corridors and choke points that channel and direct trade flows. We also examine the dynamics of brokerage, including the ways that brokers find solutions or ‘fixes’ to problems but rarely resolve them, and how brokers adapt to (or fail to adapt to) moments of rupture in fluid trading environments. Finally, we reveal the effects of brokerage in terms of how brokers cumulatively shape the ways in which states and markets function in marginal frontier and borderland environments. Though their agency is circumscribed, brokers are not merely mediators; they play a role in transforming and reconfiguring connections and relationships within political and market systems.