Research on the economic context of Jesus’ teaching on wealth and exchange points to the need to take into account the nature and extent of market arrangements in first-century Roman Palestine. This context involves changing relations among reciprocity, redistribution, and market exchange. Studies of the relevant archeological evidence point to intra- and inter-regional trade, increasing specialization, and monetization. This article claims that in the Gospels we find Jesus recognizing a growing role for market exchange and a legitimate pursuit of economic gain through risk-taking alongside of the need for the practice of general reciprocity. Perceived hostility toward wealth and market exchange is explained in terms of the institutional features of the Palestinian agrarian economy, including extractive wealth transfer by the Roman state and religious authorities. The article concludes that Jesus’ teachings on wealth and market exchange have greater moral relevance to modern economic life than is commonly thought.