Cultural brokers create and capture value by introducing elements of one culture to markets in another. This study examines why audiences celebrate some brokers as appreciators who recognize an offering’s boundary-crossing appeal, while disparaging others as appropriators who exploit cultural divides for profit. Using a mixed-methods approach, I analyze 150 news articles on cultural appropriation and appreciation in markets to develop a theory on how audiences evaluate brokers based on their identities (i.e., “who” intermediates the exchange) and strategic choices (i.e., “how” brokers generate and distribute surplus). I then test this theory using pre-registered experiments with art producers. The findings reveal that evaluations are conditional on a broker’s identity, but brokers with disfavored identities can compensate for lower evaluations by capturing less value for themselves or redistributing it to the origin culture (i.e., forgoing some returns to brokerage). This study concludes with a discussion of implications for research on cultural brokerage, competitive strategy, and social stratification.