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Much of the literature is concerned with big data detection techniques or operationalizing psychological drivers to explain individual decisions. This paper adds to the examination of classic fraud drivers in an understudied context. Utilizing a sample of 303 professional investing personnel, we face the possibility that each tripartite of the circumstances we study might combine to produce unusual outcomes. Using an experimental task that examines organizational culture, monetary rewards, and the threat of detection within a sympathetic context, professional investors are influenced by several combinatory conditions. Of note, intermediaries who enter into trades but who lack direct personal stakes in the outcome do not succumb to the same temptations. Additionally, we uncloak a “Robin Hood” effect where fraud decisions may be induced given a sympathetic client, regardless of organizational culture, (lack of) rewards, and a high chance of exposure.