In Roman society, freed slaves were elevated to a citizen-like status, yet they never had the full rights of their free-born counterparts. Despite the inequality of the system, many freedmen appear to have found great success in the realm of business. This report endeavors to reveal why it was that this group prospered within the Roman economy using a pseudo-Darwinian perspective. Scholarship has, for the most part, tended to avoid Darwinian lines of thought in sociological studies but this report shows the power of this type of thinking. The first chapter clarifies the nature of slavery in the Roman world and the wide variety of experiences that slaves could have. Chapter two considers the different ways that slaves could be manumitted and how a freedman’s status could differ depending on the formality of his release from servitude. The third chapter examines the literary representations of freedmen in the genre of comedy and Petronius’ Satyricon. Chapter four turns to the archaeological evidence and provides a sense of how freedmen represented themselves to the wider community. Lastly, the fifth chapter, using a pseudo-Darwinian model, will show that the image of the successful freedman is not an anomaly of the archaeological record or a trope of Latin literature but an inevitable outcome of the intense selection that slaves underwent. / text