My thesis will reconsider the failed attempt by a number of Roman citizens to gain power in Rome in 63 B.C., commonly labeled “The Conspiracy of Catiline.” Two Roman authors, M. Tullius Cicero and C. Sallustius Crispus, were eyewitnesses to the events occurring that year and both wrote lengthy accounts about the discovery and suppression of the affair and its participants, who were planning to gain power in Rome through violent means. The participants planned murder and arson inside of Rome and threatened the city with an army in northern Etruria. Our sources tend to ascribe the leadership of these hostile activities to L. Sergius Catilina, presented as a debauched, and indebted, scion of a noble family. However, our sources discuss many other Roman citizens who participated with the affair. My thesis provides a comprehensive study of the terminology Cicero and Sallust used and the lexical choices they made to describe the affair and its participants. I examine the terminology that both these authors used to identify the affair’s context, primarily focusing on the terms coniuratio (“conspiracy”) and bellum (“war”), with the aim of showing how these terms and concepts become crystallized in this period. In addition, I examine the portrayal of the reported disturbances occurring inside and outside of Rome and the representation of the Roman citizens who were involved in them. By scrutinizing the terminology found in Cicero and Sallust’s accounts of the affair of 63, my thesis demonstrates that its common appellation as “The Conspiracy of Catiline” and all that it means – in terms of a single event with one leader – needs to be reconsidered due to the interpretations of its multifarious aspects.