It has generally been thought that Hannibal was a hostile individual and despised in Roman society because of his non-Roman status and his apparent tendency to be deceptive, cruel and savage. Yet, our understanding of Hannibal as a character is limited. This thesis attempts to address his characterisation through an examination of his night-time military exploits, and argue that our knowledge of Hannibal can be expanded upon by examining how Livy characterised Hannibal in his account of the Second Punic War. Furthermore, this thesis takes a fresh approach to Hannibal’s characterisation, considering Livy’s use of ‘the night’ in association with military activity, and revealing that Hannibal displayed traits that the Romans themselves valued. Thus, Hannibal’s character is developed through a nocturnal military setting, and he becomes comparable to Rome’s finest generals, including Fabius Maximus, Marcellus and Scipio Africanus. Similarly, it is also shown that he exhibited Roman military virtus in place of the traits traditionally thought to be synonymous with the non-Roman. By analysing the character of Hannibal in this manner, we reveal that in Roman thought he was an ambiguous character, whilst simultaneously highlighting how the Romans both perceived and used the night within the context of the army.