Virgil intends Aeneas to become the “Roman Hercules,” for he depicts a hero hounded by Juno’s wrath and repeatedly uses the word labor for each fresh trial the demi-god faces, the first instance being in line 10 (Galinsky 1972, p. 132). Galinsky argues that because Aeneas was the peculiar property of noble Roman families like the Julians, Augustus became a new Hercules by association, a clear nod by Virgil toward Augustus’ eventual deification (p. 138). The parallel drawn among Aeneas, Hercules, and Augustus is not, however, straightforward praise for Augustus. As several scholars point out, the story of Cacus’ defeat, narrated by King Evander in book eight, raises questions about Virgil’s intent in associating the three men. For example, Ferenczi (1999) argues that Hercules is so enraged against Cacus that he has no claim to moral superiority over the monster, which makes him less a model of virtus than either Aeneas or Augustus in Virgil’s eyes. The premise is sound, but whereas Ferenczi claims that the characterization of Hercules undermines the parallel between him and Aeneas (p. 334), I will argue that Virgil deliberately chose an ambiguous hero to juxtapose with Aeneas, so that Aeneas’ wrathful defeat of Turnus would call into question his moral superiority over his enemy, just as Hercules’ conquest of Cacus does. In fact, Virgil characterizes not only Cacus and Turnus as bestial (see Galinsky, p. 144) but also Hercules and Aeneas. Underscoring the ambiguity of the Cacus episode, Secci (2013) claims that Virgil acknowledges the difficulty of creating Rome’s foundation story from the traditional myth of Aeneas when he depicts Evander as a myth-maker who deliberately ignores the crux of the traditional labor, taking Geryon’s cattle, and instead embellishes a secondary story, the defeat of Cacus (Secci, p. 196). By making a lesser-known myth the central aetiological myth, Evander and Virgil subtly undermine the heroism not only of Hercules but of the new Hercules, which in turn raises questions about Augustus’ greatness. Virgil again emphasizes a secondary aspect of a Herculean labor when he characterizes Aeneas’ ascent from the underworld as the true Herculean task (hic labor est, 6.129); the traditional labor was to descend and retrieve Cerberus. Aeneas’ impressive triumph over death foreshadows that of Augustus, but what sort of triumph is it that returns through the gate of false dreams (Aen. 6.896-98)? A few other instances of the word labor in the Aeneid raise similar questions. Hence, by associating Aeneas with Hercules, both in the Cacus episode and in his repeated usage of labor, Virgil deliberately underscores the ambiguity of Aeneas’ character: he is both the godlike, dutiful founder of Rome and an emotional man alternately swayed by love, regret, and wrath. Virgil draws a parallel between Aeneas and Hercules not only as praise for Augustus, the self-proclaimed new founder of Rome (Suetonius, Vita Augusti 7), but also as a subtle warning to his readers that a demi-god like Aeneas or Hercules can bring indiscriminate destruction to friend and foe.