Like optics and medicine, the ancient art of divination overlapped with some forms of natural philosophy and demanded careful attention to the ordo creationis for clues about its divinely inspired operation. This chapter situates two of Shakespeare’s Roman plays, Julius Caesar and Antony and Cleopatra, in relation to historical and theoretical questions about divination in classical, medieval, and early modern texts, including his central source text Plutarch’s Lives. Shakespeare’s foregrounding of divination in these plays also registers the historical Caesar’s own role in historical accounts of divination both leading up to and following his assassination, especially since his death was understood as a disruption to the order of nature. Divination is a contested mode of knowledge in both plays that also identifies philosophical differences between characters and helps more broadly to recast Roman political history within the universalist theology of Christianity. Both Julius Caesar and Antony and Cleopatra foreground the figure of Octavius, who becomes the first Emperor of Rome and whose reign ushers in the “universal peace” in which Christ’s birth is possible. Divination also shapes an important racial dynamic in Antony and Cleopatra in ways that have not been recognized by critics.