During the protracted Trojan War, the young prince Troilus seeks the affection of Cressida while the Greek and Trojan armies engage in a cycle of political maneuvering and military stalemate. The protagonist attempts to navigate the volatile intersection of romantic desire and the brutal realities of a war that renders individual loyalty fragile. Opposing him are the cynical observations of Thersites, the strategic machinations of Ulysses, and the shifting allegiances of the warring factions. The narrative framework utilizes a blend of high-flown rhetoric and biting satire to examine the breakdown of traditional heroic ideals within a claustrophobic, cynical environment.

Discussion often centers on the play's classification as a problem play due to its refusal to adhere to traditional generic boundaries. Readers frequently highlight the stark contrast between the romantic subplot and the bleak, disillusioned portrayal of the Trojan War. Critics often analyze the linguistic density of the speeches, noting how the characters use complex rhetoric to justify their shifting moral positions. The work is frequently cited for its modern-feeling cynicism, which challenges the heroic tropes established in earlier classical literature. Many readers find the play's lack of a clear resolution to be its most provocative feature, as it leaves the audience to grapple with the ambiguity of the characters' fates.