Troilus and Cressida is from what my friend David refers to as “Shakespeare’s bad-mood period.” There is moral dubiousness. There is (I’ll call it) character lurch, where a main character becomes a completely different person for reasons that are not clear. There is interminable holding-forth by important leaders, which you can get for free at a staff meeting. But! The play is based on the real Trojan War as recounted in The Iliad and I love anything about the ancient Greeks. In some ways Troilus is a stand-in for more familiar heroes (Ulysses, Achilles, Hector). Cressida is written to be like Helen, launcher of a thousand ships. Each of those famous names is also a character in the play, although Helen never appears onstage.
The Reduced Shakespeare Company tweeted: “Trojan wars are complicated, and Trojans sometimes break.”
What happens in Troilus and Cressida
Troilus is a Trojan prince and warrior. Cressida is the daughter of a Trojan priest who defected to the Greek side.
Troilus is in Shakespearean-love-at-first-sight with Cressida. Pandarus, Cressida’s uncle, unapologetically acts like a pimp and connives to bring them together.
In the Greek camp, Ulysses (a general) blames his army’s morale problem on Achilles, who is their greatest warrior but who refuses to fight and instead keeps malingering in his tent with his lover Patroclus.
Hector is the greatest Trojan warrior (so, Achilles’ counterpart). He challenges the Greeks to single combat. Ulysses sends his second-best fighter, Ajax, instead of Achilles, on the logic that being snubbed will wound Achilles’s pride and get his head back in the game. Also it would be bad for morale if Achilles died, and morale in the Greek army is already bad.
Pandarus succeeds in bringing Troilus and Cressida together. They make some nice promises, don’t actually get married, but do go off to spend the night together. Which is not even when things get morally dubious.
Cressida’s father (remember, he is Trojan but defected to the Greeks) asks the Greek commanders to exchange a Trojan prisoner for his daughter so he can be reunited with her. The trade is made, to Troilus and Cressida’s total shock.
Ajax and Hector fight but neither one can get the upper hand.
There is a bit of silly politicking.
Ulysses pimps out Cressida to the entire Greek camp and then hands her over to Diomedes, a prominent Greek. Cressida, making the abrupt transition from driven snow to bawdy bawd, cheerfully goes along with all this and agrees to be Diomedes’ lover. Troilus watches. I’m not blaming a girl for doing what she has to do, but by Shakespeare’s standards the moral low ground is now below sea level.
Hector goes into battle. The more-miserable-than-ever Troilus goes with him.
The Trojans drive the Greeks back, but Patroclus is killed. That finally brings a furious Achilles back into the war.
Achilles and Hector fight mano-a-mano. Achilles can’t win in a fair fight, but later he sneaks up on Hector unarmed and kills him. This is not how it went in The Iliad and it makes Achilles look like a right coward, but that action definitely fits the “Achilles” that Shakespeare created.
The play ends with the Trojan army retreating to mourn Hector. Troilus remains miserable and heaps abuse on Pandarus, who deserves it.
For actual scholarship, try out the SparkNotes page. Troilus and Cressida is a confusing and sometimes unsatisfying play, and I found the scene-by-scene analysis and commentary helpful.