The Iliad in RWBY

To understand the references to The Iliad in RWBY, you must first understand the basic plot of The Iliad. King Agamemnon is leading the Greeks against the Trojans in the famous Trojan War. His best soldier is Achilles, while the Trojan’s best soldier is Hector. It should be said, that Achilles knows there is a prophecy that if he kills Hector he will be fated to die later. Patroclus is Achilles’ closest Comrade and is in a relationship with him, while Briseis is a Trojan that Achilles captures and also romances. Chryseis, daughter of the priest of Apollo, is captured in the same raid that takes Briseis, and Agamemnon takes Chryseis as his prize.

Chryseis's father tries to bargain for her life, but Agamemnon refuses, and her father prays to Apollo, who then curses the greeks with plague until Chryseis is returned. Achilles, determined to find the cause of the plague, swears to defend the Greek's best prophet if he will reveal why the gods are angry, as he is too terrified of Agamemnon to speak about it. Agamemnon agrees to give the girl up to stop the plague, but his seizure of Briseis immediately afterward is essentially in retaliation at Achilles for preventing Agamemnon from literally killing the messenger. (Agamemnon is an incredibly huge asshole.) This causes Achilles to stop fighting. Hector, the Trojan champion, similarly knows he is fated to die if he ever fights Achilles - and Achilles is all but untouchable anyway. So both Achilles and Hector have been avoiding fighting each other, drawing out the war.

Ozpin, who plays Agamemnon, loses his Maiden, Amber (Chryseis). He demands Pyrrha, who is Achilles, provide a replacement- except it's herself this time. So Pyrrha is both Achilles and Briseis here - she is the woman that Ozpin (as Agamemnon) demands be given to him. However, Pyrrha fears that this will separate her from who she loves: Jaune. In this way, Jaune plays both the roles of Patroclus and Briseis. He's both the Comrade Achilles is devoted to, and the romantic partner Achilles is upset about being separated from in order to appease Agamemnon. Achilles and Pyrrha both withdraw to brood about this.

The Iliad
Hector is a really interesting character - he's scholarly and kind and referred to by his peers as "a man of peace", yet he's the strongest Trojan warrior, and he's deeply devoted to his wife Andromache and their child. He can basically leave the city whenever he wants, but he stays and defends it for his father due to what I like to call a pathological sense of duty. Achilles on the other hand is kind of a bitter brooding rage monster because he's the greatest warrior ever but he's constantly insulted and used by Agamemnon and he knows he probably won't come home from the war alive because of fate.

Anyway, as the Greeks are losing ground to the Trojans, many Greeks, such as Odysseuss, come to try and convince him to rejoin the fighting. Patroclus in particular pleads with him to return to the fight.

Eventually the Trojans breach the palisade wall of the Greek camp and threaten their ships, and due to the desperation of the situation Patroclus takes Achilles armor and dresses up like him, and leads Achilles' men in a counter attack to drive the Trojans back. Unfortunately, Patroclus pursues them all the way back to the gates of Troy rather than being content with holding the fort, and this leaves him in a bad position. At the gates of Troy he faces Hector, and at this moment the god Apollo curses Patroclus with disorientation and confusion, leaving him unable to defend himself. As a result, Hector quickly kills Patroclus.

This is the central turning point in the plot of the Iliad.

Achilles is utterly devastated by the loss of Patroclus, blaming himself. In addition, his armor and weapons are lost when Patroclus falls while using them. Achilles goes into mourning. In order to lift Achilles' spirits and get him back into the fight, the gods make Achilles a new set of divine armor, including the legendary Shield of Achilles.

Achilles accepts these gifts, and equips them, declares that he is going to kill Hector even though he knows it will seal his fate. He then personally assaults the Trojan forces with such ferocity that the gods themselves have to step in to stop him from causing the city to fall before the appointed time. Hector, knowing he is doomed, bids a tearful farewell to Andromache at the gates of the city, and then rides out to face Achilles, where Achilles fairly decisively murders him to death.

How this works in RWBY
So, in RWBY, Pyrrha hesitates to take on the Maidenhood, agonizing over the decision. This is essentially "Achilles in his tent". Then, while she's hesitating, the enemy is busy winning, culminating in... the destruction of Penny Polendina. In RWBY, Penny dies Patroclus's death. Pyrrha, as Hector, is the one to destroy Penny, but once again an invisible actor confuses and disorients one of the fighters, leading to one of them being swiftly struck down.

And then Pyrrha, as Achilles, is devastated by Penny's death and feels personally responsible. And once again, Achilles is deprived of his equipment, and it's not until someone brings Pyrrha her weapons that she's able to restore some modicum of functionality.

At which point she commits to doing as Agamemnon wishes, even though she knows it will probably result in the loss of everything she holds dear.

Cinder as Achilles begins her relentless, unstoppable assault at this time, and Pyrrha (as Hector) says goodbye to Jaune (as Andromache) and goes off the fight Cinder, knowing she'll almost certainly die, but believing it's her duty to die in this fashion.

Once again Pyrrha puts up a remarkably good fight, and at times it seems like she might have a chance of winning - until Cinder does things which feel like outright cheating. I feel that this is meant to thematically echo how unfair all of the fights in The Iliad are, and how blatantly the gods constantly intervene to tip the scales in the direction they want them to. Especially the shot of the disintegrating arrow that reforms on the other side of her shield, to me, hammers home the idea that this is not a fair fight.

At the end, Pyrrha dies - and this time she dies not just Hector's death but also Patroclus's, because Pyrrha dies the death that separates Achilles from his beloved.

And once again, Achilles' armor and equipment are lost.

And this time, the legendary Shield of Achilles is forged to replace Pyrrha's lost equipment.

Hasn't Happened Yet
After killing Hector, Achilles desecrates the body and refuses King Priam (Hector’s father) the opportunity of a proper burial. The Iliad makes a big deal out of this. King Priam goes unarmed in disguise to Achilles' camp, which is basically suicide, sneaks in to Achilles tent, gets on his knees, and begs Achilles for Hector's body back.

Achilles is deeply moved by this act and they have a long conversation and Achilles and Priam come to understand one another, and for once Achilles calms down and doesn't do the most spiteful thing he can think of, and he not only gives Priam Hector's body back but effectively forces a truce by refusing to fight for two weeks so that Priam has time to perform the full funeral rites for Hector and mourn him. It's the emotional climax of the Iliad, which is when Achilles finally regrets everything and comes to mourn his own nemesis.