Cassandra de Rolo

Lady Cassandra Johanna de Rolo is the head of the Chamber of Whitestone, the youngest sister of Percival de Rolo's six siblings, and only other surviving member of the De Rolo family.

As an NPC in Critical Role, Cassandra is played by Matthew Mercer. In The Legend of Vox Machina, she is voiced by Esmé Creed-Miles.

Intro
"One day, a mysterious couple, named Lord and Lady Briarwood, came to the court. During a feast held in their honor, the Briarwoods violently took control of the castle, killing or imprisoning everyone who would stand in their way. Percy awoke chained in the dungeon, only to be freed by his younger sister. Together they fled, chased by the Briarwoods' men. As they ran, Percy's sister took several arrows to the chest and fell."

Appearance
Cassandra is a young human woman in her late teens/early twenties. She has dark brown hair with a few streaks of white at her temples, most likely due to her mental and psychological hardship.

Personality
Cassandra is an extremely conflicted character. While Percy tried to get as far from Whitestone as possible, Cassandra was left to deal with the loss of her entire family as well as being abandoned by her brother. Cassandra suffered from severe psychological trauma which led to a feeling of conflicting loyalties during the rebellion in Whitestone. However, she ultimately renounced the Briarwoods and fought for the liberation of her home. Though skeptical and feeling unworthy, Cassandra took the leading position in the Chamber of Whitestone and worked tirelessly to return the city to prosperity. Even after the dangers had passed Cassandra found herself in a dark place, feeling unworthy of anyone's trust. Her brother has referred to her as, "a bit of a brat" and their relationship is a bit rocky, though Percy has come around in recent years coming to understand her plight and giving her the support she needs. Cassandra hopes to see the world and travel far from the city that has brought her so much pain through the years.

Background
Cassandra was the youngest child of the de Rolo family. After the Briarwoods took over Whitestone, Cassandra freed her brother, Percy, and fled. While attempting to escape, Cassandra was hit by several arrows and fell in the snow, bleeding out. She was found still alive by a Whitestone hunting squad that recognized her, brought her back, and tended to her.

In the time that she was recovering, they were discovered by the Briarwoods' lackeys and slaughtered, and the Briarwoods completed nursing Cassandra back to health. She had to witness the corpses of her whole family hung on the Sun Tree. She was subjected to brainwashing and was forced to become a member of the Briarwoods family, eating breakfast and dinner with them every day. As she was a connection to the old regime, they saw Cassandra as an asset to keep the people of Whitestone under control. She became their plaything and a quasi-adopted child. For years, she repeatedly attempted to escape and they would punish her for it. They eventually secured her loyalty through a Stockholm Syndrome-esque process. The Briarwoods began to use her as an infiltration agent to quash potential rebellions in Whitestone. She'd ask around about starting a rebellion, find out where the rebellion was building, and report back, and the rebellion leaders would be wiped out.

Archibald Desnay revealed to Percy that Cassandra had survived the Briarwoods' attack on Whitestone, and was now a personal assistant and slave to the Briarwoods. While used as a symbol of the Briarwoods' dominance, she had been feeding information to the rebellion for years.

When entered the Whitestone Castle, Vox Machina found Cassandra held hostage by Professor Anders who cast a Minor Illusion and Confusion, staging this as if he slit her throat and released her limp, seemingly lifeless body. After the party dealt with Professor Anders and his helmed horrors and they figured out the nature of the illusion, Cassandra reunited with Percy, and offered to lead Vox Machina underground to the ziggurat and join the fight against the Briarwoods. She explained that after recovering from the attack, she was helping a group escape from the castle when Sylas Briarwood found and slaughtered them, sparing Cassandra. She was offered power and wealth by the Briarwoods, and spent her time planning the rebellion.

While in the tunnels beneath Whitestone, Cassandra explained to Vox Machina the dangers of the Briarwoods: Sylas and his ability to influence minds, and Delilah and her powerful necromantic magic.

The group came across an entirely bronze room, and when they pressed down opal stones in the room walls of green glass came down from the ceiling, which trapped Vox Machina inside the room and Cassandra on the outside. The Briarwoods appeared next to Cassandra, and acid started to pour into the room. Cassandra told Percy that she had a new family with the Briarwoods after he left her to die, but even as she seemed to speak with conviction, she was clearly conflicted while betraying her brother.

At the fight in the ziggurat, Cassandra initially fought for the Briarwoods, but as the fight went on the conflict in her mind caused her to drop her weapons against Vox Machina. Grog dangled Cassandra over the edge of the Ziggurat, but Percy convinced him that the amount of time Cassandra spent under control of the Briarwoods should be taken into account when considering her betrayal. Vax knocked her unconscious and she was tied up and carried out of the Ziggurat by Grog.

Once in the tunnels outside of the Ziggurat, Cassandra is woken and interrogated by Percy. Cassandra confessed that her job was to communicate with those organising the rebellion and inform the Briarwoods about who planned to rise against them. She explained she didn't know why she helped the Briarwoods, which is most likely due to a sort of Stockholm Syndrome, as she depended on the Briarwoods to survive for years and having lost her family was treated as a daughter of sorts by them. She informed Vox Machina that while she didn't know the details of the purpose of the Ziggurat, she knew there was a blood ritual that she was going to be involved with.

After fighting Orthax, Percy invited Cassandra to land the killing blow on Delilah Briarwood. Lady Briarwood told her "You could have been my daughter" to which Cassandra replied: "No. Cassandra is a De Rolo, and you took them away from me. And now we're taking everything from you." Cassandra then stabbed and killed Delilah, and threw her body in an acid pit. She left the castle with her brother to tell the people in Whitestone that they were free from the Briarwoods for the first time in five years.

In the beginning days after the successful revolt, Cassandra revealed her hesitation to her brother, Keeper Yennen, and Archibald about taking up power at Whitestone because of her involvement with the Briarwoods and helping them dissuade any previous rebellions. She feared they may reject her as a worthy leader as she did have a hand in their misfortune.

Later, while talking with Brother Yennen and Vox Machina, she agreed to take up a seat at the newly formed Council of Whitestone to divide power.

Percy returned to Whitestone with refugees from Emon, and told Cassandra about the Chroma Conclave, and its attack on Emon. When Percy asked about starting research for defeating the dragons, Cassandra informed him that Eskil Ryndarien was still in the city researching the ziggurat.

Later, Cassandra supplied some gold and Residuum pieces to Vox Machina to aid their fight against the dragons.

In the wake of Hotis's attack, Cassandra commanded the guards of Whitestone to search the city for assassins. The next day, Cassandra was a part of the group seeing Vox Machina off before they went to the Feywild. Cassandra asked Percy to try to stay alive. She told Vox Machina that their influence on the city had saved it many times, and that it was important for them all to come back alive.

After Percy died during the fight with Anna Ripley, he was brought back to Whitestone for a resurrection ritual. Cassandra walked in after the successful ritual, and was very relieved that Percy was alive once again.

During a meeting held in Whitestone to discuss the next stages of the fight against the Chroma Conclave, Cassandra expressed her concerns that a retaliation from Thordak was imminent. She agreed with Allura Vysoren and Shaun Gilmore that consolidating the allies that Vox Machina had gathered to strike against Thordak first was the best course of action.

Cassandra was horrified when Raishan revealed herself, after being disguised as Seeker Assum. She expressed her fears to Percy, telling him that she couldn't continue to protect Whitestone if Raishan turned on them.

Cassandra greeted Vox Machina after they returned from Fort Daxio, and led them to the ziggurat where Raishan had returned with the real Seeker Assum. During the meeting they discussed the attack at Daxio, and the plan of attack for Emon.

Before Vox Machina left for Emon to fight Thordak, Percy warned Cassandra that if they failed to defeat Thordak, Whitestone would be at risk. Cassandra reassured Percy that Allura could protect Whitestone by maintaining the barrier. Cassandra then expressed that she had faith that Vox Machina would defeat Thordak.

Cassandra greeted Vox Machina as they returned from fighting Thordak, remarking they looked terrible.

After Percy had returned to Whitestone, Cassandra was relieved to learn that he planned to stay to help run Whitestone, as she was exhausted and couldn't do it by herself.

The next morning, she discussed the responsibilities of being the Grand Mistress of the Grey Hunt with Vex, and told her what little information she could about the ritual Vex would need to complete to receive the title. After Vex successfully completed her first hunt, Cassandra congratulated her and welcomed her to the Chamber of Whitestone.

Cassandra confusedly greeted the Trickfoot family while they were in Whitestone.

Cassandra was woken by Percy after Vex shot an Oracle arrow through the siphon under Whitestone, and had a vision of the Shadowfell. Cassandra contacted Allura with a Sending Stone to let her know about the development.

After Vox Machina returned from Ank'Harel after fighting the Remnants, Percy revealed to Cassandra that Delilah Briarwood was alive once again. Cassandra is horrified by the news, and is determined that Delilah has to die again.

Cassandra was kidnapped by Vecna and disguised as a guard, along with Gilmore and Kaylie. She was accidentally killed by Vex'ahlia but was resurrected by Pike. Both she and Kaylie were taken safely back to Whitestone by Gilmore.

Cassandra was tended to in Whitestone and recovered from her injuries. Within a year, her experience with death combined with the past trauma she suffered under the Briarwoods led her to a dark place, much like what Percy went through. Percy is there for her and helps her work through it, giving her the support she needs to make it through and eventually heal. Vex'ahlia also helps train in her ways to protect herself so that Cassandra will never feel like a pawn. Cassandra continues to reside in Whitestone, though Percy and Vex ensure that she has plenty of opportunities to travel and see the world.

Post-Campaign
In Brussendar 843 PD, Captain Kynan Leore reported to Keyleth that Lady Cassandra was occupied in Lyrengorn.

The Legend of Vox Machina
In the animated adaptation, Cassandra was tutored as a child by Professor Anders alongside her brother, Percy. She didn't pay attention in class, preferring to annoy her brother while Anders looked away. After the Briarwoods took over Whitestone, she attempted to flee with Percy, but was hit with several arrows and captured. For many years, she stayed with the Briarwoods, who paraded her in the streets. However, she was secretly feeding information to the Whitestone resistance under the codename Kestrel.

Vox Machina attempted to rescue Cassandra from Professor Anders' estate, but Anders held her at knifepoint before slitting her throat in front of Percy. Keyleth managed to heal her with help from Vax. After Anders was killed, Cassandra reunited with her brother. She expressed disappointment at being left behind, but accepted his apology. She joined Vox Machina as they fought against the army of undead raised by Delilah and urged Percy to speak to the citizens of Whitestone, insisting that he had to be the one to do it since none of them trusted her anymore.

Percival de Rolo
Percy is one of Cassandra's older brothers. During the Briarwoods' attack on Whitestone, Cassandra freed Percy from captivity, but was shot with several arrows as a result, and Percy left her behind after assuming she was dead. The siblings were happily reunited, but due to a Stockholm Syndrome-like loyalty to the Briarwoods due to depending on them for years, Cassandra turned on her brother, and said she stopped being a de Rolo when Percy left her for dead. Cassandra appeared conflicted about what side she was one, and when the Briarwoods were defeated, she confessed her role in sabotaging the previous rebellions. Percy forgave her, and despite her hesitance, agreed to form a new Chamber of Whitestone, which she would lead.

Once Percy was resurrected after the fight with Anna Ripley, Cassandra was very relieved to see that Percy was alive again.

After the Chroma Conclave was defeated, Cassandra was relieved when Percy said he was going to stay in Whitestone to help her run things, as she was exhausted from doing it herself.

In the aftermath of being kidnapped by Vecna, her brush with death and past trauma from the Briarwoods led Cassandra to a dark place. Percy gave her the support she needed to work through it and eventually heal.

Briarwoods
During the rebellion, Cassandra was leading a group out of Whitestone Castle when they were found by Sylas Briarwood. Sylas slaughtered the group but kept Cassandra alive, keeping her in the castle and treating her like a daughter. This led to Cassandra forming a Stockholm Syndrome type bond to her captors, and caused her to turn against Percy. However, after the Briarwoods were defeated, Cassandra realised where her true loyalties were, and killed Delilah in revenge.

Notable items

 * Her mother's ornamental armor.

Rogue abilities

 * Sneak Attack
 * Uncanny Dodge

Appearances and mentions

 * Campaign 1
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * Campaign 3
 * One-shots
 * The Legend of Vox Machina
 * One-shots
 * The Legend of Vox Machina
 * One-shots
 * The Legend of Vox Machina
 * The Legend of Vox Machina

Behind the scenes
Cassandra is the name of a friend of Taliesin in real life, who knows about the show and thinks he's "such a weirdo".

Quotations
Cassandra: No. Cassandra is a de Rolo, and you took them away from me. And now we're taking everything from you. (as she stabs Delilah)
 * Delilah: You could have been my daughter.
 * Cassandra: I cannot express, truly, how important your influence has been in this city, and I don't think you realize just how many lives here are for the better since you've walked into our humble home. And it is for that reason that I request, on behalf of all of us here in Whitestone, that you come back safe. That is all. Good luck. (before Vox Machina leave for the Feywild)