Cassandra de Rolo

Lady Cassandra Johanna von Musel Klossowski de Rolo is the head of the Chamber of Whitestone and is the youngest sister of Percy's six siblings. As an NPC, she is played by Matthew Mercer.

Excerpt from Percy's 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 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. She awoke back in Whitestone as a hostage of the Briarwoods. Over the next several years Cassandra would originally attempt to aid the rebellion, but it is later revealed that, due to them mentally and/or emotionally manipulating her, she was feeding the Briarwoods information so that the rebellion would fail.

Archibald Desnay claimed that Cassandra was helping the rebellion.

Cassandra was reunited with Percy and met the rest of Vox Machina when she was found by Vax. She seemingly had her throat cut by Professor Anders, but this was later revealed to be an illusion. She joined the party to fight the Briarwoods.

After walking them through the cavern down to the ziggurat, Vox Machina came upon a room covered in bronze. By pressing on opal stones on the walls, mysterious green glass residuum trapped them in (sans Cassandra). As Lord and Lady Briarwood stepped into the room, she revealed her alliance to the couple and denounced her relation to her brother, but not without looking conflicted.

At the ziggurat, Cassandra initially fought with the Briarwoods against Vox Machina; but as the battle progressed, the mental strain on her mind from her competing conscious overwhelmed her and she dropped her weapons, stunned. Grog grabbed Cassandra by the neck and dangled her off the edge of the ziggurat. Percy pleaded with him not to. Vax questioned why Grog shouldn't just drop her. Percy insists that the amount of time Cassandra has spent with Briarwoods should be taken into account when considering her betrayal. Vax punched her across the jaw, knocking her unconscious and the party tied her up.

Along with Lady Briarwood, she was taken to the tunnels as the party fled away from the pyramid until they stopped to heal. This is when Percy woke and interrogated her. Cassandra admitted to collaborating with the Briarwoods so that rebellion would fail. This 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.

After fighting Orthax, Percy acqusitioned his sister to kill Lady Briarwood, so Cassandra proceeded to lay the finishing blow but not with Lady Briarwood saying "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," stabbing her, finally freeing herself and Whitestone from the tyrannical rule. In some sort of vengeance, Cassandra dragged the body to the acid factory underground and threw the remains of Lady Briarwood in a vat.

In the beginning days after the successful revolt, Cassandra revealed her hesitation to her brother, Brother 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.

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 and 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.

Trivia

 * When Professor Anders cut Cassandra's throat in front of Vax'ildan, it was an illusion.
 * Cassandra is the name of a friend of Taliesin in real life, who knows about the show and thinks he's "such a weirdo".
 * Many Critters have speculated that while Kynan served as Cassandra's bodyguard, they began a romantic relationship. While Matthew Mercer hasn't confirmed it yet, he has stated that their shared history with Ripley and their equally stressful positions of power "certainly sounds like a set up for a meaningful romance".