Cassandra de Rolo

Cassandra de Rolo
Non-player character
Basic information
Biographical information
Full nameCassandra Johanna de Rolo[fn 1]
TitlesGuardian of Woven Stone[2]
Also known as
  • Cass (by Percy)
  • Kestrel (The Legend of Vox Machina)
LanguagesCommon, Elvish[3]
PlacesWhitestone, Tal'Dorei
FamilyDe Rolo family
ProfessionLeader of the Chamber of Whitestone
StatusAlive (resurrected)
Cause of deathKilled by Vex while dressed as a cultist ("The Final Ascent" (1x113))[4]
Mechanical information
Creature typeHumanoid
Level6 or higher[5]
51 or more[6]
First seen
Last seen
TelevisionThe Legend of Vox Machina (9 episodes)

Lady Cassandra Johanna de Rolo[7][fn 1] 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.[8]

Intro[edit | edit source]

"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."[9]

Description[edit | edit source]

Appearance[edit | edit source]

Cassandra, around 810 PD, 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.[10]

In 843 PD, "a good half or more of her hair has turned gray".[11]

Personality[edit | edit source]

In the aftermath of the murder of the de Rolo family Percy tried to get as far from Whitestone as possible, leaving Cassandra feeling abandoned by her brother and alone, dealing with the loss of their family.[12] Cassandra was captured by the Briarwoods and forced to follow their interest through manipulations and magic charm. Initially, she successfully resisted their attempts at breaking her will, but after her repeated attempts to escape and subsequent punishments. After suffering through a series of manipulation methods utilized by the Briarwoods, involving gas lighting and cycles of "giving then taking away; hurting then comforting", they managed convinced Cassandra that actually the world around her was torturous, the Briarwoods were the positive force in her life, and they are truly her family. Cassandra adapted to her condition, manifesting a Stockholm Syndrome, and became loyal to the family.[13][14]

This continued until Percy has returned to Whitestone and started to meet with Cassandra frequently, showing her a "glimmer of her past" before the Briarwoods and before the death of her family, which initiated the healing process.[13] She ultimately renounced the Briarwoods and fought for the liberation of her home.[15][16] Though skeptical and feeling unworthy, Cassandra took the leading position in the Chamber of Whitestone[17] and worked tirelessly to return the city to prosperity. In part, her efforts to overcome the trauma was to prove herself as a potential leader of Whitestone people and to prevail over the hardships by working together.[13] Even after the dangers had passed, Cassandra found herself in a dark place, feeling unworthy of anyone's trust.[18] Her brother has referred to her as "a bit of a brat". Their relationship is sometimes rocky,[19][20] though Percy has come around in recent years empathizing with her plight and giving her the support she needs.[21] Cassandra hopes to see the world outside of Whitestone, the city that has brought her so much pain through the years.[22]

In some ways, Cassandra emerged "a little" stronger and mentally healthier than her brother, acknowledging and accepting her trauma then taking steps to work past it.[23]

Biography[edit | edit source]

Before Campaign 1[edit | edit source]

Cassandra was the youngest child of the de Rolo family. As such, she was not expected to rule Whitestone, as her two eldest siblings were being groomed for leadership positions, and perhaps would have been married off as her family desired.[21] After the Briarwoods took over Whitestone, Cassandra freed her brother, Percy, and fled though the secret passage in the prison of the Castle Whitestone. While attempting to escape, Cassandra was hit by several arrows and left to bleed out, but was found in time, still alive by Father Reynal and a Whitestone hunting squad that recognized her, brought her back from the brink, and tended to her.[14]

In the time that she was recovering, the hunters and Reynal 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. Since 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.[14]

Campaign 1: Vox Machina[edit | edit source]

Arc 2: The Briarwoods[edit | edit source]

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.[24]

When Vox Machina investigated the Whitestone Castle, the party found Cassandra in the music room held hostage by Professor Anders who cast a Confusion and Minor Illusion on her, staging as if he slit Cassandra's throat and released her seemingly lifeless body from his grasp.[25][26] 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.

Cassandra told them a story after her recovery from the failed escape, contradicting the story the party heard from Archibald Desnay. As she recovered, Cassandra told the people of Whitestone about the unlawful nature of the Briarwoods rule, claiming that her family had fallen to a plague, and started to build a rebellion. At that time, the Briarwood rule was fresh and the denizens loyal to the de Rolo family felt ready to overturn it. After around two years of building the rebellion, just after dusk, Cassandra led a group of rebels through the secret passage into the castle. Preemptively informed of their plans by an informer within the rebel ranks, Lord Briarwood was waiting for them in the Parchwood Timberlands and slaughtered most of them, but Cassandra. The Briarwoods treated her well and tried to manipulate her with Sylas charm and wealth, but Cassandra said that it did not work on her, because of her enmity toward them. She claimed that her pastime was mostly about reading.[27]

While in the tunnels beneath Whitestone, Cassandra explained to Vox Machina that Sylas has abilities that influence minds and Delilah is a powerful necromancer.[28] The group eventually came across a chamber coated in bronze, where they noticed a smooth stone door that slides vertically[29] and eight opals embedded into walls, glowing while pressed.[30] When the party pressed on the seven of the opal stones and Cassandra pushes the eights stone near the stone door, walls of green glass came down from the ceiling, trapping Vox Machina on the inside and Cassandra on the outside of the cage.[31] Cassandra looked shocked this turn of events. When the Briarwoods entered the room through the shifted stone door[32] and the acid started to fill in the cage, 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.[12]

Feeling betrayed by Cassandra, Percy wanted revenge, and a new name appeared on on the barrel of his gun.[33]

During the fight in the ziggurat, Cassandra initially fought for the Briarwoods,[34] but as the it went on, she felt conflicted about her hostility toward Vox Machina and alignment with the Briarwoods, dropping her weapon.[15] 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.[35]

Once the party went back into the tunnels outside of the ziggurat, Cassandra was woken up and interrogated by Percy. Cassandra confessed that her job with the Briarwoods 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.[36] [15][16]

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,[16] and threw her body in an acid pit.[37] 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.[38]

After the successful revolt, Cassandra was hesitating to take up power over Whitestone because of her involvement with the Briarwoods and help to dissuade rebellions, which she has shared with her brother, Keeper Yennen, and Archibald. She feared they may reject her as a worthy leader as she did have a hand in their misfortune.[39] Later, while talking with Percy, Yennen, and Vox Machina, she proposed to use de Rolo treasury to compensate the people of Whitestone who were harmed during the Briarwoods rule and form Chamber of Whitestone to divide power between elective offices, with her taking a seat as an overseer of the chamber.[17]

Arc 3: The Chroma Conclave[edit | edit source]

After the Chroma Conclave'ss attack on Emon, Percy returned to Whitestone with refugees from the city, and told Cassandra about newly arose crisis. 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.[40]

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.[41]

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.[42]

During a meeting held in Whitestone discussing 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.[43] 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.[44]

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.[45] 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.[46]

Cassandra received Vox Machina when they returned from fighting Thordak, remarking they looked terrible.[47]

Arc 4: Taryon Darrington[edit | edit source]

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.[48] 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.[49]

Cassandra met and confusedly greeted the Trickfoot family while they were in Whitestone.[50]

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 using her sending stone to let her know about the development.[51]

Arc 5: Vecna[edit | edit source]

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.[52]

Cassandra was kidnapped by Vecna and disguised as a guard protecting the tower of Entropis, 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.[53] 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.[22]

Campaign 3: Bells Hells[edit | edit source]

In Brussendar 843 PD, Captain Kynan Leore reported to Keyleth that Lady Cassandra was occupied in Lyrengorn.[54]

During the apogee solstice in 843 PD, the next day after Bells Hells arrived in Whitestone, Cassandra returned from Westruun,[55] and was a part of a meeting in the Castle Whitestone's war room, where they outlined their plans regarding Bells Hells' infiltration of the Tishtan site.[11]

The Legend of Vox Machina[edit | edit source]

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.

Relationships[edit | edit source]

Percival de Rolo[edit | edit source]

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. Even though they didn't have deep emotional conversations about what they had been through with the Briarwoods, they grew more silly and playful with each other. They share the burden of the legacy of their family name.[21]

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[edit | edit source]

After her escape and subsequent capture by the Briarwoods, Cassandra was kept in the Castle Whitestone and treated like a part of the Briarwoods family. 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.

Character information[edit | edit source]

Official art of Cassandra, by Oliver Barrett from The World of Critical Role, page 275.[art 2]

Notable items[edit | edit source]

Abilities[edit | edit source]

Rogue abilities[edit | edit source]

Appearances and mentions[edit | edit source]

Behind the scenes[edit | edit source]

Cassandra is the name of a friend of Taliesin in real life, who knows about the show and thinks he's "such a weirdo".[60][61]

Quotations[edit | edit source]

  • Delilah: You could have been my daughter.
    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)[62]
  • 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)[63]

References[edit | edit source]


  1. 1.0 1.1 Tal'Dorei Campaign Setting (p. 33) gives her full name as "Cassandra Johanna von Musel Klossowski de Rolo".


  1. "The Legend of the Cast of The Legend of Vox Machina"
  2. 2.0 2.1 2.2 Tal'Dorei Campaign Setting, p. 33.
  3. "The Coming Storm" (1x73) at 54:08.
  4. Vex attacked the smaller figure on the left, which was later confirmed to be Cassandra. "The Final Ascent" (1x113) at 4:38:25.
  5. Cassandra has the 5th-level rogue feature Uncanny Dodge, and is multiclassed, making her minimum level 6.
  6. 6.0 6.1 Monster Analysis: Lord and Lady Briarwood, Round 2.
  7. Tal'Dorei Campaign Setting Reborn, Chapter 2: "Allegiances of Tal'Dorei", p. 51.
  8. See actor credit for Asset #10 on the Amazon Prime Video/Amazon Studios press page for the show.
  9. "Arrival at Kraghammer" (1x01) from 4:41 through 5:55. Excerpted from Percy's Intro.
  10. "Reunions" (1x33), part 1, at 1:16:05.
  11. 11.0 11.1 "The Promise and the Price" (3x77) at 3:14:35.
  12. 12.0 12.1 "Race to the Ziggurat" (1x34) at 1:26:38.
  13. 13.0 13.1 13.2 The Legend of Vox Machina Episodes 10-12 Q&A at 49:38.
  14. 14.0 14.1 14.2 "Talks Machina Special #5: Fireside Chat Q&A" (TMSx05) at 1:26:22.
  15. 15.0 15.1 15.2 "Race to the Ziggurat" (1x34) at 3:18:18.
  16. 16.0 16.1 16.2 "Denouement" (1x35), part 1, at 2:03:39.
  17. 17.0 17.1 "Winter's Crest in Whitestone" (1x36) at 2:17:31.
  18. "Winter's Crest in Whitestone" (1x36) at 2:24:28.
  19. "Talks Machina #21: Jugs and Rods" (TM1x94) at 37:41. "People think de Rolos are much warmer then they really are." Percy does not intervene in Cassandra's business and she does the same.
  20. "Talks Machina #29: Thar Amphala" (TM1x101) at 12:33. Taliesin likes to think of them as a "traditional Prussian family" where they don't communicate about anything that personal. The fact that they have any physical contact is notable. "They're warm for northern royalty, but they're cold people."
  21. 21.0 21.1 21.2 "Talks Machina #24: Taryon, My Wayward Son" (TM1x97) at 24:52.
  22. 22.0 22.1 "The Chapter Closes" (1x115) at 4:03:00.
  23. The Legend of Vox Machina Episodes 10-12 Q&A at 51:04.
  24. "Stoke the Flames" (1x30) at 2:36:25.
  25. "Reunions" (1x33), part 1, at 1:17:33.
  26. Matthew Mercer confirmed on Twitter that it was an illusion when Professor Anders cut Cassandra's throat.
  27. "Reunions" (1x33), part 2, at 39:32.
  28. "Race to the Ziggurat" (1x34) at 23:05.
  29. "Race to the Ziggurat" (1x34) at 1:08:33.
  30. "Race to the Ziggurat" (1x34) at 1:04:35.
  31. "Race to the Ziggurat" (1x34) at 1:13:32.
  32. "Race to the Ziggurat" (1x34) at 1:17:50.
  33. "Race to the Ziggurat" (1x34) at 2:07:18.
  34. "Race to the Ziggurat" (1x34) at 2:54:40.
  35. "Race to the Ziggurat" (1x34) at 3:48:17.
  36. "Denouement" (1x35), part 1, from 31:28 through 35:33.
  37. "Denouement" (1x35), part 2, at 0:01.
  38. "Denouement" (1x35), part 2, at 24:56.
  39. "Winter's Crest in Whitestone" (1x36) at 39:16.
  40. "Dangerous Dealings" (1x42).[citation needed]
  41. "A Cycle of Vengeance" (1x58).[citation needed]
  42. "Passed Through Fire" (1x69) at 1:38:28.
  43. "The Coming Storm" (1x73).[citation needed]
  44. "The Coming Storm" (1x73).[citation needed]
  45. "Clash at Daxio" (1x77) at 3:43:39.
  46. "The Siege of Emon" (1x78) at 57:08.
  47. "What Lies Beneath the Surface" (1x81) at 2:50:15.
  48. "Jugs and Rods" (1x94) at 2:15:20.
  49. "Jugs and Rods" (1x94) at 4:04:13.
  50. "One Year Later..." (1x95) at 3:26:53.
  51. 51.0 51.1 "Taryon, My Wayward Son" (1x97) at 1:20:04.
  52. "Thar Amphala" (1x101) at 55:36.
  53. "The Final Ascent" (1x113) at 4:44:51.
  54. "A Desperate Call" (3x36) at 30:06.
  55. "The Promise and the Price" (3x77) at 2:38:32.
  56. "Reunions" (1x33), part 1, at 34:14.
  57. "Reunions" (1x33), part 2, at 1:43:56.
  58. "Race to the Ziggurat" (1x34) at 2:57:13.
  59. "Trial by Firelight" (3x02) at 1:33:11. Not mentioned by name. "Found his sister."
  60. "Talks Machina #3: Cast Q&A, Prize Giveaway, and more!" (TMx03) at 47:00.
  61. "Talks Machina #5: The Siege of Emon" (TM1x78) at 1:06:35.
  62. "Denouement" (1x35), part 1, at 2:04:45.
  63. "A Cycle of Vengeance" (1x58) at 3:33:08.


  1. Screenshot of Cassandra de Rolo from "The Legend of the Cast of The Legend of Vox Machina". This file is a copyrighted work. Its use in this article is asserted to qualify as fair use of the material under United States copyright law.
  2. Official art of Cassandra, by Oliver Barrett from The World of Critical Role, page 275. This file is a copyrighted work. Its use in this article is asserted to qualify as fair use of the material under United States copyright law.