Briarwoods

The Briarwoods are Sylas Briarwood and Delilah Briarwood, a married couple originally hailing from the continent of Wildemount, specifically the region of Wynandir. They arrived as guests at Whitestone Castle several years before the events of Critical Role. They were responsible for the deaths of Whitestone's rulers, Frederick de Rolo and Johanna de Rolo, as well as all of the de Rolo children, save Percival and Cassandra.

Background
Very few things were generally known about the Briarwoods prior to their arrival in Whitestone. They claimed to be nobility from Wildemount and presented themselves as Lord and Lady, though that might have been a ruse in order to gain access to the royal family of Whitestone. At some point in his life (prior to arriving in Whitestone), Sylas became a vampire. Delilah herself was a necromantic wizard, having studied in part at the Alabaster Lyceum in Emon, indicating that she spent time in or might have originally come from some portion of Tal'Dorei.

During the Critical Role Campaign Wrap-Up, Matthew Mercer revealed the true origins of the Briarwoods. Originally, the Briarwoods were not nobles in the Dwendalian Empire, but they did have some renown and enough powerful connections to maintain a comfortable life in Wildemount. Delilah was a lesser mage, working with an academy of arcane studies in Wildemount. Then Sylas, her husband, got sick. No one could find a cure for his disease, so Delilah set out to find one. Though she was successful in finding a cure, she returned too late, and Sylas had passed. Delilah was so distraught by Sylas's death that she began delving further into meditation and her magic, trying to find something to stop Sylas from dying (even though Sylas was already deceased). One day, she was screaming her frustration and fury into the Astral Sea, and a voice whispered back: "I can help you." Delilah didn't know it at the time, but the voice belonged to Vecna. The whispers then started to come to her in her dreams, giving her elements of information. In her grief, Delilah followed these instructions blindly and was eventually led to one of Vecna's old laboratories. The laboratory was guarded by a nameless undead servant of Vecna (who would eventually become the Death Knight, as a reward for his centuries of loyal service). Delilah discovered the Rites of Vampirism in the laboratory, but there were some key details missing. Vecna offered to supply the missing information, but qualified: "I can give you those secrets to bring your love back to life...but then, you owe me. You're mine." Delilah replied, "Whatever it takes." She was then gifted with the full Rites of Vampirism, and Sylas Briarwood was resurrected as an undead vampire. Vecna used a fraction of his own power to perform the resurrection, tying Sylas to Vecna and ensuring the couple's cooperation.

However, necromancy is outlawed in the Dwendalian Empire, and people had begun to notice Delilah had been acting weird. Upon discovering Sylas and discovering Delilah's necromancy, they were pursued and arrested. The two managed to escape, and they fled to Port Damali on the Menagerie Coast, with Dwendalian hunters in pursuit (with orders to execute the Briarwoods on-sight). In Port Damali, the Briarwoods ran into Dr. Anna Ripley, who was also fleeing Wildemount for her own reasons. Since all three were fugitives from the Dwendalian Empire, with no direction on where to go or what to do, they decided to work together. It was in Port Damali that the new allies began to hear about Whitestone.

Arrival at Whitestone
The Briarwoods, introducing themselves as "Lord and Lady Briarwood" arrived at Whitestone Castle and were welcomed as guests of the de Rolo household. The Briarwoods began to make frequent trips from Port Damali to Whitestone to build a relationship with the ruling family. The intent was to be able to catch the de Rolos with their guard down, as well as make alliances and turn some people who worked at Castle Whitestone. For the most part, the de Rolo family had intentionally cut themselves off politically from the rest of the world. As a result of their isolationism, no one would really know or care if the de Rolos went missing or died (which is what the Briarwoods were counting on). During one feast that was held in their honor, the Briarwoods' party suddenly and violently took control of the castle, killing or capturing anyone that opposed them. The de Rolos were completely gutted, as only two members from the whole family survived: thirdborn Percival and his youngest sister, Cassandra.

The Briarwoods had Percy imprisoned beneath the Whitestone dungeons, but he was later rescued by Cassandra and the two fled. The Briarwoods either were alerted during the escape or quickly found out, as their men chased down Percy and Cassandra. While Percy escaped, his sister was hit by several arrows and collapsed. Percy presumed that she died as a result of her injuries, and he continued fleeing.

Cassandra was heavily wounded, but survived, and the Briarwoods placed her in Whitestone Castle as a prisoner once more, managing to brainwash her over a period of years to believe that she was a Briarwood rather than a de Rolo and convince her to help them in their plans for dominion over Whitestone.

Rulers of Whitestone
As rulers of Whitestone, the Briarwoods promoted the followers who helped them defeat the former rulers to nobility, namely as Barons, while they themselves took up residence in Whitestone Castle. To maintain their iron rule over the people of Whitestone, as well as hide the secret of the de Rolo family murders and Sylas's vampirism, they ordered that communication with the rest of Tal'Dorei be cut off, isolating Whitestone and plunging it and its people into a era of hopelessness and hardship.

In the years following their ascension to power, they instructed that large portions of ground underneath Whitestone and Whitestone Castle be excavated to reveal the Ziggurat that lay beneath the castle. This would later be revealed as part of a long and elaborate plan to perform a dark ritual that would resurrect the god Vecna.



Letter to Emon
Having heard, close to five years after their rise to power, that suspicion was being cast on the Briarwoods and their status as Lord and Lady of Whitestone, they sent word to Sovereign Uriel Tal'Dorei III that they would like to visit Emon to open communications and establish a plan for an official trade route into Wildemount that included a bridge from Whitestone to the neighboring continent.

Through their letter, they were able to convince the Tal'Dorei Council of their sincerity concerning the plans for a bridge and a trade route, though it seems as though such an idea was merely a ruse to remove suspicion from themselves. As well, they seemingly were able to establish some sort of believable validity to their inheritance of power from the former de Rolo rulers.

An unforeseen side effect of the letter to Emon was Percy being informed of their communication with Sovereign Uriel.

Visit to Emon
After arriving in Emon, they immediately sat down for dinner with the Tal'Dorei Council (including Vox Machina). After the dinner concluded, Vax'ildan proceeded to sneak into their guest quarters, only to be caught by them. After Sylas revealed his vampiric nature, a fight broke out between the Briarwoods and Vox Machina. After a few substantial blows, they fled back to Whitestone to lick their wounds and recover. They were then put under investigation by Uriel (though no extensive investigation efforts were carried out by anyone, save Vox Machina and Seeker Assum).

Faction Members
The Briarwoods established and maintained control over Whitestone by earning loyalty and forcing obedience.
 * Sylas Briarwood:  The Lord of House Briarwood and self-proclaimed Lord of Whitestone.
 * Delilah Briarwood:  The Lady of House Briarwood and self-proclaimed Lady of Whitestone.
 * New Nobles:  Subordinates upon whom the Briarwoods conferred titles, land, and power.
 * Countess Jazna Grebin
 * Sir Kerrion Stonefell
 * Count Tylieri
 * Duke Goran Vedmire
 * Undead minions:  Sylas created vampires and vampire spawn, and Delilah created necromantic thralls.

Trivia

 * Taliesin had only told Matt that the Briarwoods came to Whitestone and murdered Percy's family. Percy didn't know anything else about them, so Taliesin didn't write anymore about them. Thus, the Briarwoods and their backstory were written by Matt.
 * The inspiration for the Briarwoods is from a ghost story Taliesin heard about in New Orleans. A rich married couple owned a house that caught fire. When the fire brigade went upstairs, they found disastrously mutilated bodies. It was a torture chamber where the people had obviously been kept alive while the mutilations were occurring. While the fire brigade was trying to figure out and process what they had found, the couple got into a coach with their surviving belongings and left the city. They were never seen or heard from again.