Little is known of the deadly couple prior to the events of Percy's backstory. It is known that they were previously in Wildmount, where they may have had actual noble titles. It is also known that Silas died at some point, or fell ill, at least, and was revived by Delilah through some sort of ritual involving Vecna, the lord of secrets and one of the lords of undeath. The resulting pact made between the two brought Silas back as a vampire and seemed to gift Delilah with powerful necromantic magics. They were then forced to flee Wildmount, either by the townsfolk or by the wishes of Vecna.
Some time later they would arrive in Whitestone, the ancestral home of the de Rolo family. The de Rolo's, welcoming the mysterious couple, brought them into their castle and held a feast in their honor. It was at this point that the Briarwoods violently took the castle, slaughtering or imprisoning all of the de Rolo family, their guards, and their servants.
After Percy was tortured by the Briarwoods assistant, Dr. Ripley, he eventually managed to escape them with the aid of his younger sister, Cassandra. As they ran, Percy escaped, but Cassandra was struck down by the guards, and recaptured. The Briarwoods then began their subjugation of the impressionable young de Rolo. Over the course of many years, they were able to twist her thoughts and turn her to their side, having her help them overtake the town, shut down the rebellions, and oversee the construction of an object of great power beneath the castle, the Ziggaraut.
Eventually, the Briarwoods set their sights on the rest of Tal'Dorei, and opened talks with Emon to construct a bridge. Through their brother of worship, Lord Riskel Daxio, they were able to meet with and magically charm Septum Uriel, seizing his mind. From their, they were able to move their plans for Emon, and possibly the rest of the nation forward. That is...until they met Vox Machina.
Encounter with Vox Machina
The Briarwoods first met with the adventuring group, Vox Machina during another feast held in their honor. Pre-warned of their actions in Whitestone by their trusted member, Percy, the group took actions to try and investigate them. They disguised Percival as their Rogue member, Vax'ildan, while the real Vax went invisible, and followed them up to their room following the meal. Unfortunately, the Briarwoods were able to see through the spells keeping Vax secret, and cornered him in their bedroom. After using an enchantment to paralyze him, they attempted to subjugate him, but failed. After a brief back and forth, the Briarwoods attacked.
Vax was able to escape out into the courtyard and alert the others of the danger before he was caught. Through the assistance of their allies, Seeker Assum of the Council and Lillith, a tiefling spellcaster and cousin of their friend Zhara, the group was eventually able to overpower the Briarwoods. Sensing the turn against them, the Briarwoods retreated, first to their carriage, then, when they could not escape that way, they used a teleportation circle to return to Whitestone.
Vox Machina was able to take their driver prisoner, as a source of information, but, it became clear that the royal court of Emon saw this as an attack on their allied dignitaries and Vox Machina would be treated as suspects until a proper trial could be held. As they attempted to recover and plan their next move, they were interrupted by a ghostly attack on their prisoner, clearly sent by the Briarwoods to silence him. Following this, they could put it off no longer. Vox Machina left for Whitestone.
After arriving in Whitestone, Vox Machina set up camp beneath the town's famous Sun Tree, which had been drained by the Briarwoods to a husk of its former self. While the group's druid, Keyleth, attempted and failed to revive the tree, Percy enacted a new plan. To hunt down the Briarwood's newly elected nobles and create a new rebellion within Whitestone. Through the magic of their bard, Scanlan, they were able to seem as harmless Whitestone peasants and maneuver through the town, creating dissent against the Briarwoods, and, after the group made their own assaults on three of the Briarwoods more powerful men, were able to convince the townspeople to revolt. After several harrowing battles, the people were able to topple the zombie giants Delilah had revived to maintain order, as well as an army of skeleton creatures. As such, the people moved on Castle Whitestone, creating the perfect distraction for Vox Machina to move inside themselves.
After becoming reunited with his sister, Percy and the rest of Vox Machina followed Cassandra de Rolo deeper into the Castle's tombs, eventually finding themselves in a strange new room crafted by the Briarwoods. It was then revealed this was all a trap by the Briarwoods, who sat waiting as Cassandra sprung it, imprisoning the group in a copper vat. Vax, hoping to save everyone, used a magic cloak to poof beside the Briarwoods and flipped what he thought was a release switch. Instead, this opened a pipeline and began to fill the vat with acid. Silas then took control of Vax's mind and the four of them made their way towards the Ziggaraut, deep with the Castle's chambers.
Assault on the Ziggaraut
After several failed attempts, the group was eventually able to escape, thanks to Vex'ahlia, group ranger and Vax'ildan's sister, bending the vat up and buring through the stone ceiling. Slightly burned, and down one member, the group moved after the Briarwoods. Eventually reaching the Ziggaraut, the group took various positions, hidden from the Briarwoods' sight. All except for Percy, who came forward to take them head on.
A battle broke out. The Briarwoods' allied now with Cassandra and a controlled Vax, were able to start strong, but, eventually, all their plans began to fail. Pike, the team cleric, was eventually able to bring Vax back, and Cassandra was won back over to their side. Able to separate them, the group kept their focus on Lord Briarwood, the heavier hitter. After wearing him down, Keyleth was able to cast a sunbeam off Pike's shield, engulfing the vampire in holy sunlight and reducing him to ash.
Overcome with grief, Lady Briarwood moves into the Ziggaraut. The group tries to pursue her and find her in the middle of a ritual, within a room of corpses. Vex rushes forward to try and stop and is struck down, landing, unconscious, before her. Lady Briarwood offers her blood and completes the ritual, creating a small, spinning orb of darkness. Percy, fearing a killshot might aid whatever ritual she is performing, shoots to wound and incapacitates her.
Following another battle between Vox Machina and Percy's demonic patron (long story), Cassandra tries to escape and is recaptured. Finding no real solace in vengance anymore, Percy allows his sister to deal the fatal blow on Lady Briarwood, hoping she may gain some closure from the act.
Delilah Briarwood would later return from the dead in the episode "Unfinished Business" as part of the Vecna storyline. Vox Machina find her at the second Ziggaraut in Marquet, following a lead by then former member, Scanlan Shorthalt, to investigate it. When they find her she is now leading a cult to the lord of secrets, and had even replaced one of her eyes. How she was brought back is not known, but her involvement with Vecna was probably key.
After a battle with her followers, she escaped Vox Machina through a completed portal to the Shadowfell (similar to the one she made in Whitestone). Vox Machina recovered from the fight back at Whitestone before taking the portal there into the Shadowfell to follow her. They eventually track her down to a massive tower inside a long lost city, now inhabited with cultists and the undead. Vox Machina attempt to disrupt her actions there, but are too late, as she brings the tower through to Exandria, along with Vecna himself.
Vox Machina attempt to fight her and the Whispered One in the tower, but are proven to be outmatched very quickly. The remaining members of the team are eventually forced to flee, but not before Percival is able to finally finish his revenge, killing Lady Briarwood with two shots from his new pistol.
However, even this proves to not end the Briarwoods forever. It is revealed that Vecna has been bringing them back from the dead via new vessels that their spirits may enter. They first see Lady Delilah revived and then, much later, Lord Silas.
During the final raid on Thar Amphala (moved, by Vecna, to the head of an undead titan), Vox Machina did battle with the Briarwoods once more, aided now by a fallen paladin, Arkhan. In the final battle, Vex'ahlia deals a final fatal blow to Delilah, and Silas angrily retreats. After Vox Machina defeated Vecna and saved the world, they attempted to locate Silas again, in the woods of Vasselheim, but were unable to get a precise location. His final fate is unknown.
Powers and Abilities
Lord Briarwood was brought back to life as a powerful Vampire Warrior, and has all the abilities that entails. By far, Silas's favorite move is to charm others over to his side, and have them fight for him. He performs this on King Uriel Tal'Dorei, Vax and attempts it on Grog, but finds he is unable to do so (as Grog was raging). He was also able to drain power from his opponents in two distinct ways. First, he could restore his health by drinking the blood from others (which would reduce their max HP). Second, his sword, Craven Edge, was capable of stealing the strength from those it cut, adding to Silas's own, and making his attacks more powerful. Silas was also near-immortal, only able to be killed by exposure to heavy sunlight (or, a solar beam, as used by Keyleth).
Lady Briarwood was an even more dangerous foe. She held many items that gave her resistance to magic (a ring) and to piercing attacks (a robe), as well as a Cloak of Displacer Beast that made her harder to strike. Her magics included several de-buffs and attacks, including the ability to reduce a creature's INT to 1 (making them their most primitive selves) and casting necrotic attacks. Her specialty, though, was her ability to revive the dead as her hapless minions, capable of bringing whole armies back to life. This, plus her knowledge of even darker magics, made her a spectacularly dangerous opponent.