Delilah Briarwood

Delilah Briarwood, or Lady Briarwood, was a powerful human wizard—a necromancer, according to Cassandra. She and her husband, Lord Sylas Briarwood, slaughtered the entire de Rolo family (except for Percy and Cassandra), then seized Whitestone for a dark ritual involving Vecna.

About five years after Whitestone fell to the Briarwoods, Percy returned with Vox Machina to claim revenge. They were able to foment a citizens' rebellion, disrupt the Briarwoods' ritual, kill Sylas, and finally kill a grieving Delilah.

However, she was revealed to be alive in Marquet over a year later, after completing a second (or possibly third) ziggurat ritual. She was killed for a second time during the fight against Vecna, after his resurrection atop Entropis.

After coming back to life a third time, Delilah was killed by Vox Machina after they returned to Thar Amphala from the Feywild.

Appearance
When Vox Machina first met her, Delilah was a beautiful woman with dark auburn hair, pulled up into a tight braided bun. With gloves on her feminine hands, she wore a blue and black gown that had a long, billowing skirt that tapered up to be form-fitting, wrapping up her neck nearly to her jaw.

Background

 * &rarr; See also:  Briarwoods

Delilah Briarwood trained briefly at the Alabaster Lyceum in Emon.

It is briefly mentioned that the Briarwoods had been in Emon for about a week on a diplomatic mission to discuss the establishment of the official trade route through the northeast with Sovereign Uriel.

Asum informs Vox Machina that the Briarwoods are en route to Emon as, in celebration of the agreed-upon construction of a grand bridge across the Shearing Channel to the eastern continent of Wynandir, a dinner is being held here within a week.

The Briarwoods hold a dinner celebrating the agreed upon venture of the construction of a grand bridge across the Shearing Channel to the eastern continent of Wynandi with Uriel and the Council members (including an invite to Vox Machina)

Discussion takes place of the intricate details of the trade route between Wildemount and Tal'Dorei before the conversation segues into conversation about the Briarwoods history in Whitestone.

Delilah spins a tale of how they both met the De Rolo family after taking them into their home during a terrible storm while the family had been on holiday and had been intending to meet with the noble family to discuss pursuing the venture as a joint trade before disease took the family. With the death of the entire family and no heir left to inherit the city it had been to their surprise that the mantle had been passed onto them to spearhead the venture and take over Whitestone in their stead.

Conversation moves on to discuss Vox Machina's adventures briefly before Scanlan interjects asking about the disease that had taken the De Rolos. Sylas states that they had only been given the information but a month or two after the family had passed away much to the confusion of Keyleth wondering why they had not been afraid to enter the castle after the disease had swept through. Sylas reassures the druid that they had sent their best clerics to rid of any existing possible lingering disease, and to make sure to remove any corpses or bodies that may contain it before they moved in.

Eventually the couple retires to their rooms leaving the group to their own devices.

They are then alerted to Vax'ildan entering their quarters not a few moments later under the guise of being a guard. As the rogue tries to talk his way out of the room as he backs up to the door, Delilah questions his identity citing they had just been to dinner with someone who looked uncannily like Vax.

Delilah smirks and begins incantating under her breath just as Vax tries to take off, managing to capture him with a Hold Person spell, mid retreat. Vax continues to try to talk his way out of the situation even as Delilah approaches him and Sylas flanks him from the other side.

Delilah berates Vax for trying to flee when she simply wanted to ask him some questions in their private quarters just as Sylas slams a hand down on Vax citing not to worry and he looked delicious.

Sylas Briarwood
Delilah was married to Sylas Briarwood. Their marriage is portrayed as deeply loving; when Sylas is killed by Pike, Delilah is immediately distraught and yells, "You can't! I broke the world for us!".

Cassandra de Rolo
Delilah and Sylas did not kill Cassandra when they murdered the rest of the de Rolo family, but instead kept her as a pawn in maintaining peace in Whitestone. Over time, Cassandra developed a (somewhat Stockholm Syndrome-esque) loyalty to her captors and began to do their bidding. She helped them quash one rebellion attempt prior to Vox Machina's arrival and willingly betrayed her brother to the Briarwoods on his return.

1st-level

 * Shield

2nd-level

 * Hold Person
 * Misty Step

3rd-level

 * Dispel Magic
 * Haste

4th-level

 * Blight
 * Dimension Door

6th-level

 * Disintegrate

7th-level

 * Finger of Death

8th-level

 * Clone
 * Feeblemind
 * Power Word Stun

9th-level

 * Prismatic Wall

Notable Items

 * Eye of Vecna (removed from her second corpse by Vox Machina, later destroyed by Pelor)

Trivia

 * Laura Bailey dressed as Lady Briarwood during, which aired the week before Halloween 2016.
 * In the Critical Role Major Arcana Tarot Card Set, she along with her husband, Sylas, represent VI - The Lovers.
 * Delilah has been killed three times so far, all by a de Rolo; once by Cassandra in, once by Percy in , and once by Vex in.