Delilah Briarwood

Lady Delilah 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.

Personality
Delilah was incredibly cunning and intelligent as well as ruthless, cold, and willful. She was strategically minded and astute, clearly being the mastermind behind the Briarwood's plans in Whitestone. Despite her wicked nature she appeared to be genuinely loving, devoted, and affectionate towards her husband, willing to do anything to preserve their life together.

Background

 * &rarr; See also: Briarwoods

Delilah Briarwood trained briefly at the Alabaster Lyceum in Emon.

It was 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 informed Vox Machina that the Briarwoods were 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 was being held here within a week.

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

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

Delilah spun 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 moved on to discuss Vox Machina's adventures briefly before Scanlan interjected asking about the disease that had taken the de Rolos. Sylas stated 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 reassured 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 retired to their rooms leaving the group to their own devices.

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

Delilah smirked and began an incantation under her breath just as Vax tried to take off, managing to capture him with a Hold Person spell, mid retreat. Vax continued to try to talk his way out of the situation even as Delilah approached him and Sylas flanked him from the other side.

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

Delilah was killed by Vex'ahlia and turned into a zombie by Arkhan.

The zombified Delilah was revealed to have been beheaded during Arkhan's battle with the Death Knight.

Sylas Briarwood
Delilah was married to Sylas Briarwood. Their marriage is portrayed as deeply loving; when Sylas is killed by Keyleth, 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
 * Invisibility
 * Misty Step

3rd-level

 * Counterspell
 * 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)

Quotations

 * "Whatever it takes." (Delilah accepting Vecna's deal for the Rites of Vampirism to resurrect Sylas)
 * "NOOOOOOOO!!! I BROKE THE WORLD FOR US!!!" (Delilah screaming in horror after Sylas was destroyed by Keyleth at the Ziggurat)

Trivia

 * Laura Bailey dressed as Lady Briarwood during, which aired the week before Halloween 2016. Laura has identified Delilah as the "Anti-Vex'ahlia", and Vex (had she gone down a darker path) came very close to becoming someone very similar to Delilah.
 * 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.