The Briarwoods

The Briarwoods — Lord Sylas & Lady Delilah

Lord Sylas and Lady Delilah Briarwood standing beneath the dawn-lit Sun Tree in Whitestone

“We have done unforgivable things and forgivable things both. The work is to act, today, as if the second category is the only one open to us.” — Lady Delilah Briarwood, sermon at the Sun Tree, 832 P.D.

Original Canon Identity

In Critical Role canon, Sylas and Delilah Briarwood were the vampire-and-necromancer ruling couple of Whitestone, who had usurped the de Rolo family and were attempting a ritual to summon the Whispered One. They were Vox Machina’s first major antagonists.

This World’s Truth

Sylas and Delilah were a couple from Wildemount nobility who, in their youth, did indeed dabble with the cult of the Whispered One. They left. They renounced. They walked the long road of atonement: Sylas became a paladin sworn to Pelor (the Dawnfather, who in this world chose to forgive them); Delilah became a cleric of the Raven Queen, devoted to honoring the dead they had once dishonored.

In 798 P.D., when Whitestone overthrew the tyrant Frederick de Rolo, the city’s council invited the Briarwoods — known as wandering healers and mediators — to restore order. They came. They governed for twelve years with care, replanted the Sun Tree, ran a clinic, and were genuinely loved by most of the city.

When Percival de Rolo returned in 810 P.D. with firearms and a private army, the Briarwoods led the resistance. Percival shot Sylas through the chest at the foot of the Sun Tree in 813 P.D. Sylas survived long enough to kill Pike Trickfoot — Vox Machina’s cleric — in single combat, and to crawl back to the Tree and die under it. Pelor’s blessing on his last act sanctified the Tree as it stands today.

Delilah survived. Two years later, in 812 P.D. — at the war’s last engagement — she shot Percival herself, with a single bullet, on the roof of Whitestone Castle. She has not held a firearm since.

War Role

Sylas held Whitestone’s defense during the initial Vox Machina assault, fell at the Sun Tree.
Delilah orchestrated the alliance: drew Dr. Ripley out of grief and into the war effort, opened correspondence with the Chroma Council and with Vecna, designed the trap that took Percival.

She is widely considered the war’s most important strategic mind. She does not accept the title.

Modern Day

Lady Delilah Briarwood is eighty years old in 836 P.D. and lives in Whitestone Castle as the spiritual advisor to Lady Cassandra de Rolo — Percival’s sister, the city’s current ruler, and one of Delilah’s closest friends. The two women have an arrangement that is half political, half familial: Cassandra rules, Delilah advises and runs the Sun Tree’s small temple.

Delilah:

writes letters constantly. She corresponds with every other surviving Savior, with several scholars across Exandria, and with at least one party that the PCs may turn out to be.
visits Sylas’s tomb beneath the Sun Tree at dawn every day. She speaks to him aloud. The temple’s clergy give her privacy.
keeps her old necromancer’s writing-desk in her study. She does not deny what she once was. She does not flinch from it.

She is the campaign’s most likely first major Savior NPC — a clear, gentle, dangerous woman who will see through the party’s pretenses faster than they expect, and will offer her counsel for free if asked.

Roleplay Hooks

Voice: low, warm, deliberately measured. She has a slight Wildemount accent that she has not lost in fifty years. She thinks before she speaks. She means what she speaks.
Soft spots: Sylas (always). Cassandra. The orphans of the Whitestone purges, whom she sponsored personally for years. Music — she plays the lute badly and beautifully.
Hard spots: any reference to who she once was in a tone that suggests it cancels who she is now. (She will hear it. She will not engage. She will quietly note it.)
Tells: she touches her wedding ring when she is thinking. She carries Sylas’s old holy symbol in her pocket. She has not aged faster than her years — but she sleeps badly, and on a long enough conversation, the party will notice.

Stats & Build — if combat is forced (rare)

The campaign assumes Lady Delilah is not a combat encounter. She is a moral and political force. If she is forced into combat, she will avoid it. If she cannot avoid it, she will end it quickly.

Tier 4 (level 18) effective.
Class: Cleric (Grave Domain) 12 / Wizard (Necromancy, fully renounced school — she still knows the spells, refuses to cast them) 6.
Signature gear: Sylas’s old holy symbol (Pelor), her own (the Raven Queen), a pearl-handled flintlock pistol (kept on a shelf, never carried, the bullet that killed Percival never fired).
Suggested CR: 17.
Special: she has cast Wish twice in her life — once during the war, once at Sylas’s grave the day he died. She has the resources to cast it again. She will not.