Grasp of Orcus
The Shadow Academy
The Shadow Academy is a vast network of thieves and assassins founded decades ago by Cane Wolfswift and Honest Bob. The two founders had a falling out when Bob refused to a finish a job involving the assassination of a nobleman’s entire family (including his young daughters). As a result, Cane had Bob ousted from the organization and seized sole control. To add insult to injury, Cane killed Bob’s wife and kidnapped his young daughter, Valya.
Over the next twenty years, Cane led the Shadow Academy to become one of the most feared and secretive criminal organizations in the world, all the while holding Valya for an ever-increasing ransom, using her to extract both money and services from Honest Bob.
The party first encountered the Shadow Academy at Worldend, where they were working with the Malveras to keep peace in the city. Later, as the party was escorting Princess Corvyre to meet her fiancee in Kandahar, Cane’s assassins kidnapped the princess and left the party at the mercy of the Imperial guard, along with Honest Bob – whom Cane had manipulated into helping him with promises of reuniting Bob with his daughter.
Later, the party surprised and captured Cane in the Inn of Exposition. Put into the custody of Tinway and Bree, Cane tricked his captors into taking him to Wanan Cross – the initiation arena for all members of the Academy – in order to investigate certain disappearances in a nearby dragonborn village.
Once there, Cane betrayed Tinway and Bree and forced them to fight for their lives in the Academy’s arena. Cane threw the blinded Valya (who had infiltrated Cane’s organization on her own) into the pit as well; encouraging her to battle these “new initiates”.
Tinway and Bree were able to convince Valya of their motives, kill off the other combatants and free themselves from the pit. After an extended chaotic battle, Tinway, Bob and Valya were able to kill Cane, Tinway delivering the coup de grace.
In the wake of Cane’s death, Honest Bob became the new leader of the Shadow Academy. Despite Bob spending most of his time adventuring with the Daytime Group, he occasionally has to leave on Shadow Academy business, which he usually does without a word to his companions. This was the case when he went to Darkstone Hall to attend King Bram Darkstone’s summit on ways to combat the menace of the demon lord invasion in the Underdark. At the summit, he met the Evening Group and, after extracting what he deemed suitable payment from them, agreed to send eight Shadow Academy thugs along on their expedition, both to provide general support and to show them the way to Mantol-Derith, a secret neutral trading post in the Underdark, where the Shadow Academy is one of four factions allowed in, and the only surface faction.