Backstory
In the latter portion of the 270s AC Calaila ran with a loose affiliation of female cutpurses and burglars in King’s Landing. Calling them a band or crew would be a stretch, but on any given night 6-12 relatively young women would gather in a particular pot shop In Flea Bottom and recount their experiences that day. In dire times they could pool resources and could also sometimes enlist each other’s help if a plot for a larger take called for more than one. There was a young blonde woman, who was a bit of a ringleader, and about 5 years older than Calaila named Olivia. Olivia was a master of deception and was a skilled thief in her own right, but lacked the cleverness of some of their peers.

One night Olivia confided in Calaila that she had adopted the robber lifestyle by choice. She is actually the “beloved niece” – to use her words – of a wealthy Lyseni merchant (Tontos Caballero) who lives in a manse just on the other side of the Hill Of Rhaenys. Time, and alcohol, has muddied the recollections of both but ultimately a plot was hatched. Olivia was to enter the home and gain the attention of her uncle and his personal guard; and while visiting unlatch a door to the courtyard. Calaila was to sneak in and empty his vault of all valuables and escape. If discovered Calaila was to charm, and if need be fight, her way out. However, Tontos seemed on guard from the start and he had his men apprehend Olivia and Calaila was nearly captured when the side door remained locked and gold cloaks closed in on her. She was able to escape, and eventually flee King’s Landing, and Olivia and Calaila did not see each other again for several years.

In-Campaign
Olivia has been in service of House Corbray for a few years. She has said that she was a traveling Septa, visiting small villages and hamlets, for a few years prior. What is known to none in her current life is that Septa Olivia spent her early years in King’s Landing as the “beloved niece” of a wealthy Lyseni merchant named Tontos Caballero and as a criminal.

In September of 282 AC two unfamiliar men entered the sept at Heart’s Home, sat, and spoke to her of politics and alliances. The more eloquent man spoke of the crone, father, and more showing him the righteousness of Robert’s cause. He made a compelling case and convinced the Kingslander to speak to Lord Lucian on his behalf. The other man then departed for the training yard, leaving Olivia and the eloquent farmer to continue conversing in hushed tones. It was then that Carsen agreed to assassinate Calaila on Olivia’s behalf, for reasons unknown to him. He did this in exchange for Olivia speaking to Lord Corbray in favor of the Jaspers’ cause.

While attending the weddings of Jon and Lysa and Eddard and Catelyn with her liege, Lord Lucian, in 283 AC Olivia spotted a familiar face. Olivia approached her old associate Calaila. Pleasantries were exchanged but the tension between them was palpable. They parted ways without incident. The morning following the festivities Olivia was nowhere to be found, she and her belongings had vanished.

After taking shelter with a group of cutpurses and robbers in Gulltown Olivia ascended the pecking order in a matter of weeks. While penning a letter one evening she heard a large group passing in the hall outside her room. She opened the door to be face-to-face with her nemesis, Calaila. Olvia reacted quickly, reaching for a dagger and stabbing her former friend. Calaila got away and a bard (who was more competent at fighting than expected) took her place. The two traded blows as fighting erupted around them. As they tide of the melee turned against her she tried to flee, first through a window and then deeper into the structure. She did not emerge after Calaila set the building ablaze.