Olo Moonshadow

Olo Moonshadow, or Olo Shadow, is the charismatic and flirtatious debutant of the group. Although he is often seen plying his wiles in the hope of seducing a fair maiden, his prowess in combat is unparalleled. Olo knowingly brought the "Three Companions" together as he shared connections with both Thuldus and Sauriv from past adventures and encounters.

Life as an Orphan
Olomorn Moonshadow, or Olo Shadow on the streets of Waterdeep, was an urchin. His parents were either dead or missing which left the raising of Olo to the ramshackle community of other hopeless wanderers and urchins until he was old enough to fend for himself. He wandered the streets of the great city and begged, borrowed, or stole anything he could get his hands on to make ends meet. This life of vagrancy and destitution did not hold a fortuitous outlook for the young boy but his fortunes suddenly changed on his sixth nameday.

Rags to Riches
One day, Olo found himself cornered in a back alley by some well dressed and heavily armed house guards, thinking his time was up, he prepared himself to fight for his life, not giving these brutes the satisfaction of the boy begging for his life. Curiously, his assailants simply held him there until one of the most beautiful women Olo had ever seen arrived. She introduced herself as Sylyra Eildi and offered him food, drink and a warm place to rest his head. Olo was weary at first, generosity of this kind of uncommon; rather unfathomable. It was almost dangerous to accept; however, a full belly and a warm bed are enough to convince enough the weariest of urchins to consider the risk. Olo came into her estate and was surrounded by luxury and wealth unlike anything he had seen before.

A Childhood Unlike No Other
Sylyra was a cold woman, not showing an iota of compassion or love for Olo. Were he is blood child he may have taken the slight more personally but he had been raised by the streets – Olo was tough and he shook of his patron’s disdain. Although she was cold to Olo, she was not necessarily unkind. Olo was taught to read and write. He was taught etiquette at balls and fieldcraft in battle. Sylyra, a warmaiden in her own right, shared with Olo her own martial skills and the young boy rapidly developed into a skilled warrior. His lean and gaunt physique rapidly transformed into hardened muscle. The other eleven handmaidens and courtiers within her estate rapidly became quite interested in the boy prodigy.

In Service to the Warmaiden
Olo, now a capable fighter, journeyed beyond the estate and offered his skills to other nobles of Sylyra’s estate. A Head Librarian of Candlekeep who often frequented Sylyra’s estate requested their aid in dispatching some bandits who were harrying pilgrims in their journey to the Fortress Library. Olo was dispatched, of his own volition, and met up with a young lizardfolk named Sauriv to destroy their bandits in their camp.

Dreams & Demise
It was in his peak that the dreams came. First they were subtle. A glimpse of a figure in a deep sleep or the echoes of a woman’s voice. Then the nightmares began to manifest. A shadowy figure. Sigils pulsing and their curling script being branded into his mind. He journeyed to Candlekeep and consulted with a younger cleric named Thuldus, who identified them as primordial and directed him to some tomes which could help decipher the ruins. It was while he was in Candlekeep that he received the news. Sylyra Eildi, his matron and benefactor – had died. The surgeons said it was of natural causes but something about the circumstances bothered Olo. He made for Waterdeep with great haste to investigate. As he raced along the high road, a voice called out to him:

"“You are he that was promised to me. The witch’s sorcery cannot protect you any longer my child. Seek the Yawning Portal. It is there that my story with you begins.”" Olo was stricken by fear but the words remained clear in his head as if they had just been spoken. He felt a sickening compulsion as he tried to pull away from the road to Waterdeep and knew deep down there was no other way. Resolved and afraid, he set off to Waterdeep and the Yawning Portal Inn.