Milo Blackbarrel
SHADOWMASTERS DOSSIER
Name: Milo
Affiliation: Shadowmasters of Telflamm
Occupation: Rogue, Guild Operative
Faith: Shar, Mistress of the Night
Status: Active, Senior Operative
I. Origins
Milo was born at Trail’s End, where the roads thinned into wilderness and the world felt small and self-contained. His earliest memories were of wind over tall grass and the steady comfort of his parents’ presence.
After only a few short years, his family relocated to Ilmwatch, seeking steadier prospects and stronger ties to trade.
Ilmwatch fostered discipline but could not contain ambition. By fourteen, Milo had grown restless with the predictable rhythms of village life. Drawn to opportunity and independence, he left his parents behind and traveled east to Telflamm — a city of commerce, coin, and shadowed dealings. His departure was not merely geographic; it marked the beginning of a self-determined life.
II. Loss and Conversion
At eighteen, Milo received word of his father’s death from illness. In the aftermath, his mother devoted herself to Selûne, the Moonmaiden, seeking solace in faith.
Milo interpreted her devotion not as strength, but surrender.
Where she turned toward silver light and prayer, he turned inward — toward anger and defiance. Rejecting her path, he pledged himself to Shar, Mistress of the Night. What began as rebellion matured into conviction. Shar’s doctrines of secrecy, loss, and hidden strength resonated with the grief he refused to express openly.
This spiritual divergence marked a permanent fracture in his past — and a defining moment in his future.
III. Induction into the Shadowmasters
By the age of twenty, Milo’s devotion and aptitude brought him into the ranks of the Shadowmasters of Telflamm.
Within the guild, he demonstrated patience, subtlety, and calculated ambition. Over the course of a decade, he honed his craft:
Infiltration and silent entry
Intelligence gathering
Social manipulation and manufactured trust
Lockpicking and arcane countermeasures
Covert negotiation
He evolved from a runaway youth into a disciplined and precise operative. Reputation replaced recklessness; restraint replaced reaction.
IV. Evereska Assignment
After ten years of loyal service, Milo was entrusted with a diplomatic and covert mission to Evereska, specifically to the thieves’ guild operating from Moondark Hill.
Official Purpose:
To exchange information, techniques, and magical practices between allied organizations.
Unofficial Objective:
To evaluate, acquire, and if possible recruit the guild’s most promising talents and methods for the benefit of the Shadowmasters.
Milo remained embedded for five years.
During this period, he developed a close relationship with a gifted young thief of notable potential. Recognizing both their skill and influence, he attempted to guide them toward allegiance with Telflamm. Despite careful effort, their loyalty held firm.
While recruitment failed, the partnership yielded something else: shared pursuit of rumor and legend. Together, they investigated whispers of one of Mask’s legendary longswords — an artifact said to carry the favor of the Lord of Shadows. Whether the blade was discovered or remains lost to rumor is a matter open to campaign development.
Ultimately, Milo chose duty over sentiment and returned to Telflamm.
V. Return and Advancement
Milo’s return marked a transition. He was no longer merely a capable operative; he was a seasoned strategist within the Shadowmasters. His years abroad elevated his authority and positioned him for greater influence within guild operations.
Shortly after his return, he encountered Navarra Stayanoga.
Navarra arrived in Telflamm seeking to sell jhuild — valuable cargo subject to heavy tariffs and duties. Rather than submit to official channels, she pursued distribution through Shadowmaster networks.
Milo recognized in her ambition, calculation, and willingness to assume risk. Their association began as pragmatic negotiation — profit, leverage, and mutual advantage. Yet in Telflamm, business alliances often evolve into something more intricate.
Whether Navarra represents opportunity, liability, or transformation remains to be seen.
VI. Psychological Profile
Highly self-directed; distrustful of overt piety
Values subtle power over public recognition
Motivated by control, influence, and independence
Carries unresolved grief masked by discipline
Prone to long-term strategic thinking rather than impulsive action
VII. Active Narrative Threads (For DM Use)
Potential conflict between Shar and Selûnite interests
Political maneuvering within the Shadowmasters
Lingering connection to the Evereskan thief
The fate of Mask’s legendary longsword
Navarra Stayanoga’s smuggling operations drawing external scrutiny