Rylan Callister Character in A Time of Wolves Among Vipers | World Anvil
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Rylan Callister (RYE-lin CAL-is-ter)

Rylan Callister

Rylan Callister, spymaster of Calembar, devoted his life to gathering intelligence and foiling the sinister plots of the kingdom's enemies.

Mental characteristics

Personal history

Rylan grew up an orphan on the streets in the kingdom of Ardmay. He never knew his parents and had to rely on his wits and stealth to survive. As a young boy, Rylan was unusually observant and insightful. He quickly learned how to glean information from overheard conversations and noticed details that others missed. These skills allowed him to avoid trouble and evade the authorities.   One day, Rylan picked the pocket of a man who turned out to be the spymaster of Calembar. Impressed by the boy's deft skills, the man spared Rylan punishment and instead offered him food and shelter in exchange for putting his talents to use as a spy. Rylan eagerly accepted the offer.   Under the spymaster's mentorship, Rylan honed his innate abilities. He learned how to blend into the shadows, move with utmost secrecy, and gather valuable intelligence undetected. His humble origins made him adept at infiltrating different segments of society. Over time, Rylan proved himself a highly effective spy.   When the spymaster died, Rylan became his successor. By then, Rylan had established contacts throughout the kingdoms and accumulated a vast knowledge of inner workings within his kingdom. His proficiency in espionage made him the ideal candidate to become the spymaster.   Taking charge of the intelligence network, Rylan worked diligently to root out conspiracies and foil schemes aimed at overthrowing the kingdom. His loyalty lay with the people, not the rulers. Rylan knew that his position allowed him to protect the vulnerable and helpless - the way no one had protected him growing up. Being a spymaster enabled him to serve the greater good.


When the spymaster first took Rylan under his wing, he knew that the perceptive street orphan had immense potential as a spy. However, Rylan's lack of education could hold him back. Illiteracy would be a severe liability in intelligence work.   So along with mentoring Rylan in the arts of stealth, concealment, and gathering information, the spymaster also taught the boy to read and write. At first, these were difficult skills for Rylan to grasp. But the spymaster patiently worked with him day after day, explaining the alphabet, helping him sound out words, and guiding him to form letters with chalk on bare stone walls.   Rylan took to his reading and writing lessons with determination, spending long hours practicing. He recognized these skills would open up a world of knowledge to him that had always been out of reach. Gradually Rylan gained proficiency in deciphering the intricate symbols of written text. His penmanship became legible enough to record observations in his spy work.   The spymaster allowed Rylan access to his personal library, full of books containing wisdom gathered over decades. Rylan eagerly devoured the information available to him, reading late into the night by candlelight. The more he read about history, politics, and foreign lands, the more insightful he became as a budding spymaster.   Thanks to the patient guidance of the spymaster, Rylan transformed from a street urchin to an educated, literate young man able to serve the kingdom's intelligence needs. The spymaster's mentorship provided Rylan with the essential skills to fully embrace his future role.

Accomplishments & Achievements

In his first years as spymaster, Rylan quietly built up an extensive information network across the kingdom. He recruited and trained spies to blend into all levels of society, from peasants and merchants to nobles and clergy. Rylan soon had eyes and ears everywhere, feeding him invaluable insights.    His information networks across borders gave him leverage in diplomatic negotiations as well. Rylan helped secure vital trade routes and strategic alliances that brought prosperity to the kingdom.

Failures & Embarrassments

The first major misstep came early in Rylan's career when a covert mission went awry. He had dispatched a team of spies to infiltrate a town across the border. But the mission ended disastrously, with all of Rylan's agents captured or killed. The debacle was a crushing setback that taught Rylan a hard lesson about meticulous planning and choosing personnel wisely.   Some years later, Rylan underestimated the cunning of a visiting dignitary from a rival kingdom. Believing the diplomat was an ally, Rylan allowed him access to sensitive information. But the diplomat was actually a master spy sent to gather intelligence. By the time Rylan realized the deception, it was too late - vital state secrets had been compromised.
by Midjourney
Honorary & Occupational Titles
Black Hair


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