The week that followed was one of patient routine. On Sunday and Wednesday, Theodorus and Demetrios attended the Divine Liturgy once again. They spoke to no one, stayed late in quiet prayer, and shared a few brief, respectful words with Metropolitan Damianus before departing. The remaining daylight hours were spent as ghosts in the marketplace, observing, listening. In the evenings, they haunted the city’s three respectable inns, connecting names to roles, roles to faces, and faces to vulnerabilities.
By the following Friday, they had their diagnosis of the state of the Principality, and it was grim.
The Theodoran economy was a fundamentally agrarian system, built for survival rather than commercial expansion. Its foundation rested on the agricultural output of its few fertile, mountain-protected valleys where they harvested grain, bred hardy sheep and goats, and most importantly, produced high-quality wine that served as their primary export. This agrarian base gave the principality a degree of self-sufficiency, but it was crippled by its severely restricted access to the sea.
The rival Republic of Genoa controlled a near-monopoly on Black Sea maritime trade, forcing Theodoran merchants to either pay high tariffs in rival ports or rely on their own less secure port of Kalamita. The situation had recently deteriorated with Thedoro’s main trading vessels having been run aground by pirates, severely limiting their naval projection and trade capabilities.
That the Crimeans had thus far honoured their truce had been a small miracle, one that was starting to run out. Their estate hadn’t been the only one recently raided. A wool caravan making the trek from Suyren to Funa had also been robbed, swearing it was the work of nomads. The price of commodities was steadily rising as merchants started hoarding essential goods, fearing the markings on the horizon.
That night, Demetrios and Theodorus had finished discussing the information they’d gathered that day, the inn’s sounds muted by the intensity of the conversation. “Tonight marks exactly one week since we’ve arrived in this beautifully deceased city, Demetrios. You’ve seen the symptoms as well as I. The Principality is a body living on borrowed time.”
“Aye, my Lord.” Demetrios nodded his grim assent. “The signs are not good.”
“The signs are an invitation,” Theodorus countered, his eyes glinting in the candlelight. “We have gathered the intelligence. We have chosen our targets. Tomorrow, we go on the offensive.”
Their chosen battlefield was not the house of God, but a decadent tavern. To approach even a low-status noble at the liturgy was too risky; their fragile reputation was a tender shoot they could not afford to trample, but had to water carefully and patiently. If their performance of piety was a long-term strategic investment, this next move would be a tactical pounce.
The prey in question was a boisterous guard sergeant named Nikolaos, a man whose loud boasts and love for the drink made him a fixture at their inn. He often boasted of his excellent relationship with his senior official, even bringing him along on occasion to share drinks. Although Theodorus and Demetrios had noted that the sergeant's volume would drop considerably, his boasts replaced by a strained sobriety, whenever the captain actually joined his table.
He had a channel of information to his superior, a loose tongue when under the influence, and was easily manipulated. In other words, he was the perfect victim.
That day’s search through the market was no longer for general information, but for a specific weapon. Their weapons supplier was near the market’s western edge, his cart a small fortress of oak casks. Demetrios had recognized the merchant at once a few days prior, a man whose dealings with House Sideris went back years.
“Master Petros,” Demetrios called out.
The merchant, a portly man with a wine-stained apron, turned. His face broke into a wide smile. “Demetrios! What are you doing here in the capital? And… by the saints, is that one of Lord Konstantinos’s boys?”
“Theodorus Sideris,” Theodorus confirmed with a nod as they approached.
“A true honor, my lord,” Petros said, bowing deeply. “I trust your father is well?”
Theodorus’s gaze turned downwards. “My father passed into God’s keeping a fortnight ago. My brother, Lord Iohannes, now manages the estate.”
The merchant’s face fell, and he offered genuine condolences. “Then please, my lord, allow me to honor your father’s memory. Any cask you wish, a gift to his son.”
“A generous offer, Master Petro, thank you, but what I have need of is your expertise,” Theodorus replied, his gaze calculating. “I require a specific vintage. The sweetest you have from our lands.” He smiled faintly.
The merchant stroked his beard, lost in thought, “A sweet one? Ah! I have just the thing.” He tapped a specific, smaller cask. “From two summers ago. A good, hot year. The grapes were like honey.” He drew a small amount into a cup for Demetrios, who swirled the dark red liquid like an expert wine connoisseur, held it to his nose, and then took a thoughtful sip. His eyes closed for a moment before he gave a slow, deeply satisfied nod.
“That one, then,” Theodorus said, his decision made. As they concluded the transaction, Theodorus paid in full, surprising the merchant who initially refused the payment. “ For your expertise.” Theodorus insisted. “And you can be sure I will tell my brother that your palate remains as sharp as ever.”
The merchant beamed, bowing low. For Master Petras, he had secured not just a profitable sale but also the continuation of future business. For Theodorus, he had ensured House Sideris’s continued relationship with an honest, humble merchant.
Later that night, Nikolaos arrived at the inn, loud and already flushed with drink. He and his fellow guards caused a stir, his boasts growing with every cup of ale. He claimed to have bested a Captain Perikles in a duel that morning. At first, it was a clever parry; an hour later, it was a dramatic disarm; by the seventh cup, he was claiming to have magnanimously spared the captain’s life.
Eventually, his drinking partners, more sober and weary of his antics, excused themselves to prepare for the morning shift. Nikolaos declared he’d stay for one more, and as he ambled toward the innkeeper, Theodorus, sitting quietly at a nearby table, made his move.
“Friend,” he said, his voice just loud enough to be heard. “Forgive my intrusion, but is it true you bested
the
Captain Perikles? They say he is a devil with a sword.” Theodorus mouthed a rumour he’d heard from some fresh, sullen recruits. Although he didn’t think they were calling Perikles a master swordsman when they made the comparison.
The sergeant puffed out his chest, pleased to have a new audience. “Aye, that he is,” Nikolaos slurred, having no trouble embellishing his opponent’s skill to make his own victory seem greater. “A tough fight. But skill won the day.”
“I heard,” Theodorus leaned in conspiratorially, “that you caught him with the Boar’s Tusk counter. Is that true?”
Nikolaos blinked, trying to place the name of the maneuver. “The… aye! The Boar’s Tusk! A difficult move for most, but…” He shrugged with false modesty, “…not for some.”
“You must tell me of it, I insist.” Theodorus gestured to the empty seat at his table.
“I would, boy, but I’ve a watch in the mornin’,” Nikolaos said, already turning away. “Was just gettin’ one for the road.”
“A moment, sergeant,” Theodorus said smoothly. “I find myself with a cask of fine, sweet wine from my vineyard, and not nearly enough room in me to drink it all. It would be a shame to let it sit. Perhaps you'd do me the honour of sharing a cup with me.”
Nikolaos stopped. “
Your
wine? Who are you, boy? A merchant?”
“Theodorus Sideris. I am here to petition for a commission in the Prince’s army, but I confess my own swordplay is lacking. Yours, however, sounds truly masterful."
Nikolaos didn’t have to be sober to recognize an opportunity. An aspiring officer, a noble, and free, high-quality wine. It was just one cup. What harm could it do?
Hours later, in the dead of night, they half-carried, half-dragged a completely insensible Nikolaos to the door of his small home.
“Here is your husband,” Demetrios announced distastefully as he brusquely disposed of the sergeant's body to his wife, who had just opened the door.
She sighed, a sound of profound weariness, and took her husband’s weight with an ease that spoke of long practice. She deposited him onto a straw bed like a sack of potatoes, mumbling curses under her breath. Theodorus took the opportunity to step forward and place the half-empty wine cask on her table.
“A gift,” he said quietly, “For your trouble.”
If their first contact, Sergeant Nikolaos, was a loud and theatrical affair, the ones that followed were cultivated with the quiet precision of a master gardener. Theodorus's approaches would always start in the same vein: he would start a seemingly innocuous conversation with an overworked junior scribe, with the flamboyant town crier, with the prideful stablemaster - creatures who frequented Mangup’s various inns and marketplaces. When the opportunity presented itself, Theodorus would come prepared: A brand new swan feather quill, a fashionable burgundy hat, an artful horse stattuette. Each gift was small, tailored, and offered with a disarming sincerity that built a bridge of rapport. The currency of his operation was not coin, but thoughtfulness.
Patience was his greatest ally. His questions were never direct, the encounters always seemed accidental, the gifts ‘lucky coincidences’. Each new contact offered a thread to another - a new name, a new face, a new role, a new vulnerability - a new target. In this way, Theodorus's intelligence network grew in a beautiful and self-perpetuating cycle.
Demetrios, after watching Theodorus work, took to the craft as if born to it, learning prodigiously fast. They soon established a natural division of labor: Theodorus was the hawk, cultivating high-reaching contacts among the junior scribes, guard sergeants, and important courtiers. Demetrios was the mole, laying the foundations of their network among the lowly stablehands, the maids, and the fishmongers.
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Their partnership was deadly. By the middle of their third week in the capital, the web they had so carefully spun had caught their biggest prey yet. A person of singular interest: a young noble named Zeno Makris.
He came from a minor branch offshoot from the prominent Makris House, sharing their name, but not their wealth or prestige. He had a reputation for being diligent, industrious, and unfailingly respectful to everyone, from high officials to the lowest scullery maid. Most crucially, however, he was the only personal aide to the Megas Doux who had achieved his position by merit, not nepotism.
He was approachable. He was competent. He had the ear of the second most powerful man in the Principality. And, to Theodorus, he was the key.
The air in the common room was stale with the lingering smells of boiled cabbage and damp wool. Demetrios leaned across their scarred wooden table, his voice a low, frustrated murmur that barely carried over the snores of a nearby merchant.
“The stablehands say he has never once wagered on the races. Not a single copper folle.” Demetrios shared the news from his latest reconnaissance.
“And our good friend, Sergeant Nikolaos,” Theodorus began, a faint, wine-fueled smirk touching his lips. “Confirms it. Zeno Makris doesn’t drink, play cards, or bet on dice. Hells, the man has never once been late for a roll call.” Demetrios’s expression soured at the name. He’d never gotten over how the Sergeant had expelled his dinner all over his precious boots that night.
“Not even an amorous rumour, or a fellow officer he got on the bad side of. My Lord, the man is a saint. He has no cracks. No vulnerabilities. I am beginning to think he isn’t real.”
“You are decisively wrong, Demetrios,” Theodorus swirled the water in his cup with a dramatic flourish. ”And yet you are unnerringly correct.” He’d had more than a little wine to get the information he needed out of the sergeant, and was starting to feel its effects.
“How so?” Demetrios sighed, clearly in no mood for riddles.
“He is real, but he isn’t.” Theodorus downed his cup in one go, slamming it back onto their table. “The real Zeno Makris is the seed at the core, but all we’ve tasted is the sweet fruit he has grown around it.”
Demetrios merely raised an eyebrow.
“He has crafted an image of unimpeachable piety, unwavering loyalty, and profound humility, wouldn’t you say?” Theodorus asked with a half-lidded smile.
“You mean?”
“Yes. This Zeno Makris is playing the same game we do. And
that
is his weakness.”
“In what way?” Demetrios asked, now much more interested.
“It makes him predictable. He thinks like we do.”
“That is a sword that cuts both ways, my Lord. If he is as astute as you believe, he will see our own performance for what it is.”
“Let him. That is to our advantage. This isn’t a game that needs a winner and a loser to be played.” Theodorus’s eyes narrowed with a dangerous clarity, his drunkenness suddenly vanished. “We just need to show him that playing the game with us is a win for him.”
A moment of silence passed between them, the quiet hum of the inn a backdrop to their spinning thoughts. “This is all well and good,” Demetrios finally said, ever the pragmatist. “But how are we certain? What if he is simply… a good man? I am told they exist.”
“Because after Sergeant Nikolaos passed out, Captain Athanasios-”
“Athanasios? Nikolaos’s superior?”
“-Admitted that Zeno's diligence is almost supernatural. He told me Zeno often ‘helps’ review the equipment manifests for other patrols. A few times, he has found minor discrepancies - a shortage of rations, improperly cured waterskins - and ed them. Curiously, however, his own patrols never any problems whatsoever. This Zeno is sabotaging his rivals, and no one suspects a thing.”
Demetrios stared for a long moment, then a slow, deep chuckle rumbled in his chest. Theodorus felt his face flush, the wine-warmth turning to a darker shade of embarrassment.
“So,” the old servant said, a wide grin spreading across his face. “Your grand, infallible theory was in fact based upon a single damning detail you spent the evening getting two city guards drunk for?”
“Of course,” Theodorus mumbled, rubbing his temples. “I wouldn’t get this drunk for nothing.”
Demetrios laughed again, a warm, genuine sound that cut through the tavern’s gloom and rang painfully inside Theodorus’s ears. He could feel a headache coming on despite his best efforts. He was not looking forward to the morning.
That Saturday’s Liturgy was not a pious demonstration; it was a battlefield. Demetrios stood like a humble stone, his gaze missing nothing. Theodorus, on the other hand, had to wage a silent war just to maintain a sober disposition, the thick clouds of incense a trial for his aching head.
Their religious ritual continued unabated. They prayed, offered a respectful word to the Metropolitan, and lingered as the congregation thinned. Their target, Zeno Makris, executed a similarly flawless routine, his posture the very epitome of piety as he remained kneeling long after the final blessing.
The moment came. Instead of retreating to a quiet corner with Demetrios as was usual, Theodorus moved with quiet purpose, kneeling in a pew that placed him in Zeno’s direct periphery. It was a subtle intrusion, a deliberate shift in the room’s silent grammar. One he’d seen used by other nobles in their silent power games. He recited his morning prayers, the verses now a familiar cadence he knew by heart, then rose, crossed himself, and walked out into the sunlit courtyard without a backward glance.
Not once throughout the interaction did either of the men so much as look at each other, but Theodorus felt a cold certainty that the message had been received. A man as meticulously ambitious as Zeno could not resist the curiosity of what a minor frontier noble, barely a fortnight in the capital, could possibly want with him. And, most importantly, how he was already fluent in the high court’s silent language.
As expected, Zeno emerged from the cathedral moments later. His gaze swept the courtyard, not with haste, but with the calm, methodical precision of a surveyor. It passed over merchants and guardsmen before landing on Theodorus, who stood apart from the crowd near the main thoroughfare. For a single, charged second, their eyes locked. Everything was conveyed in that look:
Yes. I want to talk.
Theodorus turned and walked, leading them away from the heart of Mangup, his path winding from the bustling main arteries to the quieter, less-traveled veins of the city. The sounds of commerce and conversation faded, replaced by the wind whispering over the vast, green plateau that formed the capital’s wilder southern edge. He stopped in the shade of a colossal oak, its gnarled roots breaking through the earth like the knuckles of a sleeping giant, and waited.
Zeno arrived moments later, his approach silent. He stopped a respectful distance away, his posture one of relaxed grace that did nothing to hide the keen assessment in his eyes.
“Master Zeno, what a pleasant surprise.” Theodorus wore an easy smile, playing the part of the pleasantly surprised Young Master.
“Master Theodorus, truly a fortuitous encounter.” Zeno mirrored his expression expertly, playing along with the façade.
“A fine spot for contemplation, wouldn’t you say?” Theodorus said, his voice calm and easy.
“Indeed, my Lord. The world feels simpler from up here.” Zeno’s reply was just as smooth, a perfect parry. They were two actors acknowledging the stage.
“It is good to escape the city’s pressures.” Theodorus gestured to the two pewter cups and wineskin he had prepared. “I had planned to drink alone,” A blatant lie. “But I feel a divine hand behind our meeting. Please, join me.”
Zeno offered a small, apologetic smile, a flawless mask of polite regret. “You are gracious, my lord, but I do not partake in alcoholic beverages. I find they cloud the mind.”
“I know.” Theodorus nodded, his expression unchanging. He watched as Zeno’s eyes narrowed almost imperceptibly. The game was afoot. “This is not wine.” He poured a fragrant, milky liquid into a cup. “Posset. With cinnamon and mint. I find it restorative.” He held the cup out. “I would value your opinion.”
Zeno’s composure didn’t waver. He closed the distance and accepted the cup with a fluid, graceful movement. “It is an honor to be served by you directly. But does your man, Demetrios, not attend you?”
The counter-move landed perfectly. Zeno had also done his homework. Which was perhaps more impressive considering he hadn’t prepared for this meeting.
“Demetrios has returned to our inn,” Theodorus said, gesturing vaguely toward the city. “I prefer to come here alone. To be with my thoughts.”
“And which inn would that be?” It was a subtle probe, testing for hostility. An enemy does not share his base camp.
“The High Peak, near the northern walls. Have you heard of it?” Theodorus answered without hesitation. At his open reply, Zeno’s shoulders relaxed a fraction, a barely visible shift.
“My fellow officers speak well of it, though I am afraid I cannot comment personally as I don’t partake in such activities,” Zeno took a slow sip of the posset, his eyes never leaving Theodorus. “As I’m sure you’re well aware.” Theodorus nodded, seeing no need to deny it.
“What brings the third son of the Sideris family to Mangup?” Zeno asked, getting to the heart of the matter. The necessary groundwork had been laid. It was time to get down to business.
“My father, Lord Konstantinos, has passed into God’s keeping,” Theodorus recited the line with practiced sobriety.
“A great loss for the Principality. My condolences.” Zeno's answer was similarly rote.
“His death has set my path,” Theodorus continued. “I have come to Mangup to petition for a commission in the Prince’s army. I wish to become an officer, to defend our lands as he did.” He let a flash of emotion, something raw and righteous, enter his voice. “To ensure no other son must endure what I have.”
Zeno watched the performance with an unblinking gaze, utterly unmoved by the performance. Pretty words would not move him, it seemed. He inclined his head in false respect. “A worthy calling. You have petitioned the Megas Doux for an audience?”
“I have.” Theodorus took a slow sip of his posset, his eyes holding Zeno’s over the rim of the cup.
“I am to be granted the honor this coming Friday.”
Zeno’s mask of pleasantry slipped for the first time, a flicker of genuine surprise in his eyes. “Friday? I remember your presence at the Liturgy three weeks past. When did you put forward your petition?”
“On that very same day,” Theodorus said, a bitter, lopsided smile touching his lips.
“I see,” The implication was clear. “And you suspect why?”
“That, I’m afraid, I cannot say.” Theodorus said firmly, drawing the line in the sand on how much information he would provide. Zeno raised a hand in acquiescence to the gesture.
“So you see my predicament,” Theodorus continued.
“I do, my Lord. But I am unsure as to how I would be able to help.” Zeno said, all but asking what Theodorus wanted from him.
“You serve the Megas Doux. You know the man, not just the title. His moods, his methods. I wish to be prepared. To make a good first impression, that is all.”
Zeno’s lips curved into a wry, knowing smile. “And to, perhaps, have a favorable word put in on your behalf?”
“If the opportunity presented itself,” Theodorus conceded smoothly.
The pretense vanished entirely. Zeno set his cup down on the gnarled oak root beside him, his gaze turning to sharp, polished steel. “You have been very clear about what you need from me, Lord Theodorus. Now tell me. What is it that I might need from you?”
“Nothing,” Theodorus replied.
The word hung in the quiet air between them. Zeno let out a short, dry huff of a laugh, devoid of humor. “Forgive me, my Lord, if that does not seem like a favourable business deal to me.”
“That is because I did not come to you to suggest a business proposition, but to offer the start of a mutually beneficial understanding.” Theodorus countered, his voice low and steady. “I have nothing to give you today, Master Zeno, because I have nothing you would truly value. So I will offer you something far more valuable: a debt. Help me now, and I will owe you a favor. A marker you can call in at a time of your choosing. It is a debt whose value will only grow. It is an investment.”
“And how do I know there will be a return on this particular investment?”
“Because I will not remain an ignoble pawn in this game for much longer.”
“You speak of your future as if it were a foregone conclusion.” Zeno’s skepticism was a palpable force.
“It is,” Theodorus stated with an absolute conviction born from the centuries of advanced knowledge he carried over from his time. “Consider this, Master Zeno. I have been in this city for only a few short weeks, but I already know the pirates that ran our ships aground were likely Genoese proxies and that the recent Crimean raids are a political ploy to pressure the Prince into paying a higher tribute.”
He leaned back, letting his words settle. Zeno was utterly still, his face a mask of stone, but his eyes were sharp, polished steel. Theodorus hadn’t just shown him ambition; he’d shown him a terrifyingly astute mind.
“That is dangerous information for the third son of a disgraced noble to hold,” Zeno said quietly, his words heavy with implication. "Especially one with genealogical ties to a Tatar slave."
“I am not a spy, or we would not be having this conversation,” Theodorus replied with righteous authority, the sincerity in his voice absolute. “My offer is sincere, as are my intentions. You can take the deal, or you can forget our 'fortuitous encounter' ever happened, Master Zeno. The choice is yours.”
A long silence stretched between them, broken only by the rustle of the oak leaves above. Zeno’s mind, a machine of calculation, weighed the odds. This boy was either a madman or a prodigy. He was frail, young, and heir to a tarnished name. But the instincts that had guided Zeno’s own quiet, meteoric rise were screaming at him. Telling him this boy was special. Whether for better or for worse, he could not yet tell.
A decision had to be made. And as Zeno looked into Theodorus's fearless eyes, he knew which one he’d make.
“It is done.” Theodorus announced. He found Demetrios in the shadows of a pre-arranged side street.
“He accepted?” Demetrios asked. He had spent the past hour in a state of perpetual anxiety.
“Of course.” Theodorus answered as if there had been no doubt.
“I admire your confidence, my Lord.” Demetrios let out a breath he did not know he was holding.
“It’s not confidence, Demetrios. It’s knowledge. I knew he would agree because he thinks like me. He recognizes a valuable asset when he sees one.”
“But now we must deal with the Megas Doux, not your long-lost twin." Demetrios’s relief was short-lived, replaced by anxiety once again. "He is a different beast altogether.”
“I know,” Theodorus looked toward the imposing silhouette of the castle keep, a dark shadow against the evening sky. “But we have just been given the keys to his cage.”
A grim determination settled over them. The first battle was won, but the true test now loomed. As they walked back toward the inn, the weight of the work to come was a heavy, unspoken presence between them.
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