The harbor of Pentos spread before them like a merchant's dream come true. Dozens of ships crowded the stone piers - fat-bellied cogs from Lys laden with silk and spices, sleek galleys from Myr with their bronze-beaked prows, and the distinctive red-sailed vessels of Volantis that seemed to dwarf everything around them. The air hung thick with the scent of salt water, exotic spices, and the less pleasant odors that came with any major port.
[ Quest Update: Shadows of the East ]
[ Objective: Establish a foothold in Pentos. Gather intelligence on local power structures and secure a contract for The Hidden Blade. ]
[ Reward: Increased reputation, 3 SP, 2500 exp. ]
Jon stood at The Wayfarer's bow as Kojja Mo expertly guided them toward an empty berth near the outer edge of the harbor. The Summer Islander had explained that newer companies and smaller ships were relegated to the cheaper, less secure docks - a reminder of their current station in the mercenary hierarchy.
"Two gold dragons for a moon's docking," the harbormaster informed them, a thin man with the soft look of someone who had grown wealthy from other people's work. "And one more dragon for the harbor tax."
Jon handed over the coins without complaint, though he noted how the man's eyes lingered on their purse. Word would spread quickly about the new company with money to spend. That could be useful, or dangerous.
"Garth, Sten, Willem," Jon called out as they secured the ship. "You three stay with The Wayfarer. Four-hour watches, full arms. No one boards without my permission."
"Expecting trouble, Captain?" Garth asked, already checking his bow.
"In a city where sellsword companies disappear?" Jon replied. "I'm expecting everything."
He turned to his companions. "Orbelo, Kaelo, with me. We need lodgings and information, in that order."
The streets of Pentos were a maze of wealth and squalor pressed against each other like lovers in a bed too small. Grand merchant palaces with soaring towers and golden domes stood mere blocks from ramshackle tenements where the poor crowded together in conditions that would shame a kennel.
They found suitable accommodations at The Merchant's Rest, an inn that catered to visiting traders and minor sellsword companies. The three-story building sat at the intersection of two major thoroughfares, its position allowing clear views of approaching traffic from multiple directions. The proprietor, a matronly woman named Vassa, quoted them reasonable rates for a suite of rooms that would allow them privacy.
"Food's good, wine's better, and we don't ask questions about your business," she said with a knowing smile. "Just keep the noise down and pay your bills prompt. We've housed sellswords before - some left richer, some left in pieces. Which one you'll be depends on how smart you are."
That evening, as they settled into their rooms, Jon outlined his plan. "Three days," he told Orbelo and Kaelo. "I want to know everything about this city before we start looking for work. Politics, power structures, who's feuding with whom. Most importantly, which magisters hire mercenaries and which ones have been losing companies."
"Together or separate?" Kaelo asked.
"Together. You're both strangers here - you'll attract less attention as traveling scholars than as individual investigators."
As they departed the next morning, Jon took to the streets himself. He wandered the bazaars and markets, using The Sight to gauge the city's pulse. What he saw painted a picture of a society balanced on the edge of a knife. The opulent palanquins of magisters were carried by slaves whose eyes held barely contained hatred. Beggars haunted every shadow, their numbers far greater than any healthy city should support. Guards in gleaming scale armor patrolled in groups, collecting "taxes" that looked suspiciously like bribes from merchants who paid with resigned acceptance.
The architecture itself told the story of Pentos's rise. Ancient Valyrian stonework formed the foundations of the oldest districts, their black stone walls still bearing the sigils of dragonlords who had ruled here before the Doom. Above these ancient foundations, successive generations had built layer upon layer of newer construction - Pentoshi marble, Myrish glass, Lysene tilework - creating a vertical timeline of the city's commercial conquests.
In the port district, Jon observed the careful hierarchies that governed even the loading of ships. Lysene vessels received priority berthing and the first pick of stevedores. Myrish galleys came next, their captains treated with respectful efficiency. Ships from smaller cities or independent traders waited their turn, often for days, while their goods spoiled in the hold. It was a system designed to reinforce the existing order of power among the Free Cities, with Pentos positioning itself as the indispensable middleman.
The next three days passed in careful reconnaissance. While Jon made himself visible around the inn and the nearby taverns - establishing their presence and letting word spread of a new company looking for work - his two companions disappeared into the city's underbelly of information brokers, merchant clerks, and tavern gossips.
Jon's own investigations focused on the sellsword companies currently operating in the city. He counted at least eight different groups, ranging from the Golden Company's local representatives to small bands of hedge knights seeking employment. What troubled him was how nervous they all seemed. Veteran sellswords were typically a confident lot, secure in their skills and the demand for their services. But here in Pentos, even the most experienced captains spoke in hushed tones about contracts in the Disputed Lands, and more than one refused such work outright.
On the fourth morning, Orbelo and Kaelo returned together, the scholar carrying his usual collection of notes while Kaelo bore a small but telling collection of bruises on his knuckles.
"Don't tell me you had to fight your way out of a library," Jon said dryly, noting Kaelo's condition.
"Close," Kaelo replied, flexing his hand. "Turns out some Pentoshi don't appreciate foreigners asking too many questions about their missing sellswords. Had to convince a few dock workers that our questions were purely academic."
"Define 'convince,'" Jon said, though he was already reaching for his medical supplies.
"Nothing permanent," Orbelo assured him. "Kaelo showed admirable restraint. Though I must say, watching him debate philosophy with his fists was quite educational."
"Philosophy?" Jon raised an eyebrow as he examined Kaelo's knuckles.
"The fundamental question of whether information should be freely shared or require payment in blood," Kaelo said with a grimace as Jon cleaned the cuts. "I argued for the former. Vigorously."
"And won the debate, I assume?"
"Eventually. Though Orbelo had to translate my final points - apparently my Pentoshi isn't as fluent as I thought."
Jon finished bandaging Kaelo's hand, then looked at both men seriously. "So. What have you found?"
Orbelo spread his notes across the table, his scholar's mind having processed three days' worth of observations into a clear picture of Pentos's power structure.
"Pentos is exactly what we expected," the scholar began, spreading his notes across the table in their shared room. "A city where wealth equals power, ruled over by a Prince with a council of rich magisters. But the Prince has mostly ceremonial functions - he presides over balls and feasts, gets carried around in a rich palanquin with handsome guards, and each new year deflowers two maidens - the Maid of the Sea and the Maid of the Fields - to ensure prosperity."
"Sounds like a pleasant life," Kaelo observed dryly.
"Until the city faces famine or loses a war," Orbelo continued. "Then the magisters sacrifice the Prince and slit his throat to appease the gods, before choosing a new one from the forty families. It's happened three times in the past century, always during crises that threatened the city's prosperity."
Kaelo grimaced at the thought.
Jon leaned forward. "So real power lies with the magisters."
"Exactly. There are perhaps two dozen of them with serious influence, though they're divided into factions. The traders want stability and profitable routes. The slavers - though they call themselves 'labor contractors' now - want expansion into new markets. The old families want to preserve their traditional privileges. But there's a fourth faction that's been gaining influence - the 'New Money' magisters who've made their fortunes in the past generation through innovative trades or successful speculation."
"And which ones hire sellsword companies?"
Orbelo smiled grimly. "That's where it gets interesting. Three companies have vanished in the past year, all working for different magisters. But there's a pattern - they all took contracts in the Disputed Lands, guarding trade routes or settling territorial disputes. The Crimson Hawks, two hundred strong, disappeared while escorting a spice caravan from Pentos to Myr. The Iron Brotherhood vanished after taking a contract to clear bandits from the Rhoyne approaches. Most recently, the Sunset Company - a small but well-regarded group - simply never returned from a 'routine' patrol of the border regions."
"Meaning?"
"Someone is systematically eliminating sellsword companies operating in that region. The question is whether it's a rival free city, bandits who have grown unusually organized, or something else entirely. What's certain is that the magisters are running out of reliable military options."
Kaelo set down his wine cup. "Either way, the magisters are getting desperate. They're offering double rates for contracts they used to pay standard wages for. Some are even offering triple rates for work in the Disputed Lands."
"Which brings me to the opportunity," Orbelo said, producing a small scroll from his robes. "I made a connection through a scholar I knew in Braavos, now a scribe for Magister Illyrio Mopatis, one of the wealthiest. He's built his fortune on diverse investments: cheese, silk, spices, and various other trades throughout the Free Cities. More importantly, he's known for taking calculated risks that other magisters avoid."
Jon examined the scroll - an invitation written in flowery Pentoshi script, the parchment of quality that suggested real wealth behind it. "He wants to meet?"
"Tomorrow evening. Private dinner at his manse. He claims to have work that would suit a 'small but capable company with more sense than the usual sellsword rabble.' According to my contact, Mopatis specifically requested a meeting with us after hearing about our arrival."
"Sounds too convenient," Kaelo said suspiciously. "How does he even know we exist?"
"Word travels fast in Pentos," Orbelo replied. "A new sellsword company with enough coin to pay docking fees without complaint, disciplined enough to post proper watches, and smart enough to gather intelligence before seeking contracts? That's exactly what every magister in the city has been hoping for."
"Or," Kaelo added darkly, "exactly what someone hunting sellsword companies would be looking for."
Orbelo paused, considering this. "That's... actually a disturbing possibility I hadn't fully considered."
"It's why we work together," Jon said.
Jon considered their options. They needed to establish themselves, but not at the cost of walking into an obvious trap. "What else did you learn about him?"
"Wealthy enough to be a magister, but not from one of the oldest families. Made his fortune through trade rather than inheritance. Has fingers in dozens of different enterprises - cheese, silk, information, political introductions. Known for his hospitality and his... appreciation for fine things. No immediate family, keeps his own counsel. The other magisters tolerate him because he's useful and poses no direct threat to their power."
"Or so it appears," Jon corrected. "In my experience, men who seem harmless are often the most dangerous."
"True. But he's also our best option for making the right connections quickly. The alternative is spending weeks trying to approach magisters directly, and most of them won't see unknown sellswords without proper introductions. Besides, Mopatis has never lost a sellsword company - his contracts tend to be more... creative than the standard caravan guard or border patrol work."
Jon made his decision. "We go. But carefully. I'll take you and Kaelo - enough to show respect, not enough to seem threatening. And we prepare for the possibility that this is either a trap or a test."
"What kind of preparation?" Kaelo asked.
"The kind that keeps us alive if Mopatis turns out to be less friendly than he appears."
Orbelo leaned back in his chair. "You know, six months ago I would have called this level of paranoia excessive."
"And now?" Jon asked.
"Now I'm wondering if we're being paranoid enough." Orbelo's smile was rueful.
Kaelo raised his wine cup. "To healthy paranoia, then."
"And to friends who keep us honest about our fears," Jon added, raising his own cup.
"And to the hope that tomorrow's dinner doesn't require us to test either," Orbelo finished, completing the toast.