Tolub

Captain

Captain Tolub, leader of the river pirates aboard the Red Gold, is a ruthless and charismatic figure in the village of Nulb. Known for his shaggy appearance, booming laugh, and love of brawling, Tolub rules his crew with a combination of brute force and cunning manipulation. While he claims to protect river trade from monsters and bandits, the truth is far more sinister: Tolub himself is the very threat he warns against. Under his command, the Red Gold and its crew prey upon merchant vessels along the Velverdyva River, extorting protection money from those who dare traverse his territory. He has a complex network of relationships with powerful individuals in Nulb, the Cult of the Crushing Wave, and the Temple of Elemental Evil.

Physical Description

Tolub is a bear of a man, tall and broad-shouldered, with a shaggy mane of hair and a thick beard. His skin is weathered from years on the river, and his hands are scarred from countless fights and battles. His voice is loud and rough, often punctuated by a raucous laugh. Tolub is usually seen in rugged leather armor reinforced with metal studs, but in battle, he dons a suit of enchanted studded leather and a ring of protection. His weapon of choice is a massive, enchanted greataxe, which he wields with deadly skill.

• Build: Tall, broad-shouldered, muscular 
• Features: Shaggy hair, thick beard, scarred hands
• Attire: Studded leather armor, occasionally reinforced with magical protections
• Weapon: Enchanted greataxe, wielded with impressive strength and skill

Rivermans Background

Tolub’s early life is shrouded in mystery, though some say he was once a legitimate riverman and trader before turning to piracy. He quickly rose to prominence on the river through a combination of cunning and brute strength. Eventually, Tolub established himself as the captain of the Red Gold, a notorious pirate vessel. He has since amassed a large crew of hardened criminals and enjoys an uneasy alliance with the Cult of the Crushing Wave, working closely with Belsornig, the Water Prophet. Tolub’s base of operations is the recently-occupied Riverguard Keep, an old fort he and his crew are slowly restoring to serve as a headquarters for their operations.
From legitimate roots to ruthless pirate captain, Tolub’s life has been shaped by a blend of ambition and brutality. His alliance with the Cult of the Crushing Wave and occupation of Riverguard Keep mark him as a powerful player in the region’s criminal underworld.

• Origins: Former riverman, turned pirate
• Position: Captain of the Red Gold
• Allies: Cult of the Crushing Wave, Belsornig (Water Prophet)
• Base: Riverguard Keep, serving as both a base and refuge for his crew

Motivations

Tolub’s primary motivation is power—control over the river and all commerce that flows along it. He sees himself as a ruler of the waterways, extracting tribute from merchants and brutally punishing those who refuse to pay. His alliance with the Cult of the Crushing Wave is partly pragmatic, as it allows him to access resources and information. However, Tolub is also fascinated by the power promised by the elemental cults and the growing influence of the Temple of Elemental Evil. He hopes to use these connections to expand his influence, both in Nulb and beyond.

"A good drink and a dirty deal—two things I never say no to."

Tolub’s ambitions extend beyond mere piracy; he sees himself as a force to be reckoned with, ruling over the river with an iron fist. His alliance with the elemental cults provides him with both resources and opportunities to expand his reach.

• Primary Goal: Control of river trade
• Secondary Goal: Expansion of influence through elemental cult alliances
• Approach: Fear, extortion, and strategic alliances

Relationships

Lodriss

Lodriss, the true owner of the 43: Boatman’s Tavern and Nulb Market and Tolub’s lover, plays a significant role in Tolub’s operations. While she maintains a veneer of independence, she is loyal to Tolub and helps him manage his affairs in Nulb. Lodriss often provides information and handles some of the logistical details of Tolub’s business, allowing him to focus on larger matters. Although their relationship is largely one of convenience and mutual benefit, there is genuine affection between them.

• Nature of Relationship: Lover and ally
• Role in Tolub’s Operations: Information broker and logistical support

Lady Lmag's men
Tolub has a wary respect for Lady Lmag and her followers. He views her as a valuable ally in maintaining order (or at least, organized chaos) within Nulb. However, Tolub is careful not to trust her too deeply, as he knows she has her own agendas that may conflict with his. The two share a mutual interest in keeping Nulb out of the hands of external authorities, allowing both their factions to thrive in the shadows.

• Nature of Relationship: Cautious alliance
• Shared Goals: Maintain autonomy of Nulb from external authorities

Temple of Elemental Evil and the Crushing Wave

Tolub is a high-ranking member of the Cult of the Crushing Wave, where he serves as an enforcer and ally to Belsornig, the Water Prophet. Tolub often transports goods and personnel for the temple and has been known to meet with other temple agents in Nulb. While he doesn’t fully subscribe to the cult’s fanaticism, Tolub sees the partnership as beneficial to his goals and remains a staunch supporter as long as it serves his interests.

• Position: High-ranking cultist in the Crushing Wave
• Primary Contact: Belsornig, Water Prophet
• Role: Transportation and enforcement for temple operations

Tactics and Combat

When facing adversaries, Tolub is a ruthless combatant who doesn’t hesitate to use underhanded tactics. If he recognizes the adventurers or suspects them of interfering with his operations, he may invite them to drink and gamble, using the opportunity to set up a surprise attack. Alternatively, he might attempt to divert their attention toward other cult strongholds. In combat, Tolub relies on his greataxe and will call on his crew if he believes he’s outmatched.

• Strategy with Strangers: Invite to gamble/drink, surprise attack
• Alternative Strategy: Deflection to other cult locations
• Preferred Tactics: Direct combat with greataxe, call for backup if needed

Synopsis
Tolub is both cunning and brutal in combat, willing to feign hospitality to gain the upper hand. He is capable of using both direct and indirect tactics to protect his operations.

DM-Only Section

Secret Quests and Encounters

• Meeting in Nulb: Tolub sometimes attends meetings in Nulb to negotiate trade agreements, oversee smuggling operations, or meet with other temple agents. Adventurers might intercept one of these meetings, providing an opportunity for espionage or ambush.
• Alliance with Jolliver Grimjaw: Tolub collaborates with Jolliver Grimjaw, a prominent smuggler, to transport stolen goods along the river. This alliance connects Tolub to a larger criminal network and provides valuable intelligence for the adventurers.
• Ambush Strategy: If Tolub recognizes the adventurers, he might play dumb and invite them to drink. At the right moment, he signals his crew to launch a coordinated attack. Alternatively, he might attempt to divert them to other cult targets, like the Hall of the Scarlet Moon.

Tolub's Treasure

Tolub carries several valuable items, including a ring of protection +1, an opal ring worth 2,000 gp, and studded leather armor +1. Additionally, a hidden cache aboard the Red Gold contains smuggled goods, valuables, and supplies intended for temple operations.

Key Points

• Captain of the Red Gold: Tolub is a charismatic and brutal pirate leader with ambitions to control the river trade.
• Cult Alliance: Tolub is a high-ranking member of the Crushing Wave cult and collaborates with Belsornig and other temple agents.
• Strategic Planner: Known for his cunning in battle and manipulation in social interactions, Tolub uses tactics that suit his goals.
• Secret Motivations: Tolub has complex motivations, driven by power, profit, and his desire to maintain control over the riverways.

Tolub’s Secret Actions and Tactics

Tolub’s Strategic Meetings and Activities

1. Overseeing Trade Agreements with Temple Agents

Tolub frequently arranges clandestine meetings with agents of the Temple of Elemental Evil in Nulb. It’s far easier and faster for him to meet with these representatives at a neutral location, like the Boatman’s Tavern, than to undertake the journey to the Temple itself. When negotiating these agreements, Tolub ensures that he always receives a hefty cut of the profits from smuggling goods or transporting Temple supplies. He is well-aware of the high stakes involved in Temple dealings and leverages his position to keep his crew funded and loyal.

2. Coordinating with Bandit Leaders for Slave and Supply Exchanges

Tolub often meets with local bandit leaders to arrange exchanges of slaves or supplies. These deals strengthen his influence over the criminal networks around Nulb and ensure that he has allies beyond the river. Tolub is particularly interested in acquiring strong and capable slaves, whom he can sell at a premium or train to bolster his crew. By supplying the Temple with such "resources," Tolub further ingratiates himself with its leaders, particularly those in the Earth and Water Temples, who find these contributions invaluable.

3. Planning with Lady Lmag at Easthome

Tolub occasionally meets with Lady Lmag at her estate, Easthome, to discuss regional control and mutual goals. Lady Lmag’s influence in Nulb provides Tolub with a powerful ally among the more organized elements of Nulb’s criminal underworld. Together, they coordinate efforts to keep Nulb in chaos, ensuring it remains an appealing haven for illicit activities. Their plans often revolve around strengthening Nulb as a base for piracy and smuggling, solidifying the village as a key outpost for Temple activity and a buffer against the forces of law and order from Verbobonc.

4. Meeting with Belsornig at the Boatman’s Tavern and Nulb Market

Tolub occasionally meets with Belsornig, the Water Prophet, at the Boatman’s Tavern to exchange information and solidify their shared goals. While Tolub sees himself as an independent force, he recognizes the benefits of aligning with the Crushing Wave’s operations, particularly when it comes to maintaining control over the river routes. Belsornig values Tolub’s expertise in piracy and has even considered recruiting some of his tougher crew members into the ranks of the Water Temple. Together, they discuss strategies for disrupting Verbobonc’s trade routes, amassing wealth, and establishing the Crushing Wave as the dominant faction in the region.

Tolub’s Crew and Resources

Tolub’s crew of 40 pirates is divided into three rotating groups:

• One-fourth remain with him at the Boatman’s Tavern, providing a strong presence in Nulb and ready support for any operations within the village.
• Half of his crew are typically sailing on the river, either patrolling, raiding, or transporting illicit cargo between Nulb and various hideouts.
• The remaining quarter guard his flagship, The Red Gold, maintaining its readiness for rapid departure or defense. This crew is on high alert to prevent sabotage or theft and to defend Tolub’s ship from any potential threats.
• When Tolub is unavailable, his lieutenant, Grud Squinteye, assumes command of the crew at the tavern and follows the same protocol.

Tolub’s Tactics and Responses to Adventurers

Reaction Upon Recognizing Adventurers

Tolub, a savvy and seasoned pirate, knows that adventurers often pose a threat. When he recognizes such individuals in his territory, he considers several possible responses based on his evaluation of their strength:

• Feigning Ignorance: Tolub often pretends to be a mere brawler and tavern regular, inviting the adventurers to drink and gamble with him. This casual demeanor lulls the characters into a false sense of security. If they fall for the ruse, he subtly signals his crew to launch a surprise attack, using the opportunity to rob or capture them.
• Deflecting and Deceiving: In instances where he deems the adventurers too dangerous to confront directly, Tolub feigns ignorance while subtly deflecting their attention. He directs them toward the Hall of the Scarlet Moon, spinning tales of possible answers to their quest there. Meanwhile, he discreetly dispatches a bandit to warn the Fire Prophet, who will then prepare an ambush for the adventurers.
• Immediate Assault: If Tolub is confident in his advantage—or if he’s cornered without an easy escape—he attacks the adventurers directly, calling on his crew for backup. Tolub fights ferociously, relying on his magic greataxe and leather armor reinforced with magical protection.

Escaping to the River If the fight turns against him, Tolub is quick to flee. His knowledge of the terrain around Nulb allows him to find his way to the river with ease, where he can leap into the water and swim to safety. This tactic has saved him more than once, as he is adept at navigating currents and evading pursuit. Tolub is deeply familiar with the river paths and secret inlets, making him nearly impossible to track once he escapes into the river.

Tolub’s Relationship with Key Figures

• Lodriss: Lodriss, the owner of the Boatman’s Tavern and Tolub’s mistress, is an essential ally. She helps keep his activities in Nulb under control, acting as both confidant and informant. However, Tolub knows that her loyalty is conditional; if Lodriss perceives a threat to her own position, she might turn against him. This keeps Tolub wary, ensuring he never fully trusts anyone—even his closest allies.
• Belsornig: As a high-ranking member of the Crushing Wave, Tolub has a close working relationship with Belsornig. The two share a mutual interest in disrupting Verbobonc’s trade and amassing wealth through piracy and smuggling. Belsornig respects Tolub’s tactical mind and often consults him on river-based operations, particularly when they involve attacks on merchant vessels.
• Lady Lmag: Tolub’s relationship with Lady Lmag is more strategic than personal. As a powerful figure within Nulb, Lady Lmag serves as a critical point of connection between Tolub and the Temple’s broader network. Their discussions are typically centered around mutual interests in maintaining Nulb’s chaotic environment and enhancing the power of their respective factions.
• The Hangmen: While Tolub has little direct loyalty to the Hangedmen, he respects their influence and keeps a cautious alliance. He occasionally provides river transport for their captives or loot, viewing this collaboration as a mutually beneficial arrangement that strengthens his foothold in the region.

Quest: The Drunken Sailor

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Level: Suitable for party level 3
Location: 43: Boatman’s Tavern and Nulb Market 

Overview

During a late evening in Nulb, the adventurers find themselves at the notorious Boatman’s Tavern, a favored haunt of the river pirates. It’s a rowdy night, filled with laughter, drinking songs, and the occasional brawl. Amid the noise, a heavily inebriated pirate from Captain Tolub’s crew—rumored to be a close confidant of the captain himself—staggers out of the tavern, swaying dangerously as he steps onto the pier.
The pirate trips over his own feet and tumbles over the edge of the pier into the murky marsh water below. As he struggles to keep his head above the water, his drunken cries echo through the night. The adventurers have a choice: rescue him, or leave him to his fate. This moment of decision opens up an opportunity to gain valuable information, along with potential allies in Nulb.

Encounter Description

If the adventurers decide to intervene, they’ll find the pirate flailing in the water, his clothing weighed down by his gear and booze-soaked coat. He is grateful, if a bit belligerent, and doesn’t hesitate to slur a few vague insults as they pull him to safety. Once out of the water, he collapses in a heap on the pier, coughing and spluttering, but slowly regaining his senses. This is their chance to question him about the river pirates and Captain Tolub’s dealings.

Key Information the Pirate Can Provide

After some gentle—or not-so-gentle—persuasion, the pirate begins to loosen up and share his knowledge. Here’s what he reveals:

• The Pirates' Relationship with the Temple of Elemental Evil
• He confirms that Captain Tolub and his crew have no formal alliance with the Temple of Elemental Evil. 
• The pirates are not aligned with any one faction, preferring to remain independent and sell their services to the highest bidder. However, they occasionally take jobs from temple agents for the coin.

You haul the soaked pirate up onto the pier, his soaked clothes clinging to him as he collapses in a soggy heap at your feet. He coughs and sputters, wiping muddy water from his face with a rough, calloused hand. As his breathing steadies, he glances up at you with bloodshot eyes, his voice dripping with sarcasm and a slurred edge.
“Suppose I... owe you one, eh? Not that I asked for a bloody rescue,” he grumbles, attempting to pull himself up, but slipping slightly on the wet planks. “Woulda made it out just fine, given a few more minutes—just a bit of bad luck with the pier, that’s all.”
He narrows his eyes, looking you up and down as if weighing you. “Guess you’re not from around here, huh? Too clean... too upright.” He spits a bit of marsh water and lets out a low chuckle. “You lot oughta watch yourselves, poking around Nulb like yer saints come to save the day.”
Another coughing fit doubles him over, but he straightens, rubbing his neck and nodding grudgingly. “Still... reckon I oughta thank ye. Even if you are a bunch of do-gooders. Just don’t be thinkin’ this gets you a free pass with Captain Tolub or the rest of us.”
He smirks, then gestures vaguely back at the tavern with a jerk of his thumb. “Suppose I could... answer a question or two, seein’ as I owe you. Just don’t expect me to spill all me guts. Captain wouldn’t be too happy if I did.”

The Mysterious Men in Black Cloaks

Recently, men in black cloaks, bearing the symbol of the Elder Elemental Eye, have been making frequent appearances in Nulb, especially whenever Tolub is in town. These strangers seem intent on pressuring Tolub into an arrangement, though the pirate isn’t sure what they want. However, he has seen them storm off after meetings with the captain, clearly angered by Tolub’s defiant refusal to comply.

Captain Tolub’s Frustration

The pirate mentions that Tolub grows angrier with each visit from these cloaked men. He describes Tolub’s barely restrained temper after these meetings, muttering about “not taking orders from some shadowy cult.” Tolub’s crew is fiercely loyal to their captain and equally suspicious of these outsiders meddling in their affairs.

Quest Outcome

If the adventurers show kindness to the pirate by helping him out of the water, he expresses his gratitude, albeit clumsily. As a show of thanks, he offers them a small trinket—a tarnished silver coin stamped with an unfamiliar pirate insignia—that might be useful for gaining trust or at least recognition among the river pirates.
The pirate also hints that if they’re looking to make an impression in Nulb, it would be wise to keep a low profile and stay out of Lady Lmag's way. He advises them, “Don’t stick yer neck out too far—round here, it’s liable to get cut.”
This small act of mercy could have greater repercussions down the line:

Otis’ Approval

If Otis catches wind of their kindness toward the pirate, it may influence him positively, even if he remains cautious. Otis is known to observe newcomers carefully, and this act of aid might incline him to approach the party sooner, especially if Elmo hasn’t already vouched for them. The pirate’s story of the adventurers’ actions might reach Otis and help build trust.

Future Leads and Allies

The adventurers might find that, should they ever need information or assistance related to Tolub’s crew, their name might be remembered among the pirates. This could help them secure an audience with Tolub himself, should they need to in the future.

Quest Rewards

• Small Trinket: The pirate’s silver coin with the river pirate insignia (symbolic value for establishing a reputation in Nulb).
• Potential for Otis’ Favor: Increases the chance that Otis may cautiously approach the adventurers as allies in the battle against the forces of Evil in the region.
• Insight into Temple Relations: Knowledge that the Temple of Elemental Evil is attempting to draw Tolub and his pirates into their machinations—though Tolub resists, the adventurers now know that the Temple is growing more insistent in its reach.

Additional Details

The pirate may not fully grasp the implications of his information, but his account is accurate. The Temple of Elemental Evil, through agents bearing the Elder Elemental Eye, is attempting to sway Captain Tolub into their service, either through threats or bribery. Tolub’s defiance stems from his pride and independence; he sees himself as master of the river, not some puppet of the Temple’s agenda. However, if the pressure continues, Tolub may eventually feel cornered, which could lead to more violent clashes or desperate deals.

Follow-Up Encounters

As the adventurers delve deeper into Nulb’s secrets, they may cross paths with Tolub, Lady Lmag’s agents, or the Temple’s black-cloaked cultists. Each encounter could reveal more about the mounting tensions among Nulb’s factions.
This quest serves as a stepping stone, introducing the adventurers to the shadowy dealings in Nulb and hinting at the Temple’s efforts to manipulate the region through alliances and intimidation. By aiding a pirate, the adventurers gain insight into the complex power dynamics—and perhaps, for now, a fragile ally in the form of Captain Tolub’s crew.

Quest: Tolub's Journal

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Quest Level: Suitable for party levels 3 or 4
Location: Nulb, aboard The Red Gold, Tolub's river pirate ship

Overview

Otis, the blacksmith and secret agent of Veluna, has been tasked with assessing Captain Tolub’s true allegiances. The spymaster in Veluna suspects that Tolub may be aligned with darker powers, perhaps even the Temple of Elemental Evil, but Otis has struggled to gain concrete proof. Tolub’s mistrustful nature and the constant presence of armed pirates make it impossible for Otis or his sprite allies to slip aboard the ship unseen. He turns to the adventurers, hoping they can retrieve Tolub’s journal from his private quarters on The Red Gold, which may contain the information needed to confirm or refute his loyalties.

Objective

Retrieve Tolub's personal journal from his sealed cabin aboard The Red Gold and deliver it to Otis. The journal must be taken without alerting Tolub or his crew, and Otis discourages outright violence against the pirates if possible.

Otis, the broad-shouldered blacksmith, approaches you with a wary glance over his shoulder. His voice is low, gravelly, and his eyes dart toward the door to make sure no one’s within earshot. “Got a moment?” he asks, motioning you closer to his forge, where the clinking of tools provides a comforting mask to your conversation. "I’ve got a job that requires... a delicate touch, shall we say." He gives you a long look, sizing you up to see if you’re the type to handle something beyond sword-swinging and spell-slinging.
“There’s a man here,” he continues, eyes narrowing slightly. “Captain Tolub. Runs his crew out of The Red Gold on the river. A brash sort, boisterous, always in his cups... but not half as foolish as he lets on. He’s got a journal, you see. Keeps records of his, ah, transactions, meetings, and other dealings.” Otis leans in, his voice barely above a whisper. “That journal might be exactly what I need to know where his true loyalties lie.”
He clears his throat and glances at you pointedly. “But his crew watches him like hawks. They’re as loyal as they are suspicious, and if they so much as sniff trouble, I’ll be in the pot with you. So here’s the thing—no killing. None of his crew should end up gutted or missing. That would arouse suspicions, and I can’t afford the attention.”
Otis takes a deep breath, his gaze serious and unwavering. “If you can slip aboard his ship, get that journal, and slip back off without stirring up trouble, I’ll make it worth your while. I’ve got a stash of gems hidden away—500 gold’s worth, and they’re yours if you pull this off clean.”
His eyes hold yours, steady and intent. “Can I count on you for something... discreet?”

Quest Details

Quest Hook

Otis discreetly approaches the party at his smithy, where he outlines the delicate mission. He explains that Tolub’s journal could contain records of secret meetings, transactions, or even alliances that would reveal his true intentions. However, Otis cautions that Tolub’s crew is always alert and protective of their captain. Any violence or bloodshed could arouse suspicion and jeopardize Otis’s cover as a simple blacksmith in Nulb.
Otis promises the party 500 gp worth of gems from his hidden stash beneath the anvil in his shop if they can complete the mission without killing any of Tolub’s men. The gems are a mix of modestly valuable stones, likely gathered from various covert missions he’s undertaken over the years.

Challenges

• Stealth and Disguise: The party will need to approach The Red Gold under the cover of night or use creative disguises to blend in with the riverside crowd. Pirates are used to strangers in Nulb but are likely to question anyone attempting to board Tolub’s ship uninvited.
• The Bosun and Docking Crew: Tolub’s bosun, a tough and suspicious pirate, leads the small group of men stationed on the ship at all hours. The party will need to evade or distract these pirates to gain access to Tolub’s quarters. They may need to create a diversion or use spells like Sleep or Charm Person to slip past them undetected.
• Tolub’s Sealed Cabin: Tolub’s private quarters are fortified with a heavy, locked door, and he keeps his journal well-hidden. This may require a character skilled in lockpicking or someone with access to spells like Knock. The room itself is modest but secure, with a hidden compartment under the bed or behind a loose floorboard where Tolub keeps his journal.

Enemies

• Pirates on Watch (8): Use Bandits from the Monster Manual (p.343) for stats. Each pirate provides 200 XP if defeated, though the party should avoid lethal combat if possible.
• Tolub's Bosun: Slightly tougher than the other pirates, the bosun is sharp-eyed and may take charge if alerted to intruders. Treat him as a Bandit Captain if a combat encounter occurs.

Rewards

• 500 gp in Gems: If the party successfully retrieves the journal without killing any pirates, Otis rewards them with 500 gp worth of gemstones from his hidden stash.
• Otis's Favor: Successfully completing this mission will earn the party Otis’s trust. In the future, he may be more willing to share intelligence on Nulb’s underground activities, provide minor supplies, or even accompany them on expeditions against the Temple of Elemental Evil.

Possible Outcomes

• Success Without Detection: If the party retrieves the journal without arousing suspicion, Otis is deeply impressed. He rewards them promptly and even hints that he may have other “jobs” for adventurers with their particular skills.
• Success with Alarm Raised: If the party is detected but manages to escape with the journal, Otis will still reward them, albeit with a scolding for the unnecessary attention. Tolub may become suspicious and increase his guards or take precautions in the future, potentially complicating future missions in Nulb.
• Failure or Capture: If the party is caught in the act, they may find themselves imprisoned or facing Tolub's wrath. They might be forced to bribe their way out or find an alternative means of escape. If they escape without the journal, Otis will be disappointed but may still be open to working with them if they prove useful in other ways.

Quest: The Elf at Knifepoint

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*For Characters Level 3*

Synopsis

While in the village of Nulb, the players encounter an elven scout, Jassin Valee, held at knifepoint by a group of Tolub’s pirates. The elf is an agent of Celene on a desperate mission to find Countess Trillahi, rumored to be a captive of cultists in the region. If the PCs choose to intervene, they’ll risk gaining Tolub’s ire, but a successful and non-lethal rescue could earn them a powerful ally and potential rewards from Celene.

Quest Details

Location The wharf area near abandoned buildings on the edge of Nulb.

Objective

Rescue the elven scout Jassin Valee from Tolub's pirates without killing them or alerting Tolub. Stealth, non-lethal methods, or clever diplomacy are encouraged to avoid escalating tensions with the pirates.

Encounter Setup

As the PCs make their way along the docks, they spot a group of rough-looking pirates surrounding a slender figure with pointed ears. The elf is backed against the edge of the wharf, one hand raised defensively while the pirates jeer, knives gleaming in the dim light.

Dialogue Prompt (Pirates)

"Where’s your fancy magic now, elf?" one pirate sneers, waving his blade. "You’re far from your tree-huggin' friends. Let’s see if you’re so high and mighty without 'em!"

Key NPCs

Jassin Valee (Elven Scout)

Jassin is an agent of Celene, tasked with tracking down Countess Trillahi, a noble elf rumored to be taken by cultists. He will provide information on the cult’s activities and mention that Celene will richly reward anyone who can confirm Trillahi’s safety or provide proof of her fate.

• Disposition: Distrustful but respectful to those who help him.
• Motivation: Recovering Countess Trillahi safely or, failing that, learning her fate.

Dialogue Prompt (Jassin)

“Thank you… I owe you a great debt. But this is far from over. I have been following whispers, rumors of a barge carrying prisoners—some who might be… like me. My Countess is among them. If you aid me further, Celene will not forget your valor.”

Quest Details

Background Information

Jassin reveals that Countess Trillahi of Celene, along with her consort, Sir Juffer, may have been captured by cultists. They were last seen being transported on a barge manned by green-robed figures, likely connected to a dangerous sect associated with the Temple of Elemental Evil. Jassin suspects the cultists plan to use the prisoners in a dark ritual

Optional Information

• Jassin shares that there have been sightings of men in black cloaks bearing the mark of the Elder Elemental Eye, pressuring the pirates in Nulb.
• He believes that a hideout lies further south, possibly within the Water Temple or another location tied to the Temple of Elemental Evil.

Rewards

Immediate Reward
If the PCs manage to rescue Jassin non-lethally, he will vouch for their bravery and send word to Celene regarding their deeds.
Experience Points (XP): 300 XP for resolving the encounter without violence.

Long-Term Rewards

• Elven Chain Armor (human-sized): Delivered to the party leader in 5-8 weeks.
• Unicorn Horn Ring (enchanted): Awarded to the most gallant party member, enchanted with a permanent *sympathy* effect toward unicorns (1,000 XP). If the wearer becomes evil or harms a unicorn, the ring will vanish unnoticed.
• Platinum Reward: Each party member receives 100 platinum pieces, arriving 5-8 weeks after the rescue.

Tactics for the Encounter

Pirates' Behavior

The pirates are arrogant and believe they’re untouchable in Nulb. If the PCs approach, the pirates may mock or threaten them, depending on their approach. However, they’re not interested in a fight unless provoked.

Alternative Solutions

• Stealth Approach: The PCs can attempt to stealthily dispatch or disable the pirates without killing them, allowing Jassin to escape.
• Bribery or Bluff: Clever PCs might persuade or bribe the pirates to release Jassin, perhaps by pretending to be agents of Tolub or the Temple.
• Non-Lethal Combat: If combat occurs, encourage the PCs to use non-lethal methods to subdue the pirates without killing them, as this will prevent worsening relations with Tolub.

Aftermath and Consequences

Tolub’s Reaction

• If the PCs kill the pirates, Tolub will likely retaliate, making future interactions with his crew and other pirates more hostile.
• If the PCs handle the encounter non-lethally, Tolub might remain unaware, and Jassin’s gratitude could open future opportunities for alliances or rewards.

Additional Story Hook

Next Steps with Jassin
Jassin encourages the PCs to investigate the cult further, hinting that the Temple of Elemental Evil has deeper connections to the missing Countess. He may join them briefly or provide information on safe travel routes and potential dangers.

Quick Reference Summary for the DM

• Quest Level: 3
• Objective: Rescue Jassin Valee non-lethally and gain information about the cult’s involvement with the Temple of Elemental Evil.
• Rewards: 100 platinum per party member, Elven Chain Armor, Unicorn Horn Ring with *sympathy* effect (for unicorns), 300 XP for the encounter.
• DM Tips: Keep the encounter flexible; allow the PCs to resolve the situation using stealth, diplomacy, or non-lethal combat.
• Long-Term Impact: Success in this quest can lead to alliances with Celene and reinforce Otis’s trust in the party.

"There’s two ways off this river: by my leave, or by my blade."

Captain Tolub

Leader of The River Pirates 
Medium humanoid (human), Fighter (Level 8)

• Armor Class 17 (studded leather +1, ring of protection +1)
• Hit Points 62 (8d10+15)
• Speed 30 ft.
• STR DEX CON INT WIS CHA
• 17 (+3) 15 (+2) 15 (+2) 9 (-1) 10 (+0) 17 (+3)
• Saving Throws Str +6, Dex +5, Con +5
• Skills Intimidation +6, Athletics +6
• Senses Passive Perception 10
• Languages Common
• Challenge 3 (700 XP)

Actions

Multiattack. Tolub makes two attacks with his greataxe or scimitar.

• Greataxe +1. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 11 (1d12 + 4) slashing damage.
• Scimitar. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 4) slashing damage.
• Dagger +2. Melee or Ranged Weapon Attack: +7 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 6 (1d4 + 4) piercing damage.

Equipment & Treasures

Carried: Battle axe +1, dagger +2, purse with 7 ep, 14 gp, and 10 pp; black opal ring worth 6,000 gp.

Traits

• Ruthless Leader. Tolub can issue commands to his crew as a bonus action. When he does, allies within 30 feet gain advantage on their next attack roll.
• Cunning Escape. If Tolub's hit points drop below 15, he can take the Disengage action as a bonus action and flee to a defensible position or leap into the river if near water.

Background Notes: Tolub is the ruthless captain of the Red Gold and leads a crew of river pirates operating out of Nulb. He’s a high-ranking member of the Cult of the Crushing Wave and well-informed on local affairs. He may recognize adventurers by reputation and adjust his behavior accordingly.

Pirate Crew (for either Tolub or Grud):

Name, Level, HP. armor, weapon
1st mate* 4 23 Chain + shield Longsword
2nd mate 4 21 Chain + shield Morningstar
Bosun 2 12 Chain Battleaxe
B'mate 0 7 Chain + shield Longswrd axe
B'mate 0 6 Chain Basterd Sword
2 Sailors 0 5 leather
6 Sailors 0 4 leather
4 Sailors 0 4 leather
2 Sailors 0 4 leather
4 Sailors 0 3 leather

1d6 roll Crew in Port

• 1. Both out raiding for 3 days
• 2. Tolub in port for 1 night
• 3. Tolub in port for 2 days
• 4. Grud in port for 1 day
• 5. Both crews in for 1 night*
• 6. Check again, rolling Id4

Alignment

Neutral evil

Current Location

43: Boatman’s Tavern and Nulb Market

Species

Humans of Greyhawk

Ethnicity

Oeridian Oerid

Year of Birth

544 32 Years old

Sex

male

Eyes

fierce hazel

Hair

Shaggy hair, thick beard

Height

6'3"

Quotes & Catchphrases

"You cross my river, you pay my price—simple as that."

The Crew of the Red Gold

Tolub leads a crew of 40 river pirates, though only a quarter are with him at any given time. His first mate, Grud Squinteye, often commands the rest. Tolub’s crew includes a mix of fighters, sailors, and other river-dwelling ruffians. The crew operates under a pirate charter, which dictates their duties and shares of the loot.

• Crew Composition: 40 river pirates, mix of roles
• Command Structure: Tolub as captain, Grud Squinteye as lieutenant
• Operating Guidelines: Pirate charter, determining shares and responsibilities

Meeting Captain Tolub

As you step into the dimly lit Boatman’s Tavern, the raucous laughter and clinking of mugs fade to a low murmur as the patrons notice your entrance. At the center of it all, a hulking figure with a mane of shaggy hair and a thick beard squints in your direction, his scarred hands wrapped around a tankard. This is Tolub—Captain of The Red Gold, leader of the river pirates, and unmistakably the man in charge here. His eyes, sharp and calculating, sweep over you, taking in every detail of your gear and stance.

He raises his tankard in a mock salute, his voice a rough rumble that cuts through the smoky air. "Well now," he drawls, his tone friendly but laced with curiosity, "ain't often I see fresh faces strollin' into my tavern, and lookin' so… well-armed, too." He takes a slow, deliberate sip of his drink, eyes never leaving yours. "What brings you lot to Nulb, eh? Sightseein'? Or perhaps…" he pauses, letting his gaze linger just a moment too long, "a bit of work?"
You can feel the eyes of his companions narrowing in on you, their postures shifting as they settle back to watch. Around Tolub’s table sit four of his crew—a ragged, dangerous-looking bunch. Each one bristles with rough-hewn confidence and the scars of a hard life on the river. The largest of them, a grizzled brute with a crooked grin, chuckles low under his breath, nudging the wiry sailor next to him with an elbow. “Fresh meat, eh?” he mutters, loud enough for you to hear, and his grin widens as he sizes you up like a butcher eyeing livestock.
Another pirate, a slender, sharp-eyed woman with a mess of wild hair, lazily runs a finger along the edge of her dagger. She doesn’t take her eyes off you, and there’s a gleam of something dangerous in her gaze—a silent dare, as if she’s measuring how much fight you’ve got in you.
Tolub raises his tankard again, casting a sidelong glance at his first mate, a scarred, one-eyed brute who leans in close. “You reckon they’re lookin’ for work or trouble, Cap’n?” he drawls, his voice a rough whisper, though he doesn’t seem too concerned about keeping it private.
You sense a mixture of interest and suspicion in his eyes, as though he's already weighing your purpose. He leans forward, voice dropping to a near whisper, though you’re certain everyone nearby is listening. "See, folk like you don’t wander into this town without a reason. Not unless you’re lost… or lookin’ for somethin' specific." He flashes a grin, his teeth glinting in the low light, but his eyes stay cold. "So, which is it? Friends of Lady Lmag, perhaps? Or… friends of the law?"
Tolub’s grin fades just slightly, and he watches you with a measured look. "Y’see, Nulb’s got all sorts," he continues, tapping his fingers rhythmically on his tankard, "traders, rivermen, and folks who don’t take kindly to strangers askin' too many questions." He gestures around the room, where eyes flicker away from you—either out of caution or quiet threat. "Lucky for you, I’m a curious sort, and I like knowin’ who’s who around here. So… how 'bout we skip the pleasantries? You tell old Tolub who you are, and maybe, just maybe, I’ll tell you what you’re gettin’ yourself into."

Around him, his crew watches you closely, fingers tapping on tankards or resting on weapons, muscles tense and ready. The atmosphere thickens with the weight of their suspicion, each one daring you to give the wrong answer. He leans back, crossing his arms over his chest, and tilts his head, waiting. The weight of his gaze feels like a test.