Tricky McCallister

Captain (a.k.a. Captain Tricky)

Tricky McCallister, often referred to simply as "Captain Tricky," is an eccentric and enigmatic figure among the pirates and merchants of Nulb. Known for his cunning and flair for deception, he commands the Tramp Queen, a merchant ship with a reputation for questionable cargo and questionable dealings. While ostensibly a neutral opportunist, Tricky’s alliances and contracts reveal a deep connection to the growing influence of the Temple of Elemental Evil, making him a crucial character in the shadowy machinations of Nulb's underworld.

Physical Description

Tricky McCallister stands at 5'11" with sleek, shoulder-length brown hair and piercing dark brown eyes that seem to scrutinize everything and everyone around him. His attire is flashy and ostentatious, favoring embroidered vests, long leather boots, and a wide-brimmed hat adorned with an oversized feather. His weathered face betrays years of maritime experience, though his refined mannerisms often disguise his true nature as a hardened opportunist.

Pirates Charm

Tricky’s outward appearance strikes a balance between charm and intimidation. Though he lacks the physical prowess of many of his crew, his commanding presence and sharp tongue make him a figure to be reckoned with in Nulb.

Personality

Tricky’s demeanor is as unpredictable as the tides. He exudes charm and sophistication but has an undercurrent of ruthless pragmatism. He is known for his clever wordplay, quick wit, and ability to twist situations to his advantage. Tricky is fiercely loyal to his ship and crew, but his ultimate allegiance lies with profit and survival. Tricky’s personality combines charisma and calculated deceit. His ability to manipulate and charm his way through conflicts ensures his survival in Nulb’s dangerous waters.

• Traits: Cunning, opportunistic, eccentric
• Flaws: Arrogant, prone to overconfidence in his bluffing abilities
• Strengths: Master manipulator, skilled negotiator, clever strategist

Background

Tricky McCallister was born in 533 CY in a port city along the Wild Coast. Though he started as a simple deckhand, his knack for persuasion and ambition quickly elevated him to the rank of captain. The Tramp Queen, once a modest merchant vessel, became Tricky’s domain, and over the years, he transformed it into one of the most feared and respected ships on the Nyr Dyv.
Tricky’s operations expanded dramatically after aligning himself with the Temple of Elemental Evil. Recognizing the profit potential in supplying the Temple’s factions, he established lucrative trade routes, ensuring a steady flow of goods into Nulb.

Key Events in Tricky’s History

Tricky’s life is a tale of ambition and survival. From humble beginnings, he has navigated the dangerous world of piracy and forged powerful alliances that ensure his continued success.

• Rise to Captain: Earned his ship through a combination of cunning and betrayal.
• Temple Connections: Became a key supplier for the Temple of Elemental Evil.
• Alliance with Tolub: Strengthened his position in Nulb by forming a partnership with Captain Tolub and other pirate factions.

Motivation

Tricky’s primary motivation is wealth and influence. He thrives on the chaos and danger of his lifestyle and sees the Temple’s rise as an unprecedented opportunity to secure his place in the annals of maritime power.

Goals

Tricky’s motivations are firmly rooted in greed and ambition. However, his ability to balance pragmatism with charm makes him more than a simple villain—he’s a master opportunist.

• Expand his contracts to include all factions of the Temple.
• Establish dominance over Nulb’s trade and smuggling routes.
• Secure the loyalty of his crew and maintain control of the Tramp Queen.

"There’s only two things I care about: my ship and my profits. Everything else is just cargo."

Relationships

Tricky’s relationships are carefully managed to maximize profit and minimize risk. He balances alliances with the Temple, Lady Lmag, and Tolub, ensuring his survival in Nulb’s volatile power dynamics.

• Lady Lmag: Tricky maintains a professional yet cautious relationship with Lady Lmag. While he respects her authority in Nulb, he is wary of her unpredictable nature and her alignment with the Temple.
• Lady Lmag's men: Tricky often employs Lady Lmag’s Men to ensure safe passage of his cargo from the docks to the Temple supply lines. He views them as useful tools but does not fully trust them.
• Tolub and The River Pirates: As a lieutenant to Captain Tolub, Tricky’s relationship with Tolub is one of mutual respect. He recognizes Tolub’s strength and leadership but harbors ambitions of surpassing him in influence.
• Leaders of the Temple of Elemental Evil: Tricky has established contracts with the Greater Temple, Earth Temple, and Water Temple. His dealings with the Fire and Air Temples are less secure, though he actively seeks to expand his influence.

"Tolub’s got the muscle, Grud’s got the brawn, but me? I’ve got the brains, and that’s what keeps us afloat."

Economy of Nulb and the Temple Connection

Tricky’s operations are a cornerstone of Nulb’s black-market economy. By supplying the Temple of Elemental Evil with essential goods, he has created a network of trade and smuggling that ties directly into Nulb’s economic lifeblood.

Goods Supplied

Tricky’s smuggling operations are integral to Nulb’s economy. His ability to supply the Temple has made him a central figure in the village’s shadowy trade networks.

• Weapons and armor
• Ale, wine, and liquor
• Spices, cloth, and oil

DM Only Section

Show spoiler

Tricky’s Bluff

Tricky McCallister is, in truth, a 0-level NPC. His charisma, cunning, and reputation for danger mask this reality, ensuring that most who cross him believe him to be a powerful and deadly foe. This deception is one of his greatest strengths, allowing him to navigate the dangerous waters of Nulb’s underworld.

"The Temple pays well, and gold has no conscience."

Temple Alliances

Tricky’s contracts with the Temple factions are his primary source of income. These arrangements are as follows:

• Greater Temple: Supplies sent via wagons to the Hunting Cabin and Temple tunnels.
• Water Temple: Cargo delivered to Tolub for transport to the river cave.
• Earth Temple: Supplies sent to the Hunting Cabin and Temple tunnels.
• Fire and Air Temples: Potential future contracts, pending negotiations.

Detailed Supply Logistics of the Tramp Queen

Tricky McCallister's role as the principal supplier to the Temple of Elemental Evil is an intricate web of logistics, alliances, and deception. His ship, the Tramp Queen, is vital for keeping the Temple's various factions well-stocked with goods that are otherwise difficult to acquire in the region. Below are the extended details on the cargo flow and how each faction benefits from his operations.

General Cargo Unloading and Distribution

When the Tramp Queen arrives in Nulb, the ship docks at a secluded, shadowy berth along the riverbank. This area is frequently patrolled by Lady Lmag’s Men, ensuring the safety of Tricky’s cargo and discouraging prying eyes. Upon arrival:

• Cargo is unloaded under heavy guard, with both Lady Lmag’s men and Tolub’s River Pirates ensuring that no opportunistic thieves interfere.
• Goods are then stored temporarily in the Boatman’s Tavern or secret warehouses nearby, both of which serve as staging areas before distribution. These locations are well-known to locals but protected by the fearsome reputation of their proprietors and enforcers.
• Tricky’s operations rely heavily on coded manifests. Each delivery is disguised as mundane trade, but only Tricky, his trusted crew, and key Temple agents can decode the actual content and intended destinations.

Greater Temple

Primary Recipients: Feldrin, Commander of the Temple Guard, and his bandits.

• Route Details: From the docks, cargo intended for the Greater Temple is loaded onto wagons and travels south along the High Road. Approximately 10 miles outside Nulb, a concealed side trail veers into the Gnarley Forest.
• Hunting Cabin Staging Area: This rustic outpost serves as a critical waypoint where goods are offloaded and stored in a secret cellar. Bandits allied with the Temple oversee the transfer and ensure no one tracks the shipments further.
• From the cabin, the cargo enters the hidden supply tunnel that connects directly to the Temple of Elemental Evil’s subterranean levels. This network is heavily trapped and guarded by both mundane and magical means, ensuring the safety of the supply chain.

Notes for Encounters:
Adventurers may stumble upon this route by encountering Feldrin’s guards patrolling the High Road or lurking near the trailhead. Intercepting one of these shipments could alert the Temple, leading to increased patrols and countermeasures.

Water Temple

Primary Contact: Belsornig, Prophet of Water.

• Role of Tolub: Tricky relies entirely on Tolub’s pirate network to handle deliveries to the Water Temple. Once unloaded in Nulb, cargo destined for the Water Temple is transferred onto smaller riverboats, helmed by Tolub or his trusted lieutenants, including Grud Squinteye.
• Hidden River Cave: The final destination is a concealed cave along the Imeryds Run, upstream from Nulb. This cave connects to the Water Temple via a network of subterranean waterways. These passages are monitored by aquatic creatures under Belsornig’s command, as well as several elite Water Temple guards.

Notes for Encounters:
The river cave is perilous, with traps designed to destroy any boat that isn’t marked with a specific sigil provided by Belsornig. This sigil is magically branded onto the hulls of Tolub’s vessels.

Earth Temple

Primary Contact: Romag, Prophet of Earth.

• Route Details: Identical to the Greater Temple, cargo for the Earth Temple also travels from Nulb’s docks to the Hunting Cabin. However, Romag insists on maintaining his own loyal guards to oversee the transfer at the cabin.
• Romag’s paranoia leads him to frequently inspect shipments personally, often clashing with Feldrin over the quality of goods received.

Notes for Encounters:
Adventurers may exploit the animosity between Romag and Feldrin to create divisions within the Temple factions. Romag’s distrust makes him more likely to negotiate with outsiders, provided they can offer information or goods of value.

Fire Temple

Primary Contact: Alrrem, Prophet of Fire (potential client).

• Tricky has yet to secure a contract with the Fire Temple, but he has sent emissaries offering deals similar to those provided to the Greater Temple. Alrrem remains cautious, unwilling to fully trust a merchant so deeply tied to the Water Temple.
• If the deal is struck, cargo for the Fire Temple would follow the same route as the Greater Temple, with goods staged at the Hunting Cabin before entering the Temple via the supply tunnel.

Notes for Encounters:
Should adventurers disrupt Tricky’s negotiations with the Fire Temple, Alrrem may retaliate against Nulb, jeopardizing Tricky’s operations and causing chaos among the Temple’s factions.

Air Temple

Primary Contact: Kelno, Prophet of Air (potential client).

• Like Alrrem, Kelno has yet to commit to working with Tricky. The Air Prophet sees Tricky as a mere opportunist and has been reluctant to entrust him with sensitive logistics.
• If an agreement is reached, Tricky plans to deliver goods via the same route as the Greater Temple. However, Kelno has hinted at needing specialized cargo, including enchanted items and rare spell components, which Tricky is currently unable to source reliably.

Notes for Encounters:
Kelno’s indecision creates an opportunity for adventurers to sabotage Tricky’s attempts to secure a deal with the Air Temple. Conversely, helping Tricky acquire the rare goods Kelno seeks could lead to future rewards—or complications.

Special Notes on Tricky’s Role in Temple Politics

• Influence: Tricky’s ability to navigate the tensions between the Temple factions makes him an indispensable ally. He uses his silver tongue and wealth to keep all sides placated, though this balancing act is precarious at best.
• Profit Motive: While Tricky is loyal to no one but himself, his business dealings directly support the Temple’s rise to power. If his supply chain is disrupted, it could severely weaken the Temple’s ability to operate effectively.
• Vulnerability: Despite his reputation as a fearsome pirate, Tricky is a 0-level human relying on cunning rather than combat prowess. Exposing this fact could shatter his authority and lead to his downfall.

Encounters with Tricky:

Adventurers seeking to weaken the Temple could target Tricky’s supply lines, sow discord among the factions, or blackmail Tricky into providing inside information. However, Tricky’s knack for deception makes him a slippery foe, and he will do whatever it takes to protect his lucrative enterprise.

Cargo and Treasure

Show spoiler

The Tramp Queen’s cargo hold often contains valuable goods, including:

• Weapons and armor (value: 10,000 gp)
• Fine liquors and spices (value: 5,000 gp)
• Miscellaneous luxury items (value: 3,000 gp)

"They call me ‘Tricky’ for a reason—cross me, and you’ll find out why.

Captain Tricky McCallister

Medium humanoid (human), Chaotic Neutral

• Armor Class 15 (studded leather)
• Hit Points 4 (0-level human, with heroic abilities)
• Speed 30 ft.
• STR | DEX | CON | INT | WIS | CHA
• 10 (+0) | 16 (+3) | 12 (+1) | 14 (+2) | 10 (+0) | 18 (+4)
• Saving Throws Dex +5, Cha +6
• Skills Deception +8, Insight +4, Persuasion +8, Sleight of Hand +5
• Tools Proficient in Navigation Tools, Vehicles (Water)
• Senses Passive Perception 10
• Languages Common, Elven, Goblin
• Challenge 1 (200 XP)

Features

• Masterful Bluff (Recharge 5-6): Tricky’s greatest strength is his ability to appear far more dangerous than he is. As a bonus action, Tricky can force one creature within 30 feet that can see or hear him to make a DC 16 Wisdom saving throw. On a failure, the creature is frightened for 1 minute. The target can repeat the saving throw at the end of each of its turns.
• Evasive Captain: When Tricky is hit by an attack, he can use his reaction to impose disadvantage on the attack roll.
• Silver-Tongued: Tricky has advantage on Charisma (Deception) and Charisma (Persuasion) checks when interacting with merchants, criminals, or those unfamiliar with his true abilities.

Actions

• Dagger. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 5 (1d4) piercing damage.
• Throwing Knife. Ranged Weapon Attack: +5 to hit, range 20/60 ft., one target. Hit: 5 (1d4) piercing damage.
• Taunt (Recharge 5-6). Tricky can insult a creature within 30 feet that can hear him, distracting it. The creature must succeed on a DC 16 Charisma saving throw or have disadvantage on attack rolls until the end of its next turn.

Equipment

• Studded Leather Armor
• Two finely balanced daggers (one jeweled, worth 200 gp each)
• Navigator’s tools and maps
• 50 gp in a hidden pouch
• A signet ring (25 gp, bearing his personal insignia of a crossed dagger and quill)
• A journal detailing trade contracts with the Temple of Elemental Evil and pirate factions

Pirate Crew of the Tramp Queen

Tricky’s crew is a mix of experienced sailors and opportunistic mercenaries, each loyal to their captain due to his charismatic leadership and knack for profit.

• First Mate: Level 4 Fighter, Chainmail, Shield, Longsword
• Bosun: Level 2 Fighter, Chainmail, Battleaxe
• Boatswain’s Mates: Two Level 1 Fighters, Chainmail, Longsword/Bastard Sword
• Sailors (14): Level 1 Fighters, Leather Armor

Alignment

Chaotic Neutral

Current Location

Nulb

Species

Humans of Greyhawk

Ethnicity

Oeridian Oerid

Year of Birth

533 43 Years old

Sex

male

Eyes

dark brown

Hair

long sleek brown

Height

5'11"

Aligned Organization

The River Pirates

Tramp Queen by 3orcs

"The Tramp Queen may look rough, but she’s never let me down. Wish I could say the same for people."