Grud Squinteye

Lieutenant (a.k.a. "Ironjaw)

Grud is a hulking Oeridian with a brutish visage that bears the wear of a hard life. His most distinctive feature is the gleaming squint, a reminder of the brawl that both nearly killed him and secured his place aboard The Iron Dagger. His broad shoulders and heavily scarred arms tell a story of countless battles, and his piercing yellow eyes betray a calculating intelligence.

"The river gives, but it takes twice as much—ask anyone who’s crossed me."

River Background

Grud was born in the slums of Safeton, a rough and lawless city on The Wild Coast known for its pirates, mercenaries, and cutthroats. Growing up amidst filth and crime, he quickly learned to fight, steal, and intimidate to survive. By the time he was a teenager, Grud had carved out a name for himself in Safeton’s Dock Quarter as a ruthless enforcer—a "fixer" for any problem that required muscle, cunning, or cruelty.
His life changed during a dockside brawl that spiraled into chaos. Captain Tolub, visiting Safeton for supplies and recruits, was ambushed by rival thugs. Grud, seizing the opportunity, stepped in and saved Tolub by taking down three attackers. In the fray, he suffered a brutal blow that shattered his lower jaw. Tolub, impressed by Grud's ferocity, saw his potential and brought him aboard The Iron Dagger.
Grud’s injury led to the squint of his visage both as a badge of pride and as a tool of intimidation. His rise through the ranks of the crew was swift, fueled by a combination of loyalty, ambition, and a taste for violence. The ship’s piratical routes took him from Wooly Bay, up the Selintan River to the Nyr Dyv, and along the Velverdyva River, where they plundered merchant vessels and smuggled goods. It was in the Imeryd’s Run near Nulb that Grud and Tolub found a lucrative base of operations, cementing their status as feared pirates.

"Nulb’s a cesspit, but it’s our cesspit, and I’ll gut anyone who says otherwise."

Personality

Grud is pragmatic and cold-blooded, though he harbors a dark sense of humor. He enjoys the chaos of piracy, seeing it as both a thrill and a means to amass wealth and power. While fiercely loyal to Captain Tolub, Grud views leadership with ambition, biding his time to one day captain The Iron Dagger.
Grud's squint is symbolic of his resilience, and he often uses it to intimidate others, glaring down on objects to display his strength. His disdain for weakness extends even to his crew, and he has little patience for incompetence or hesitation.

"I’ve chewed through steel with this jaw; you’re just another chew toy."

Motivation

Grud seeks wealth and renown, but his ultimate goal is to surpass Captain Tolub and take command of The Iron Dagger. He relishes the freedom piracy offers, but he also enjoys the respect and fear it instills in others. Though he distrusts the Temple of Elemental Evil, Grud recognizes its usefulness as a source of power and protection for Nulb’s operations.

"Cross me, and the river'll carry what's left of ye downstream."

Relationships and Alliances

• Captain Tolub: Grud owes his life and his place on The Iron Dagger to Tolub, but their relationship is strained by Grud’s ambition. He respects Tolub’s leadership but believes he could do better. He is aware of his place in Tolub’s hierarchy and does his best to stay in line, though he sometimes tests boundaries. Tolub trusts Grud with sensitive missions that require a degree of cunning and discretion, recognizing that Grud’s strengths lie in his ability to manage shady dealings and clandestine operations.
• Lodriss: Grud shares a cordial, if somewhat distant, relationship with Lodriss, the owner of the Boatman’s Tavern and Nulb Market and Tolub’s mistress. He’s careful not to overstep his boundaries with her, as he knows that Tolub’s relationship with her is politically valuable. Lodriss occasionally hints at lucrative smuggling opportunities to Grud, and he respects her knowledge of Nulb’s black market scene.
• Iron Talons: The Men of the Baroness: Grud sees Lady Nysera Krivaltis as a necessary ally in maintaining Nulb’s status as a pirate haven but dislikes her refined demeanor. He frequently undermines her authority to assert his own dominance.
• Temple of Elemental Evil: Grud is aware of Tolub’s tenuous alliances with agents of the Temple. Although he has a deep-rooted mistrust of the cultists, he keeps his opinions quiet, recognizing that there’s profit to be made. Occasionally, Grud’s missions for Tolub involve transporting goods or messages for cult members, though he makes it a point to never let them aboard the Iron Dagger unless absolutely necessary. Grud suspects the cultists have dangerous ambitions, and he would rather not be entangled in their schemes unless there’s considerable reward.
• The Hangmen: Grud has had a few dealings with the Hangmen, Nulb’s notorious bandit group. These exchanges are usually mutually beneficial, often involving the exchange of stolen goods or providing transportation for raiding parties. While Grud finds them unreliable and reckless, he values their skills in gathering intelligence on the various caravans that pass through Nulb. If Lady Nystera’s Men are too high-profile for a job, Grud knows the Hanged Men can be counted on for more aggressive tasks.

"The Old Duck don’t leave witnesses, just empty pockets and fading ripples."

DM-Only Information

Secret Ambitions

Despite his loyalty to Tolub, Grud harbors his own ambitions. He sees himself as a natural leader and often contemplates seizing more influence on the river. For now, he is content with his position, but he keeps an eye open for opportunities to expand his operations. Should Tolub’s leadership weaken, Grud might be one of the first to challenge him.

Potential Plot Hooks

• Secret Mission from Tolub: Tolub might task the PCs with assisting Grud in a smuggling operation for the Temple. Grud, however, is wary of the Temple’s motives and will try to subtly gather information from the PCs about their own stance on the cult, sensing they may have their own hidden agendas.
• Undermining Lady Nystera’s Men: Grud distrusts Lady Nystera’s agents in Nulb and would pay handsomely for information that could weaken her control over the town. He might offer the PCs a reward to sabotage one of Lady Nystera’s operations or to spy on her activities.
• Rivalries with the Hanged Men: The Hanged Men have been growing bolder, and Grud sees them as a threat to his smuggling routes. He might request the PCs “send a message” to the Hanged Men, leaving evidence that implicates a rival captain in Nulb, thereby keeping his own hands clean.
• Tolub’s Journal: Grud is aware of Tolub’s dealings with the Temple and keeps his own written records of Tolub’s comings and goings in his personal journal, hidden aboard the Iron Dagger. This journal may contain clues about Tolub’s dealings with the Temple, rival pirate captains, and other local power players in Nulb. The journal could be a valuable resource for the PCs, but Grud guards it zealously, and retrieving it without his knowledge would be a difficult task.

Grud Squinteye’s mixture of ambition, cunning, and practicality makes him an influential figure in Nulb's underworld and a valuable ally—or dangerous foe—for any adventurers brave enough to delve into the dark, treacherous waters of the Velverdyva River.

"Ye best be careful where ye tread, or ye'll find the Iron Dagger's tip buried deep!"

Grud Squinteye, Pirate Lieutenant

(Pirate, half-orc, Level 6 Fighter)

• Medium humanoid (half-orc)
• Armor Class 16 (chain mail +1)
• Hit Points 59 (6d10+18)
• Speed 30 ft.
• STR DEX CON INT WIS CHA
• 15 (+2) 12 (+1) 17 (+3) 10 (+0) 10 (+0) 14 (+2)
• Saving Throws Strength +5, Constitution +6
• Skills Intimidation +5, Athletics +5
• Senses Passive Perception 10
• Languages Common, Pirate Cant
• Challenge 4 (504 XP)

Actions

• Multiattack. Varg makes two melee attacks.
• Dagger +1. Melee or Ranged Weapon Attack: +6 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 6 (1d4+4) piercing damage.
• Shortsword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 6 (1d6+2) piercing damage.
• Flail. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 8 (1d8+4) bludgeoning damage.

Equipment

• Dagger +1, shortsword, flail
• Jeweled belt (worth 7,300 gp), earring (worth 600 gp)
• Purse with 2-12 each of copper, silver, electrum, and gold pieces

Personality

Grud is both feared and respected by the crew. His iron jaw is a symbol of his unyielding toughness, and his willingness to punish disloyalty ensures their obedience.
Notes: Grud commands his own pirate ship, The Old Duck, and is known for his sharp wit and brutal tactics.

Pirate Crew:

• 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

Alignment

Neutral Evil

Current Location

4: Boatman’s Tavern and Nulb Market

Species

Humans of Greyhawk

Ethnicity

Oeridian Oerid

Year of Birth

541 35 Years old

Current Residence

The Iron Dagger

Sex

male

Eyes

dark hazel squint; he constantly narrows his left eye

Hair

hort, scruffy beard peppered with gray

Height

6'3"

Quotes & Catchphrases

"On The Iron Dagger, there’s two rules: follow orders or feed the river."

Aligned Organization

The River Pirates

Other Affiliations

• The Iron Dagger

Ruled Locations

• 29. Grud’s Cottage