Grace O’malley

Medium humanoid (human), neutral fighter (brute) 11/rogue (thief) 5

Armor Class 17 (studded leather, fighting style)
Hit Points 115 (11d10+5d8+32)
Speed 40 ft.

STR	DEX	CON	INT	WIS	CHA
14 (+2)	18 (+4)	14 (+2)	14 (+2)	12 (+1)	14 (+2)

Saving Throws Str +7, Con +7
Skills Athletics +7, History +7, Insight +11, Perception +6, Persuasion +12; disguise kit +7, forgery kit +7, navigator’s tools +7, thieves tools +9, vehicle (water) +14
Senses passive Perception 16
Languages English, Gaelic, Latin, Thieves’ Cant
Challenge 10 (5,900 XP)

Special Traits

• Action Surge (1/short Rest). On her turn, Grace can take an additional action on top of her regular action and a possible bonus action.
• Brutal Toughness. Grace gains a +1d6 bonus to saving throws and death saves (treating final results of 20 or higher on a death saving throw as a natural 20).
• Cunning Action (1/turn). Grace can use a bonus action to take the Dash, Disengage, Hide or Use Object action, Dexterity (Sleight of Hand) check, or to use thieves’ tools to disarm a trap or open a lock.
• Fast Learner. After Grace has heard a creature speak for 1 minute or longer, she can mimic its manner of speaking as long as she knows the same language as the creature (allowing her to seem like she is local to a given region).
• Indomitable (1/long Rest). Grace can reroll a saving throw that she fails but must use the new roll.
• Second-Story Work. Climbing does not cost Grace extra movement. When she makes a running jump, the distance she covers increases by 4 feet.
• Second Wind (1/short Rest). On her turn, Grace can use a bonus action to regain 1d10+11 hit points.
• Sneak Attack (1/turn). Grace deals an extra 10 (3d6) damage when she hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Grace that isn’t incapacitated and Grace doesn’t have disadvantage on the attack roll.
• Tactician. Grace is able to use the Help action to aid an ally attacking a creature as long as the target of the attack is able to see and hear Grace and is within 30 feet of her.
• Diplomatic. Grace can make a Charisma (Persuasion) check contested by the Wisdom (Insight) check of a creature that can understand what she says during 1 minute of talking. On a success, as long as Grace remains within 60 feet of it (and for 1 minute afterward) the target is charmed by her. Grace automatically fails on the check if she or her companions are fighting the target.
• Mobility. Grace can Dash through difficult terrain without requiring additional movement. Whenever she makes an attack against a creature, she doesn’t provoke opportunity attacks from that creature until the end of her turn.

Actions

• Multiattack. Grace attacks three times when she takes the Attack action. When she uses a bonus action to engage in two-weapon fighting using a dagger, she adds her Dexterity modifier to the damage of her fourth attack.
• Cutlass. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 11 (1d6+1d6+4) slashing damage.
• Dagger (4). Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or thrown 20/60 ft., one target. Hit: 10 (1d4+1d6+4) piercing damage.
• Pistol (2). Ranged Weapon Attack: +9 to hit, range 30/90 ft., one target. Hit: 13 (1d10+1d6+4) piercing damage.
• Musket. Ranged Weapon Attack: +9 to hit, range 40/120 ft., one target. Hit: 14 (1d12+1d6+4) piercing damage.

Reactions

• Uncanny Dodge. When an attacker Grace can see hits her with an attack, she can use her reaction to halve the attack’s damage against her.

About

The cunning pirate Grace O’Malley championed the seas around Ireland and even stood up directly to Queen Elizabeth I, taking word and sword to power whenever the need called for it.

Born in 1530 to Eoghan and Maeve O’Malley, Grace was something of a favorite and she got away with a lot. The O’Malleys were one of the relatively few seafaring clans, their lands protected on the coasts by a row of castles. She received a formal education, spent plenty of time on the water, and then married Donald O’Flaherty in 1546 and had 3 kids with him: Owen, Maeve, and Murrough.

Grace is able to acquire passage on a sailing ship for her and her allies free of charge. She has no control over the ship’s route, departure, or return, and although no coin is required she and her companions do have to help crew the vessel.

Unfortunately Donald died only a few years later, killed while hunting. A short time afterward she took a shipwrecked sailor as her lover who was also killed by warriors from a rival clan. O’Malley tracked his murderers down to Doona Castle in Blacksod Bay and slew them, earning the nickname the Dark Lady of Doona.

O’Malley married again, this time to ‘Iron Richard’ Bourke, so named because of his ironworks. Over the next three decades she continued enacting vengeance upon her enemies, acquired a reputation for defeating men in battle, capturing ships, and taking castles, and personally led her