D&D 5E Mythological Figures: Grace O'Malley

This cunning pirate championed the seas around Ireland and even stood up directly to (in the same room as and in front of) Queen Elizabeth I, taking word (and sword) to power whenever the need called for it: Grace O’Malley!

Grace O'Malley BANNER 5e.jpg

Born in 1530 to Eoghan and Maeve Uí Mháille (O'Malley), Grace was something of a favorite and she got away with a lot (whether you’re talking about her youth or her older years). The Uí Mháille were one of the relatively few seafaring clans, their lands of then over 300 years (now the barony of Murrisk, or at least most of it) protected on the coasts by a row of castles. She received a formal education, spent plenty of time on the water, and then marries Dónal an Chogaidh Ó Flaithbheartaigh (Donald O'Flaherty) in 1546 and has 3 kids with him: Eoghan (Owen), Méadhbh (Maeve), and Murchadh (Murrough). Unfortunately Dónal dies only a few years later, killed while hunting in 1565. A short time afterward she takes up a shipwrecked sailor as her lover and he’s also killed by warriors from a rival clan, but this time she doesn’t just pack up her things and return home—instead she tracks his murderers down to Doona Castle in Blacksod Bay and slays them, earning the nickname the Dark Lady of Doona.

Then 1567 rolls around and she marries again, this time to Risdeárd an Iarainn (‘Iron Richard’) Bourke (so named because of his ironworks). Over the next three odd decades she continues enacting vengeance upon her enemies, acquires a proper reputation (for defeating men in battle, capturing ships, and taking castles), and personally leads her armies in battle during 3 separate rebellions against British governors. The English governor of Connacht, Sir Richard Bingham, eventually has enough of this and in the spring of 1592 her eldest son is killed, youngest son is kidnapped, and her lands are taken from her. At this point Grace is a sixty-two year old so rather than fight back with blades, she arranges to meet with Queen Elizabeth I. Being the badass she is Grace sneaks a dagger into the royal court and refuses to bow (both offenses carrying the death penalty), and declines the title of Countess—sticking by the explanation that they are equals. In the end she gets her offspring released, Sir Richard Bingham leaves Ireland, and Grace stops supporting insurgencies. But only for a while. Eventually the governor returns to Connacht and O’Malley supports Ireland in the 9 Years War against England, finally dying at the (incredible at the time) age of 72 years.

Fun fact: During a castle fight she made fun of her son, telling him, "Are you trying to hide in my arse, the place that you came out of?"
Double fun fact: Grace was literally put onto the map by the Queen of England. Who can say that?!?

o'malley isle.JPG

Design Notes: I didn’t come across much about how Grace O’Malley was a badass, and mostly just a lot of material about her being a badass so we’re leaning into “tough as nails pirate queen” with her build. Not a crack shot like Anne Bonny or a fleet commander of countless ships like Ching Shih, but a lady who can throw down with pretty much anybody and hold her own whether on the deck of a ship or in the court. As for the numbers—she came in at 10.1 via the DMG and 10.2 on the Blog of Holding. Right then, I’m off to run a game with some pirate queens now. :D

Grace O’Malley
Medium humanoid (human), neutral fighter (brutal) 11/rogue (thief) 5
Armor Class 17 (studded leather, defense fighting style)
Hit Points 115 (11d10+5d8+32)
Speed 40 ft.
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)

Background: Nautical. 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.

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 take 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.

Feat: 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.

Feat: 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.

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.

Extra Attack. 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 can add 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.

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.
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Mike Myler

Mike Myler

Mike Myler

Have you been to LevelUp5E.com yet?
Yay, I've been waiting for her! Great job. I like the fact that she's high-INT.
Aye if there's anything that's certain about her personality and modus operandi, it's that she was very cunning.

I love seeing ideas drawn from Irish legend and lore. Thanks.
There are a few others if you sift around in the article category on the top right of the page!

I read about her fairly recently looking up and validating that the women pirates thing actually happened if I recall.
Yup! There were a bunch of lady pirates. We got 3 here just in this series! :D

Mike Myler

Have you been to LevelUp5E.com yet?
3pp is pretty extensive for 5e I think it was a LazyLord variety of Noble from ToC or some such that my son was playing there for a while. ( kind of ironic i was one of at least two who paralel came up with LazyLord for 4e I called mine a Prince(ss) Build )
The 'Royal Mystic' archetype?

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