Since the rise of Bretony, “Pirate” has become a catch-all term for every thief, criminal, smuggler, racketeer, and cutthroat that the powers-that-be would like to clap in irons and hang from the highest tree. And yet the more the Empire and its counterparts crack down, the more demand there is for those skilled in conducting illicit business on or adjacent to the sea. A thriving black market economy has arisen throughout the Endless Isles, and while the brand “pirate” can mean a one-way trip to the gallows, it is also rapidly becoming the surest way for someone born without wealth or title to make their fortune.

Hit Die: 1d8
Primary Attribute:
Saving Throw Proficiencies: Dexterity, Intelligence
Weapon and Armor Proficiencies: Simple weapons, hand crossbows, longswords, rapiers, shortswords, light armor


Specialist (Level 1): Choose two of your skill proficiencies. Your proficiency bonus is doubled for any checks made with those skills.

Vital Strike (Level 1): Once per turn while wielding a ranged or finesse weapon you can deal an additional 1d6 damage with an attack. You may only use this ability if you have advantage on the attack or if an ally is within 5 feet of the enemy.

Gutter Speak (Level 1): You speak the secret mix of signs, jargon, and code that allows you to communicate with fellow pirates and thieves. You also understand the signals that they leave to inform or warn their fellow rapscallions.

Exit Stage Left (Level 2): You can take a bonus action on each of your turns in combat to dash, disengage, or hide.

Vital Strike 2d6 (Level 3)

Sucker Punch (Level 3): You have advantage on attack rolls against creatures that haven’t taken a turn in the combat yet. Any hit you score against a surprised creature is a critical hit.

Ability Score Improvement (Level 4)

Vital Strike 3d6 (Level 5)

Now You See Me… (Level 5): When you are hit with an attack, you can use your reaction to halve the attack’s damage against you.

2 Additional Specialist Skills (Level 6)

Vital Strike 4d6 (Level 7)

…Now You Don’t (Level 7): When you are subjected to an effect that allows you to make a Dexterity saving throw to take half damage, you take no damage if you succeed and half if you fail.

Ability Score Improvement (Level 8)

Vital Strike 5d6 (Level 9)

Many Faces (Level 9): You may spend seven days and 25 gp to construct a false identity for yourself. You establish, history, profession, and affiliations, along with all the appropriate belongings for that identity. Others will believe you to be that person until given an obvious reason not to.

Ability Score Improvement (Level 10)

Vital Strike 6d6 (Level 11)

Professional (Level 11): Whenever you make an ability check that lets you add your proficiency bonus, you can treat a roll of 9 or lower as a 10.

Ability Score Improvement (Level 12)

Vital Strike 7d6 (Level 13)

A Bit Clangy, A Bit Jammy (Level 13): After studying another person for three hours you can unerringly mimic their speech, writing, and behavior. Your ruse is indiscernible to the average person; if someone is suspicious, you have the advantage on any Deception (Charisma) checks to persuade them otherwise.

Child of the Shadows (Level 14): If you are able to hear, you are aware of the location of any hidden or invisible creature within 10 feet of you.

Vital Strike 8d6 (Level 15)

Devious (Level 15): You gain proficiency in Wisdom saving throws.

Ability Score Improvement (Level 16)

Vital Strike 9d6 (Level 17)

Get the Drop (Level 17): During the first round of any combat you may take two turns, one at your initiative and one at your initiative minus ten.

Slippery Little Bastard… (Level 18): No attack roll ever has advantage against you.

Vital Strike 10d6 (Level 19)

Ability Score Improvement (Level 19)

Pirate! (Level 20): Once a day, you can turn a miss into a hit, or a failed ability check into a roll of 20.


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