Dread Pirate

Level Special
1st Weapon and Armor Proficiency. Seamanship, two-weapon fighting
2nd Fearsome reputation, Rally the Crew, or Sneak Attack +3d6
3rd Acrobatic Charge, Steady stance
4th Luck of the wind or scourge of the seas, Acrobatic Mastery
5th Fight to the Death or Motivate the Scum, Pirate King

Thugs and cutthroats in every port lay claim to the title “pirate,” but actually making a fortune through piracy is no easy task. A dread pirate, however, has mastered every aspect of larceny on the high seas.

Some dread pirates accomplish their goals through fear, killing indiscriminately and ruling their ships at rapier-point. Others minimize bloodshed and exhibit a curious sort of chivalry, perhaps realizing that the captain and crew of a prize ship are more likely to surrender if they believe they will live to see port again. Now and then a dread pirate takes his chivalric streak a step farther and preys only on the ships of enemy nations—or even solely on other pirates.

A dread pirate’s lifestyle is ideal for most rogues, because the job requires a number of skills that other classes don’t have the time or inclination to learn. However, the class also attracts some spellcasters, who can use magic to conceal their ships or incapacitate a prize vessel’s crew.


Level: Fourth level

Alignment: Any nonlawful.

Skills: Athletics, Vehicles (water)

Special: The character must own a ship worth at least 10,000 gp. The method of acquisition—purchase, force of arms, or skullduggery—makes no difference, as long as he can freely operate it on the high seas.

Hit die: D10

Class Features

Weapon and Armor Proficiency: Dread pirates are proficient with all simple weapons, with light martial weapons, and with the rapier. Dread pirates are proficient with light armor but not with shields.

Seamanship: A dread pirate gains expertise (allowing double proficiency roll) in his Vehicles (water) checks and his crew if within shouting distance have advantage to any Vehicles (water) checks they need to make.

Two-Weapon Fighting: When you engage in two-weapon fighting, you can add your ability modifier to the damage of the second attack.

Fearsome Reputation: By the time he attains 2nd level, a dread pirate has developed a reputation on the high seas. At this point, he must choose whether to cultivate a reputation as an honorable pirate (avoiding undue bloodshed, honoring flags of truce, and the like) or as a dishonorable pirate (favoring mayhem and dire treatment of prisoners).

An honorable dread pirate gains an advantage bonus on Persuasion checks, while a dishonorable one gains an advantage bonus on Intimidate checks.

A dread pirate’s actual activities or alignment need not match his reputation. However, a radical shift away from his reputation might negate or even reverse that reputation at the DM’s option. Also, a dread pirate in disguise does not gain any effect granted by his reputation (including the special abilities described below that depend on the dread pirate’s reputation).

Rally the Crew: Starting at 2nd level, an honorable dread pirate can inspire his allies (including himself) to great bravery in combat once per day. This inspiration grants them an advantage bonus on saving throws against charm and fear effects and a +3 morale bonus on attack rolls and weapon damage rolls. To be affected, an ally must be able to see or hear the dread pirate. The effect requires a bonus action to activate and lasts for 1 minute per class level, even if the dread pirate moves out of range or loses consciousness. This is a mind-affecting ability.

Sneak Attack: Starting at 2nd level, a dishonorable dread pirate deals an extra 3d6 points of damage to his sneak attack damage. If he does not have the sneak attack class feature he gains it as a Rogue.

Acrobatic Charge: A dread pirate of 3rd level or higher treats all rough terrain on a ship as normal terrain.

Steady Stance: At 3rd level you gain advantage to athletics and acrobatics checks made required to stay stable on a ship.

Luck of the Wind: Once per day, an honorable dread pirate of 4th level or higher can reroll any failed attack roll, skill check, ability check, or saving throw. He must take the result of the reroll, even if it’s worse than the original roll.

Scourge of the Seas: Starting at 4th level, a dishonorable dread pirate can instill fear into his enemies. When the character uses Intimidate to demoralize (higher chance for the enemy to surrender or flee from combat) foes, the attempt affects all enemies within 30 feet who can see and hear him, and the effect lasts for a number of rounds equal to his Charisma modifier (minimum 1 round). Multiple uses of this ability don’t stack. This is a mind-affecting ability.

Acrobatic Mastery: At 4th level, a dread pirate becomes supremely confident of his mobility. He has mastered the Acrobatic skill to the extent that he can take 10 with them even under stress.

Fight to the Death: At 5th level, an honorable dread pirate can inspire his allies to carry on against tremendous odds. Each ally affected by the dread pirate’s rally the crew ability (see above) also gains temporary hit points equal to 10 + the dread pirate’s Cha bonus (minimum 10), gains a dodge bonus to Armor Class equal to the dread pirate’s Cha bonus (minimum +1). These effects are lost if the dread pirate loses consciousness.

Motivate the Scum: Once per day, a dishonorable dread pirate of 5th level can motivate his allies by killing a helpless individual. All allies of the dread pirate who see the act gain advantage on attack rolls. This effect lasts for 24 hours. Most dishonorable dread pirates don’t care whether the victim is a prisoner or one of their own crew. In fact, if the slain individual is one of the dread pirate’s crew, the morale bonus advantage to attack rolls, but the allies also take a disadvantage on wisdom saves for the duration of the effect.

Pirate King (Ex): A 5th-level dread pirate’s exploits have become so legendary that great numbers of able sailors are willing to sign on as his crew for no compensation other than a share of the booty. The dread pirate gains the Leadership feat for free.


Most pirate codes share a number of elements regarding the proper “etiquette” of piracy. Here are a few ideas that might be appropriate for your dread pirate’s personal code:

  • Everyone shall obey all orders.
  • Everyone shall have a vote in major decisions. (This point is not necessarily limited to honorable dread pirates.)
  • Everyone shall have a share of captured food and drink.
  • Booty will be shared out as follows: one share to each among the crew; one and one-half shares each to the first mate, master carpenter, and boatswain; and two shares to the captain. (Some honorable captains might accept a smaller share, but they will take no fewer than one and one-half shares.)
  • Anyone not keeping his weapons clean and fit for an engagement shall be cut off from his share, and suffer other punishment as the captain deems fit.
  • Anyone who strikes another among the crew shall receive forty lashes across his back.
  • Anyone who attempts to desert or keep any secret from the company shall be marooned with one bottle of water and one weapon.
  • Anyone who steals from a crewmate shall be marooned or run through. (The latter consequence is more appropriate for dishonorable dread pirates.)