Scoundrel (Pirate) — D&D 5.5e (2024 Rules)

3rd Level: Salty Seadog Cant and the Pirate Code

You know the secret language of pirates and seasoned sailors. You can speak, read, and write in Salty Seadog Cant, allowing you to communicate hidden messages and meanings with other pirates, smugglers, and maritime rogues. This language uses a combination of nautical terminology, coded phrases, and subtle gestures that appear as normal sailor talk to outsiders.

You also understand the Pirate Code, a loose set of maritime guidelines that govern pirate behavior and honor among thieves. The Code includes principles such as:

• Any pirate may invoke parley to speak directly with the captain
• Every crew member has a vote in matters of moment
• Equal share of provisions and plunder for all hands
• Captain gets double share of plunder
• Quarter to be given when asked for (surrender must be honored)
• No striking another crew member aboard ship (disputes settled ashore)
• Quarrels to be ended on shore with sword and pistol
• Mutiny against the captain is punishable by death
• Desertion during battle is punishable by death or marooning
• Marooning for serious crimes (left on desert island with pistol and shot)
• Theft from fellow crew members earns fifty lashes
• Keep weapons clean and ready for action
• No gambling with dice or cards for money aboard ship
• No women aboard ship except for pirates
• Lights and candles out by eight o'clock at night
• Compensation for injuries sustained in service (200 gold pieces for right arm, etc.)

However, as any seasoned pirate knows, the Code is more what you'd call "guidelines" than actual rules. When interacting with other pirates who follow the Code, you have advantage on Charisma checks to negotiate, parley, or invoke maritime law. Additionally, you can use your knowledge of pirate customs to predict how other pirates might behave in certain situations.

3rd Level: Improvised Tools

Your life of piracy has taught you to make do with whatever is at hand. You can use improvised items as if they were proper tools for certain tasks. As an action, you can designate one mundane object within reach as an improvised tool for one of the following purposes:

• Thieves' Tools: Use a hairpin, nail, or similar small object
• Navigator's Tools: Use a stick, rope, or celestial observation
• Tinker's Tools: Use scrap metal, nails, or ship materials
• Rope/Grappling Hook: Use bedsheets, belts, or furniture

When using improvised tools this way, you do not have proficiency with the tool, but you can still attempt the task without the usual disadvantage for lacking proper equipment. The improvised tool breaks or becomes unusable after one use. You can use this feature a number of times equal to your Intelligence modifier (minimum of once), and you regain all expended uses when you finish a long rest.

3rd Level: Enhanced Mobility

Your incredible agility and natural grace make you perfectly suited for maritime adventures. You gain a climbing speed and swimming speed equal to your walking speed, and you have advantage on Dexterity checks made to maintain your balance.

3rd Level: Devil's Own Luck

Your supernatural luck keeps you alive in impossible situations. You have a pool of luck dice equal to your proficiency bonus, and you regain all expended luck dice when you finish a long rest. Your luck die is a d6. It becomes a d8 at 9th level, a d10 at 13th level, and a d12 at 17th level.

When you make an attack roll, ability check, or saving throw, or when a creature makes an attack roll against you, you can use your Reaction to expend one luck die. You can add the result to your roll or subtract it from an attack roll made against you. You can choose to use this feature after you roll the d20, but before the DM says whether the roll succeeds or fails.

Additionally, you have advantage on death saving throws, and when you roll a 20 on a death saving throw, you regain 1 hit point and can immediately stand up without expending movement.

3rd Level: Roguish Charm

Your natural charisma and roguish appeal make you irresistible to many. You gain proficiency in Deception and Persuasion if you don't already have them. If you're already proficient in either skill, you instead gain expertise in that skill.

Additionally, you can use your bonus action to attempt to charm a humanoid within 30 feet that can see and hear you. The target must make a Wisdom saving throw (DC = 8 + proficiency bonus + Charisma modifier). On a failure, the target is charmed by you for 1 minute or until you or your allies harm it. While charmed this way, the target has disadvantage on attack rolls against you. You can use this feature a number of times equal to your Charisma modifier (minimum once), and regain all uses when you finish a long rest.

"But You Have Heard of Me." When you dramatically reveal your identity or reputation to creatures who might know of your exploits, you have advantage on the next Charisma check you make against them. The DM determines whether creatures would reasonably know of your reputation based on your adventures and notoriety.

9th Level: Impossible Escape

You've perfected the art of getting out of trouble through a combination of luck, agility, and split-second timing.

Narrow Escape: When you would be reduced to 0 hit points by an attack, you can use your reaction to expend a luck die and instead drop to 1 hit point. When you do so, you can immediately move up to your speed without provoking opportunity attacks, and you must describe how you barely escaped (sliding under something, swinging on a rope, etc.). Once you use this feature, you can't use it again until you finish a long rest.

Slippery: Opportunity attacks against you are made with disadvantage, and when you take the Dash action, you can move through the space of any creature.

13th Level: Lucky Break

Your luck extends beyond mere survival to create opportunities from disaster. When you roll a 1 on an attack roll, ability check, or saving throw, you can choose to have something fortuitous happen instead. The lucky break shouldn't directly defeat enemies or replicate the effects of a spell of 5th level or higher. Work with your DM to determine an appropriate lucky break:

• A chandelier falls, creating difficult terrain for enemies
• You "accidentally" discover a secret door or hidden passage
• An enemy's weapon gets stuck or breaks
• You find exactly the item you need in your pocket
• Environmental conditions shift in your favor

You can use this feature once per long rest.

Additionally, when you expend a luck die and roll the maximum number on the die, you don't expend the die (you still get the bonus, but keep the die).

17th Level: Legendary Luck

Your reputation for impossible escapes and miraculous survival has become the stuff of legend. You gain the following benefits:

Cursed Instincts: Your countless encounters with supernatural forces have given you an intuitive understanding of curses and their nature. When you encounter a curse, cursed object, or cursed creature, you instinctively know the general method required to break or lift the curse (such as "destroy the source," "perform a specific ritual," "fulfill a condition," etc.). This knowledge doesn't provide the specific details, components, or means to accomplish the task, but gives you the conceptual framework of what must be done. Additionally, you have advantage on saving throws against curses.

Fate's Favorite: Once per turn when you roll damage for a Sneak Attack, if you roll the maximum number on any damage die, you can roll one additional die of the same type and add it to the damage. You can only do this once per maximum die you roll.

Miraculous Timing: When you roll initiative, you can expend all remaining luck dice to take an additional action on your first turn. You regain one luck die for each enemy you can see when you use this feature (up to your normal maximum).

Nine Lives: When you fail a death saving throw, you can expend a luck die to turn it into a success instead.