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Pirates expands the familiar cutlass-and-bandit trope into a full, encounter-ready hierarchy designed for 5e play. Rather than treating pirates as a single low-level threat, this supplement presents a complete ladder of shipboard roles, hardened crew, disciplined officers, and infamous commanders—from powder monkeys and deckhands to captains, admirals, and legendary terrors of the coast—each built to fill a specific role at the table.

Whether you need disposable crew to crowd a boarding action, aggressive specialists to control rigging and firing lines, veteran enforcers to hold the deck under pressure, or a climactic pirate lord commanding the fight itself, Pirates provides mechanically distinct stat blocks at every tier of play. The ladder is designed to scale naturally, allowing pirate encounters to grow from chaotic skirmishes into full naval battles and campaign-defining confrontations. Firearms and artillery are fully supported through existing 5e rules, keeping the focus on tactics, positioning, morale, and leadership rather than magic.

Each pirate type is designed with clear battlefield purpose, strong internal synergy, and GM-friendly abilities that emphasize coordination, intimidation, and ruthless efficiency. Use them as freebooters, privateers, naval raiders, criminal fleets, or feared legends of the sea—the structure is provided, the flag they fly is yours.

Pirate Ladder

Pirate Powder Monkey (CR 0): Noncombatant youth who carries powder and shot. Their injury or death often provokes violent reactions from nearby crew.
Pirate Deckhand (CR 0): Sailor or laborer without formal combat training, armed only with tools or improvised weapons.
Pirate Cabin Boy (CR 1/8): Young shiphand armed with a knife. Quick and nervous, more likely to flee than fight.
Pirate Dock Ruffian (CR 1/8): Shore-side thug accustomed to brawls and ambushes but lacking discipline.
Pirate Crewman (CR 1/4): Standard pirate armed with a cutlass and sidearm. Fights best in groups.
Pirate Boarding Hand (CR 1/4): Aggressive melee fighter trained to grapple, shove, and overwhelm enemies during boarding actions.
Pirate Gunner (CR 1/2): Crew member trained with pistols or muskets, providing deadly ranged fire before closing in.
Pirate Rigging Fighter (CR 1/2): Agile skirmisher who uses ropes and rigging to gain height, mobility, and positional advantage.
Pirate Swashbuckler (CR 1): Mobile duelist who relies on speed, footwork, and opportunistic strikes.
Pirate Grenadier (CR 1): Specialist who uses black powder bombs, fire pots, and smoke to disrupt formations.
Pirate Harpooner (CR 2): Heavy melee combatant who uses barbed weapons to restrain, pull, or drag enemies.
Pirate Quartermaster (CR 2): Veteran organizer who controls supplies and morale, bolstering nearby allies through command and discipline.
Pirate Veteran (CR 3): Hardened survivor of countless battles, capable of parrying blows and pressing the attack.
Pirate Boarding Sergeant (CR 3): Front-line leader who directs crew movement and coordinates assaults.
Pirate Master Gunner (CR 4): Expert artilleryman who controls cannons and heavy shipboard weapons with deadly efficiency.
Pirate First Mate (CR 4): Trusted second-in-command who coordinates crew actions and reacts swiftly to threats.
Pirate Champion (CR 5): Elite duelist renowned for personal combat prowess and fearlessness.
Pirate Shock Trooper (CR 5): Brutal enforcer trained to smash enemy lines and seize control of key positions.
Pirate Bosun Enforcer (CR 6): Officer who maintains discipline through intimidation, punishment, and ruthless example.
Pirate Veteran Captain (CR 6): Experienced ship captain skilled in tactics, positioning, and crew coordination.
Pirate Captain (CR 7): Charismatic leader whose presence inspires allies and breaks enemy resolve.
Pirate Dread Privateer (CR 7): Licensed raider who combines military discipline with merciless efficiency.
Pirate Iron Captain (CR 8): Heavily armored commander who dominates firefights and close-quarters combat alike.
Pirate Reaver Lord (CR 9): Infamous pirate leader whose reputation alone can unnerve seasoned foes.
Pirate Warlord (CR 10): Supreme commander of multiple crews, capable of directing large-scale engagements.
Pirate Fleet Admiral (CR 11): Master of naval warfare who commands ships, artillery, and disciplined crews with precision.
Pirate Terror of the Coast (CR 12): Legendary pirate whose name is synonymous with devastation, fear, and total control of the battlefield.

Compatible Products

Pirate Cove: Maps designed for pirate encounters and adventures.

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