Pirate Captain - 5e monster (CR7ish..) : r/UnearthedArcana

The Ringmaster [5e] - An Attitude Era Pro Wrestler Class for 5e : r/ UnearthedArcana

Katherine Jade, Pirate Captain. Is this a good final boss for a party of 6-8 level 5 adventurers? : r/UnearthedArcana

The Freebooter class. A Pirate-themed class where the subclasses each represent a different lifelong goal. : r/UnearthedArcana

Somanyrobots' Swashbuckler [v0.9 Update]! A nimble martial who's equally skilled with rapier, pistol, or quip! Fight with flair as a Duelist, Pistolier, Trickster, Ruffian, or the brand-new Inquisitor! : r/ UnearthedArcana

The Incarnate v1.5 : r/UnearthedArcana

3D Printable Captain Ahathid Set / Mind Eater Pirate / Monster Ahab Collection by Epic-Miniatures

Pirate Class Official

Pirates detail choosing walk-up songs

The Buccaneer v3.0 A Full Class version of the Swashbuckler : r/ UnearthedArcana

A fearsome ogre pirate captain with an intimidating glare on Craiyon

Pirate Captain's Hat, wondrous item (headgear)

To be a Pirate: A Guide for the Inept - Become wannabe pirates in this new 80-page full-conversion supplement for D&D 5e : r/UnearthedArcana