Skull & Shackles
When a Free Captain named Magna Stormeyes discovered the natural harbor on Windward Isle over 2 centuries ago, she immediately recognized that it would make the perfect haven from which to launch a pirate fleet. Starting with just one ship and a small encampment on Windward’s harbor, she began to ply the trade of piracy. With the plunder from her initial hauls, she set about building a keep, which she called Tidewater Rock. From the vantage point atop the Rock, she found she could pick out particularly ripe targets while receiving ample of warning of hostile ships approaching.
Over time, Stormeyes’ successes enabled her to build a sizeable fleet, as well as more strongholds on several different islands. She became the scourge of the southern sea lanes and eventually relocated to Port Peril, where she was assassinated by rival Free Captains shortly thereafter. Stormeyes’ burgeoning fleet then fell apart among its squabbling captains.