Little is known about the early history of the region. At one time it was part of the now-lost kingdom of Ghol-Gan. There are many ruins of an ancient civilization, which left behind disturbing carvings depicting cannibalism and blood sacrifice.
Few scholars know that several millennia after the collapse of Ghol-Gan, two powerful sorcerers known as Raugsmauda and Gray Whyrlis came to the Shackles and fought one another for control of the archipelago. They both uncovered the powerful sorceries that caused the doom of Ghol-Gan and attempted to harness them. In the end, however, the sorcerers failed to understand and control the powers they were using. In a disastrous incident Gray Whyrlis lost and Raugsmauda, heavily injured, was forced to retreat into her dungeon on Motaku Isle for centuries.
When the region was discovered by explorers from Cheliax they declared it to be cursed, and moved on to establish a colony further south in Sargava instead. As trade grew between Sargava and Cheliax, it attracted those who wished to prey upon it. Pirates found the ancient harbours of the Shackles made excellent hiding places from which to strike. Soon these havens grew into proper communities. Retired sea captains also founded the settlement of Bloodcove in the Mwangi Expanse.
The creation of the perpetual storm known as the Eye of Abendego permanently disrupted the sea trade in the region. The Free Captains met this challenge by banding together in 4674 AR to form one pirate fleet, under the leadership of the newly elected Hurricane King. They started preying on shipping to the north of the Eye, as far as the Arch of Aroden. When they are pursued by foreign ships the pirates skirt the edge of the Eye, using their superior skill and local knowledge to escape their enemies.
In an ironic twist of fate, the pirates now receive a hefty tribute from Sargava in return for protecting the independence of the former colony of Cheliax. The Shackles themselves have twice been attacked, once by Cheliax and once by Rahadoum, but in both cases the Eye destroyed most of the invading fleet. There is a rumour that one of the Free Captains has offered to guide a Cheliax fleet to the Shackles, in return for a pardon for past offenses. It is also known that the Rahadoum navy is willing to pay good money for accurate charts, or ideally a pilot, to assist them in a new attack on the Shackles.