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Drakosa owned a plantation near Helmsport.
Arriving in Helmsport, Drakosa bought a plantation from Jalimar Trollslayer, one of the original soldiers of the Golden Legion. He was capable in managing the plantation, raising tobacco and indigo.
In 1362 DR, he hired an adventuring party to find the Cloak of One Plume in order to give it to Cordell to gain his favor. He sent his two servants Hasoctl and Ironspike with the adventurers to check up on them.
Drakosa was a relatively lenient master with his slaves, using force only when truly necessary. He dreamed of becoming governor of his own region. He plotted to achieve this goal by manipulating factions like the merchants, the soldiers, and even the Payit. He also dreamed of finding a large amount of gold but cared too much for his own life to go on adventure himself. In his mind, the adventurers existed for this purpose.