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An earnest man in his late twenties,  Jalester hails from the distant land of Cormyr, where he earned his spurs working for a mercenary company called the Steel Shadows.

A few years ago, Jalester left the Dales and traveled to Waterdeep with several other members of the company. While in the city, he stumbled into and helped thwart a plot to assassinate the Lords of Waterdeep.

He subsequently became an agent of the Lords' Alliance, reporting directly to Open Lord Laeral Silverhand and has remained in that position since, working to uncover threats to the city of Waterdeep and seek out those who might be of service to the good of the city. In this capacity, he holds the title of Captain of the City Watch despite not formally belonging to the organization.

Jalester spends much of his free time in taverns that adventurers are known to frequent.