The Night of the Unwanted
The independent costal city of Freeport is well known by many to be a haven for the criminals of Thea, coming to hold the largest and most organized thieves guild on the continent. Though based in the southern city, their activities stretch to nearly every kingdom on the continent. Because of this, guild members often find themselves in a position to fresh prospective talent for the group in the form of the many orphaned children of the continent. These 'Unwanted' are taken in by the guild in exchange for small work, running errands or acting as lookouts during heists. The few that show great promise in the illicit arts are trained further in them by a mentor from the guild.
Once a year, in Freeport, mentors may send their charges to participate in the Night of the Unwanted, a sort of right of passage for the orphaned children to gain full membership into the orginization.
Execution
For the Night of the Unwanted, each participant is given a specific item that they are tasked with retrieving, ideally without detection. The only information they are given is the objects description and location. It is then up to each participant to research, formulate and enact their retrieval. In the past objects have ranged from mundane trinkets planted by their mentor, to articles of royal jewelry, and have been hidden in nearly every corner of the continent, often making the 'night' last several months due to travel and planning times.
The degree of difficulty of a successful heist tends to determine the prestige within the guild gained by the participant upon completion, so there is a tendency toward grander and grander conquests.
Successful participants of the Night of the Unwanted often continue on to become high ranking, and skilled members of the Thieves Guild.
Observance
While the exact start of the night of the unwanted is unknown to those outside the guild, it is commonly thought to begin sometime around mid-spring, giving fairer weather for travelling than in winter or the height of summer.
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Oooh local orphan theft night. I like it :)