"Friend of the Brass Monkey", 5e Rogue/Thief variant
by Marc SaindonA bit of fan-made lore here: there once was a great thief known only as 'the Brass Monkey' who would steal from the rich and give to the poor. Yes, he's much of the Iron Monkey and Robin Hood type of character, with Zorro and Arsene Lupin thrown into the mix. The Brass Monkey would often do spectacular heists, targeting corrupt officials and aristocrats in need of humility. He would steal priceless heirlooms and leave a small brass statuette of a monkey, or paint a monkey on the wall (an orange paint stencil similar to the 'barrel of monkeys' toy ). Rapidly, he developped a cult following among the poor, and gained a high price on his head by authorities. Eventually, the magistrates caught up with him and he died during a purge.
Naturally, like all legends, the Brass Monkey went on to live just like Elvis. The thing is that in order to pull off his heists, the B.M. would use a lot of misdirection, including having several companions impersonate him, in order to be everywhere at once and have convenient alibis at the moment of the heist. When the magistrates purged the Brass Monkey and his associates, one survived, and fled. The survivor slowly healed in seclusion, and over the years rebuilt the network necessary to pull off the previous schemes. For a time, he claimed to speak on behalf of the Brass Monkey to his allies, but eventually after several decades, he pulled off a 'Pirate Roberts' (see the Princess Bride movie) and presented himself as the Brass Monkey to younger recruits (his inner circle was aware and complicit in the ruse). Many years later, the lone survivor died, passing on the mantle of the Brass Monkey to a member of the inner circle and this tradition has persevered for generations.
'Friends of the Brass Monkey' are rebels, but good-hearted thieves, leaning towards Chaotic Good. They operate like a Thieves' Guild or a Triad, but their core ideology is anti-authoritarism and the rights of the common man. They focus on theft and fraud (with the rich as their main target), avoiding the more violent crimes and the debasement of vice trade. They may also indulge in various "publicity stunts" that embarass corrupt officials. While not as powerful as a Triad, they do have popular support among the populace, peasants will not likely denounce an agent of the Brass Monkey to the town guards.
The Level-named characters (9th level in BECMI, 10th in 5e) form the Inner Circle, and are among the few who know the secret about the Brass Monkey as a fictive leader of the group. Alternatively, popular belief in the Brass Monkey might possibly raise him back as a mischievous lesser deity or spirit, a bit like an Ancestor or City God in Chinese myth.
(Image from: https://www.deviantart.com/rotaken/art/Thief-565848959)