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Simon Trenante was an unlikely choice for Sheriff of London after the former holder of the post perished in Coven's rebellion. Granted, he was a fairly potent elder, but he was also widely seen as a self-absorbed dilettante, lacking the self-discipline or attention to detail to keep order among the city's Kindred. Some cynics suspect that resistance to his appointment was muted precisely because most of London's vampires preferred him to a (perhaps) more effective and activist candidate.
And it's true that he hasn't displayed any great diligence since taking office, preferring to devote himself to his own domain of Soho and his connections with the city's drug trade. Yet, more perceptive observers note, Kindred society in London seems to run suspiciously smoothly considering that it has a mad Prince and an indolent Sheriff.
He first appeared in London, as far as most of its Kindred know, in the wake of the Great Fire in 1666. He was sponsored by the then Gangrel Primogen, the ancient Chalice of Mercia, and was widely suspected to be her childe. He used the nickname "the Black Friar" from his earliest nights in London, although he never explained why. He rapidly established himself among the city's criminal population, especially its more transient elements - the smugglers who worked out of its docks, the highwaymen who haunted the roads around, the vagrants and beggars who roamed its streets, and some of its more disreputable troupes of itinerant actors. As Mithras had almost certainly intended, that brought him into conflict with the Jackdaw, who as always saw London's criminal element as his own exclusive domain. The Jackdaw almost pushed Trenante out of the city altogether after Mithras disappeared in 1798, but the victory was a relatively fleeting one, as the Prince was quick to re-instate the Gangrel on his return. After the Jackdaw fell into torpor in 1937, Trenante expanded his influence into city's burgeoning drugs trade, which gave him a connection to the moneyed elite of London's financial district as well. By the time of Coven's attempted coup, he was powerful enough to command a measure of respect, but seen as largely apolitical, with few allies, and crucially, no significant enemies. As such, he made a plausible compromise candidate for Sheriff, someone who was unlikely to use his power to prosecute old feuds or promote favorites.