Chicago is a series of paradoxes and transitions, of ever-changing paradigms and whimsy. It is both beautiful and putrid, both corrupt and a pillar of truth, an unstoppable force for change while holding onto the past with howling desperation. Chicago’s inherent dichotomy is reflected in the people, buildings, neighborhoods, history, and, most definitely, in its vampires.
Vampires have haunted Chicago since before the city even existed: in the 17th century, the vampire "Pale Wolf" (actually the Brujah Methuselah Menele) took refuge in the region during his flight from his nemesis, the treacherous Toreador Helena. The two ancients fought, and both were forced into torpor; Menele was hidden by his Native American childe and ghouls with the assistance of the Uktena, and Helena was secreted away by her own ghoul, Prias. Each of the slumbering Methuselahs used their influence over their respective broods (via the blood bond and mental Disciplines) to manipulate the development of the settlement that became Chicago. Menele took advantage initially, as he was able to instill his clanmate (and pawn) Maxwell as the city's first Prince. Despite that victory, the two sleeping ancients continued to battle via proxies, particularly the city's primogen. Helena won a major victory when the Great Chicago Fire broke out: her catspaw Lodin was able to force Maxwell out, take the office of the prince for himself, and install his childer in positions of influence across the city. Lodin's domain eventually encompassed Gary, Indiana, and had tendrils in Milwaukee.