The Masquerade

A middle-aged male Kindred Ventrue with slicked-back salt-and-pepper hair, a manicured beard, and sharp tailored suits that are too flashy for his company. He wears Armani shoes and a gold chain, carrying an overconfident swagger.

Bobby is slick, charismatic, and intentionally gaudy, a master of charm, misdirection, and double-speak. He is a calculating survivor who believes in power, influence, and the art of the long con. He makes friends easily and betrays them only when necessary, always making it feel like it wasn’t personal. He is both maddening and hilarious, with a relentless energy that commands any room he enters.

Bobby Weatherbottom was Embraced in the early 2000s during his peak as a high-powered real estate developer and media personality. Known for flipping blighted properties and revitalizing communities on Chicago's South Side, he gained notoriety for lining his own pockets. The Ventrue clan saw in him a modern capitalist knight: ruthless, presentable, and media-savvy. His Embrace was both a reward and a leash, but Bobby is a pragmatist who doesn't wear leashes well. Caught between the rising Anarch unrest and a paranoid Camarilla, he chose to work both sides, becoming a broker of secrets and influence. Officially loyal to the Camarilla, unofficially he is a valuable and untrusted informant to the Anarchs.