Michael Cassius McDonald arrived in Chicago as a teenage scam artist who quickly sketched a blueprint for running the city through its criminal underworld. Chicago's original mob boss, he procured presidential pardons, stuffed mayoral ballot boxes and operated the town's plushest gambling parlor. But he was also a philanthropist who befriended Clarence Darrow, employed Theodore Dreiser, promoted the World's Fair and funded the Lake Street L. His scandalous private life mirrored the tumult of his career, with more than one marriage mired in a love triangle and a murder trial. Kelly Pucci charts the rise of Chicago's first kingpin.