A day in the life of a Chicago cab driver is examined as he picks up fares from the good and bad parts of the city and emotionally connects to many of his passengers.

Season 1 depicts the whirlwind courtship and marriage of John F. Kennedy Jr. and Carolyn Bessette. What started out as a beautiful union for the young couple, widely regarded as American royalty, began to fray under the stress of the relentless microscope and navel gaze of tabloid media.