The Winchesters are best known for being America’s most elusive dynasty. Charlie Winchester is a rich girl. She has always been a rich girl. But her family's baggage comes with a price, and theirs is designer. When Charlie's mother died unexpectedly seven years earlier, her family was left fragmented beyond repair. She has spent the years since her mother’s death running from the family she can’t seem to mend and the legacy she wants to escape. Forced to return home to Chicago after years of trying to avoid fixing herself by helping others, Charlie attempts to carve a name for herself and her own path at Winchester Holdings: their family of generations' company. Although she has never had much success in the dating department, unlike her brother Deacon whose life is an endless parade of dates and conquests, Charlie is surprised to find herself enamored with one of her colleagues. That is until someone from her past she attempted to bury along with her mother appears back in her life and turns everything she has worked to create upside down.