How does a poor, single, African-American mother from segregated 1950s America wind up as one of the worlds most notorious jewel thieves? A glamorous 81-year-old, Doris Payne is as unapologetic today about the nearly $2 million in jewels she's stolen over a 60-year career as she was the day she stole her first carat. With Payne now on trial for the theft of a department store diamond ring, filmmakers Kirk Marcolina and Matthew Pond probe beneath her consummate smile to uncover the secrets of her trade and what drove her to a life of crime. Romanticized recreations, an extensive archive and candid interviews reveal how Payne managed to jet-set her way into any Cartier or Tiffanys from Monte Carlo to Japan and walk out with small fortunes. This sensational portrait exposes a rebel who defies society's prejudices and pinches her own version of the American Dream.