Jacqueline "Jackie" Li Woodruff was born to Jack and Lillian Li on November 17, 1995, in Oxford, Mississippi. Her parents, a couple in their thirties, immigrated from mainland China in the mid-1980s. Jackie is their only child.
Former teachers remember Jackie's infectious laugh and how quickly she raised her hand in class, even if she didn't know the correct answer. In her senior yearbook, she was named "Most likely to move to Hollywood." She was a member of various local acting companies from the age of seven and a featured player in her high school drama club.
After graduation, she worked several jobs so she could afford to launch her acting career. While waiting tables in a full-service restaurant that no longer exists, she met Henry Woodruff, who tended bar there on weekends. They dated for several months and then married when Jackie discovered she was pregnant. Daughter Kennedy was born seven months later and then son Bruce the following year.
Jackie stayed with the children during the day while her husband worked as a computer technician at Mississippi Casualty and Life. Once Henry came home from work, Jackie left the children in his care and headed to her waitressing job so the family could make ends meet. Ex-employers speak highly of Jackie and describe her as a valued team member who was always there for the other servers.
On February 15, 2019, Jackie brought a necklace to County Pawn and received $25 with her ticket. The necklace later appeared on a list of stolen goods circulated by the Yoknapatawpha County Sheriff's Department, and the pawnshop owner called the department to report the incident.
When the officers arrived to pick up Jackie for questioning, they found her at home with her two children, and they arranged for a neighbor to come over until her husband returned from the office. Numerous witnesses testified that they saw Jackie repeatedly strike the officer who was trying to separate her from her little girl.
According to Jackie, a customer left the necklace as a tip. He said it was intended to be a Valentine's Day present for the date who stood him up. Jackie said she hadn't told the other servers because she didn't want to start a rumor that the mystery customer had been a boyfriend, and she didn't tell her husband what happened for the same reason.
Jackie was charged with possession of stolen property and assault on a police officer. The family hired Robert Pruitt to defend her. Despite Pruitt's efforts, Jackie was found guilty of the charges and sentenced to one year in prison. Jackie reportedly was a model prisoner, and her husband visited her weekly.
Soon after Jackie was released on September 17, 2020, the Law Offices of Pruitt & Rayburn resumed their efforts to collect an unpaid bill for her legal defense. Jackie had been unable to find a job because of her felony conviction, so she refused to pay. The law firm sent her a registered letter promising that the matter would be turned over to a collections agency if she did not pay in sixty days.
Jackie went to the office and demanded an audience with Robert Pruitt. Her request was denied, so Jackie called every day for two weeks until they told her that the sheriff's department would be notified if she continued the harassing behavior. Jackie's response was abusive, but the telephone calls ceased.
Frustrated by her family's mounting debts, Jackie told friends that she'd smacked around the wrong person. Instead of hitting the officer who had only been doing his duty, she should have saved her energy for Pruitt, who didn't know the first thing about his job.
The other pieces stolen at the same time as the necklace have never been recovered, nor has anyone ever been charged for the burglary. Jackie has never stopped maintaining her innocence on the original possession charge.