The Jacksonville Monster:Donald Smith·Cherish Perrywinkle

Donald James Smith, 56, was a registered sex offender with a long record of crimes against children. He had been out of jail for only about three weeks when, on June 21, 2013, he met Rayne Perrywinkle and her three daughters at a Dollar General in Jacksonville, Florida. He offered to buy the girls clothes and drove the family to a nearby Walmart.

Late that night, Smith took eight-year-old Cherish toward the store’s McDonald’s counter, saying he would get food, and instead walked her out to his van and drove away. Rayne called 911, and security video gave police a clear image of Smith and his vehicle. Officers stopped him on Interstate 95 the next morning. Hours later, Cherish’s body was found in a wetland behind Highlands Baptist Church. She had been sexually assaulted and strangled.

In February 2018 a jury convicted Smith of first-degree murder, kidnapping, and sexual battery after deliberating for only minutes, and on May 2, 2018, Judge Mallory Cooper sentenced him to death. The Florida Supreme Court upheld the conviction and sentence in 2021, and the U.S. Supreme Court declined to hear his appeal in 2022. A Duval County judge rejected his request for a new trial in 2024, and the Florida Supreme Court heard his appeal of that ruling in December 2025.