Last year, Whitfield Leland, a failed democratic mayoral candidate, was arrested after an armed robbery at a Dollar General store. According to police documents, he took a Dollar General Shirt in an attempt to disguise himself as an employee. However, he ran out of the store after stuffing his pockets with cash shortly before being apprehended by police.
Authorities initially thought he was an employee at the store based on the shirt he was wearing. However, after a short foot chase, he was apprehended behind a local church. Leland stole an unknown amount of money during the robbery. His political campaign was just as much of a failure as his brief criminal career. His mayoral campaign was decidedly unsuccessful.
Leland ran for Tallahassee mayor in 2022. He came in a distant third place in a four-man primary and gathered less than 5% of the vote. He also played a minor role on the campaigns of Rudy Ferguson. Ferguson paid him $65 for help on a City Commission race. Kenneth Preston, who ran for Leon County property appraiser, paid him another $110.
Officers followed a trail of cash to his hiding place in a wooded area. The Democrat was arrested and charged with multiple serious crimes. He was charged with robbery with a firearm, grand theft of a firearm, possession of a firearm by a convicted felon and resisting an officer without violence. After his arrest, Leland was held in Leon County Detention Facility.
Trinyan Mariano, who witnessed the events, said officers swarmed the scene of the crime. Within a few moments, the police had the store surrounded. While looking for evidence, officers found the discarded gun used in the robbery. Court records state that a customer called 911 after Leland pulled a gun on the manager before sprinting out of a fire exit.
The manager, who was “shaken” and “in fear for his life at the time of the incident,” gave a statement to the police. He said that Leland tried to hold up the store and ordered him to open the registers. After he ordered the manager to lay down, he changed his mind and instructed him to open the safe. However, “the safe was delayed and would not open right away.”
However, this is not Leland’s only run in with the law. In 2019, he was arrested and sentenced to 90 days in jail for resisting arrest. During the arrest, which took place at a local fairgrounds, an officer said Leland was “belligerent” and “screaming at us.” He testified that Leland attempted to kick the window out of the patrol car after his arrest.
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“He swung on me, he swung on me,” the failed candidate repeated. He argued with officers that another partygoer started a fight. “I’m not leaving,” insisted, “I want to file a report.” Leland also asked to speak with a supervisor and then the Leon County Sheriff. After they loaded him into the cruiser, one officer can be heard saying, ” He caught me in the lip,” as Leland impotently flailed.