A 54-year-old South Tampa man has been missing for days after his release from Hillsborough County Jail, and his family says the search has been complicated by suspicious phone calls demanding money and by unusual financial activity on his accounts while he was locked up. David May was last known to be in the 1200 block of Orient Road on August 20, according to police, just a day after he walked out of custody.
May was arrested for trespassing at a downtown Tampa hotel on August 16 and released from Hillsborough County Jail on August 19, according to FOX 13 Tampa Bay. His family reported him missing the very next day, on August 20, after he never returned home. The Hillsborough County Sheriff's Office runs two main detention facilities in the Tampa area — the Orient Road Jail and the Falkenburg Road Jail — and May was booked at Falkenburg Road before his release, which helps explain why his last known sighting near Orient Road struck his family as such a troubling clue.
May's sister, Elizabeth Kieffer, said the family just wants to know he's okay. “We just want you to be safe,” Kieffer said, according to the station's report, adding that her brother should not be ashamed or scared, and that the family only wants to help him. May is described as a white male, approximately 6 feet 2 inches tall and 225 pounds, bald, and possibly sporting a gray beard. Kieffer has said May has faced mental health challenges this year, according to the family.
Suspicious Calls and Unexplained Withdrawals
While May was still jailed, his family noticed unusual financial transactions coming from his accounts — activity they say he did not make himself. Shelley Croft, a licensed private investigator with the volunteer group We Are The Essentials, said financial transactions occurred that were not done by May, per the same account. The family also received a suspicious call requesting money for a monitoring device, and separately found a stranger's belongings and packages left at May's South Tampa home.
The pattern echoes a warning law enforcement agencies and correctional facilities nationwide have issued repeatedly: scammers monitor public arrest logs and call relatives demanding immediate electronic payments for fake ankle monitors or release fees. Since Hillsborough County Sheriff's Office booking records are published online as public records, and newly arrested people get free phone access to reach family from jail, the family says it's left them unsure which calls and packages were genuine and which were attempts to exploit May's arrest.
A Jeep Trail Leads to Lakeland, Then Goes Cold
We Are The Essentials, the Florida nonprofit that launched a search for May, initially tracked his blue Jeep after a citizen reported seeing it in a Lakeland neighborhood on August 22. An investigator with the group and Lakeland police both went to check on the vehicle that day, and May's family later retrieved the Jeep — but the vehicle is no longer considered part of the active search, leaving investigators without that lead.
We Are The Essentials was founded in 2021 by former law enforcement officers and military veterans who got their start volunteering in the search for Gabby Petito and Brian Laundrie, according to the Osprey Observer. The group has stayed active in the Tampa Bay area since, joining police in December to search for Petro Kuqo, an 87-year-old Largo man with dementia — a case Hoodline covered in a previous search for a missing Largo senior. In June, the nonprofit also conducted ground searches in eastern Hillsborough County for 37-year-old Daniel Herring, who vanished from his Plant City home without his phone, wallet, or vehicle.
How Florida Handles Missing Adults With Mental Health Needs
The Tampa Police Department is investigating May's disappearance and is asking anyone with information to call 813-231-6130, referencing case number 26-492258. Florida law sets no mandatory waiting period before filing a missing person report, which is why May's family was able to report him missing within a day of his last known sighting.
The Florida Department of Law Enforcement also manages the Missing Endangered Persons Information Clearinghouse, a statewide system created by lawmakers in 1996 that coordinates alerts — including Silver, Purple, and Spectrum alerts — for vulnerable or impaired missing adults. Cases involving jailed individuals with mental health or cognitive challenges have drawn scrutiny elsewhere in Florida recently; Hoodline reported earlier this month on a Jacksonville man with autism who disappeared after being released from the Duval County Jail without his family being notified. More than 600,000 people are reported missing across the United States each year, with over 1,200 open missing-person cases active in Florida at any given time, according to NamUs data cited by the Osprey Observer.
For now, May's family is left waiting, checking leads, and hoping he sees their message. As Kieffer put it, they simply want him to know he can come home safely, without fear or shame, while the search for answers continues.
