Note: the name of the student in the following article has been changed to Jane Doe.
Timothy Whitfield, a 44-year-old resident of Palm Coast hired as a history teacher at Flagler Palm Coast High School last year, was effectively fired two months ago following sheriff’s and district investigations that uncovered grave ethical improprieties but no criminal findings. Whitfield had maintained a relationship with a female student, paid her nearly $6,000 through 127 cash-app transactions, and lied on his job application, hiding his previous firing from the Department of Juvenile Justice over improprieties involving juveniles there.
According to investigative documents obtained by FlaglerLive, the school district became aware of the allegations about Whitfield on Sept. 8. He was placed on paid leave on Sept. 10 and told he was being fired on Sept. 16, without cause, as he was still a probationary employee: he’d been hired only the prior November. Whitfield opted to resign immediately and forego all due process opportunities to review the information in the complaint about him. In an email to FlaglerLive, he wrote: “Write what you want. I have no comment.”
On Aug. 20, Whitfield’s wife had gone to the office of Robert Ouellette, the Flagler school district’s coordinator for professional standards, to meet with him. “Do you know why she wants to meet with me?” Ouellette asked his assistant. “She didn’t specify when I asked. She just said she wants to go over some questions,” the assistant, replied. It isn’t clear if Whitfield’s wife and Ouellette met around that time. Ouellette’s investigative report doesn’t indicate they did so. That 64-page report begins with the Sheriff’s Office’s involvement.
The case there began with an anonymous email tip to the Flagler County Sheriff’s Office on Aug. 27. “We have been hearing Mr. Whitfield a teacher at FPC is having a relationship with a girl [Jane Doe] since February when she was his student. Jane has over 100 cash app payments from him her friends saw for thousands of dollars from Feb 2021 until now. She graduated in June 2021. Mr Whitfield has two phones and he is always messaging students. His number is  and he messages a lot of the female students. There are rumors he left his wife and family and was messing around with Jane. Some other students have said they received money from him through cash app, too. But Jane has hundreds of payments. The students are talking about his relationships with students being ‘weird’. This needs to be looked at and the school board has to handle this behavior. It’s predatory using money and power to solicit .” The Sheriff’s Office surmised the tip may have possibly come from Jane Doe, though documents would later indicate the source was more likely Whitfield’s wife. (In June and July Whitfield and his wife traded petitions for divorce. That case is ongoing.)
The investigation located the alleged victim as a Palm Coast resident who was 19 at the time the investigation began, making her over 18 from the time the alleged relationship with Whitfield had started. An investigator’s meeting with her stepfather revealed she had just moved out of state. When told of the cash Whitfield was said to have passed to Jane Doe, her stepfather said he was aware that a male teacher at FPC had paid for four tires for her car, but that was the extent of any money passing hands that he was aware of. He also thought “it was odd a male teacher would just buy tires for a student out of the kindness of his heart and wondered why the teacher did not discuss it with her parents first.” The stepfather did not describe his stepdaughter in flattering terms, either, calling her manipulative and inappropriate.
In early September Jane Doe’s biological mother told the detective Jane was back in Florida, but she did not have an exact location. Jane’s mother “alluded to the fact that there may have been a sexual encounter between the two parties,” but her daughter would not provide further information, according to that investigation.
The detective then reached Jane Doe by phone. She told the detective that Whitfield had sent money through a cash app but she couldn’t provide a total amount, and that he’d done so four times. She said she’d only seen him “outside of school after she had already graduated from High School,” and described him as a “Sugar Daddy.” She confirmed a sexual encounter took place at his home after graduation, but said she wasn’t interested in continuing it. According to her, he told her “he was not going to give her any more money since she was unwilling to continue this type of relationship with him.” She told the detective that Whitfield himself “stated that he has other girls” willing to have sex with him, according to the investigator’s report. She described the sexual encounter as “consensual in nature, but she felt like [Whitfield] talked her into it,” the report states.
Some of the timeline and the details Jane Doe provided proved to be incorrect–downplaying the amounts that changed hands or indications that she’d been receiving money while still a student.
The investigation was closed and no charges issued. But the case was referred to the district for “potential ethics violations,” according to district documentation. On Sept. 8, David Bossardet, the district’s safety specialist at the time but soon to be an assistant principal at FPC, got a call from the Sheriff’s Office informing him about the just-completed investigation. That started Ouellette’s investigation.
Ouellette met with Whitfield’s wife the next day. In the process of divorce proceedings, Whitfield’s wife had acquired bank records and documentation of the cash app transactions–over 100 of them to Jane Doe. She showed Ouellette copies of bank statements. He analyzed them. There were 127 in all, totaling total of $5,569.25. The payments began on Feb. 17, 2021, when Jane Doe was still a student at the school, and ended on June 20, 2021. Graduation was on June 2. Whitfield’s wife was not aware of payments to other students.
In his application for a teaching job at FPC, Whitfield listed his past employment in descending order, with the Flagler County Sheriff’s Office as what appeared to be the last place he’d worked. It was listed first. He’d been the purchasing manager there for less than a year between 2018 and 2019. He listed as second a brief stint at SMA, or Stewart-Marchman Behavioral, in St. Augustine, as a mental health counselor, and 20 years in the Air Force before that. Only then, as the fourth item, he listed employment with Truecore Behavioral Solutions, the private contractor used by the Department of Juvenile Justice to operate youth facilities. Whitfield listed himself as a warden “responsible for day to day operations and oversight” who “ensured compliance with regulations and guidelines.” His employment there lasted just nine months, from October 2019 to June 2016. As reason for leaving, he wrote: “Company.”
When asked whether he’d ever been investigated for misconduct, he said no–a lie. When asked if he’d ever been fired, he said no–a lie.
It was Whitfield’s wife who showed Ouellette Department of Juvenile Justice documents she had obtained, indicating that Whitfield had been the subject of two internal investigations at DJJ, and was eventually fired for cause.
According to the investigation conducted by DJJ, “On an unknown date and time, [Facility Administrator] Whitfield engaged in a conversation with youth . Youth  told FA Whitfield that he was going to engage in anal sex with his daughter. By FA Whitfield’s own admittance, he told youth- that he should be concerned about his own buttock when he is transferred to another program because he was going to enter the program as [redacted] and exit the program as [redacted].” An interval investigation substantiated that a violation of internal “Rights of Youth” and “Custody of Supervision” DJJ policies took place.
In March 2020, a youth detainee reported that Whitfield hit him, called him names, and threatened to ship him off to another facility where he would be raped, according to internal DJJ documentation. The youth called the Abuse Registry. The call was not accepted for investigation. The DJJ’s investigation states the youth alleged Whitfield “called him a menace to society and that he can’t be around the other kids and also called him a faggot.” A youth witness reported that the incident had happened days prior, in the shower area. Another youth witness “reported that Mr. Whitfield does threaten to hit youth if they hit him.” The DJJ sustained a finding of improper conduct by Whitfield–“threats by staff”–but he was not disciplined or fired at the time. DJJ documents state he was fired on June 26, 2020 “for an unrelated incident and he is not eligible for rehire.”
Flagler Palm Coast High School hired him on Nov. 4, 2020. His application had included a reference from a Flagler County school colleague who’d seen his work as a “permanent substitute” teacher in the district. She described him as “an amazing role model for the students. He is charismatic and has a great sense of humor which the students love. He pushes the students to do their best and uses motivational strategies for struggling students.
On Sept. 16, Ouellette met with Whitfield to review the findings of the investigation and tell him he was being fired. Rather than provide any information about the allegations, Whitfield chose to resign immediately. On Sept. 23, the state Board of Educations Office of Professional Services Practices received the district’s investigative report about Whitfield and assigned its own case number and staffer for review.