Detectives from the Polk County Sheriff’s Office arrested a Winter Haven High School teacher on Thursday, July 23, 2026, after an investigation revealed that he had sexually battered a 15-year-old student numerous times whom he met at Winter Haven High in his capacity as a teacher. Cutshaw is also the boy’s tennis coach there.

55-year old Otis Cutshaw of Winter Haven was transported to the Sheriff’s Processing Center and charged with: 5 counts of sexual battery by custodial figure (FL), 5 counts of travelling to meet a minor (F2), 5 counts of unlawful use of a two-way communication device (F3), 7 counts of transmission of harmful material to a minor (F3), 8 counts of possession of obscene material depicting a minor (M2), use of a device to solicit sexual conduct with a minor (F3), child pornography (F3), offenses against students by authority figures (F2), lewd molestation (F2), and tampering with physical evidence (FL).

The PCSO investigation began on Wednesday, July 22, 2026 after it was discovered that the victim was in an inappropriate relationship with the 55-year-old suspect. 

Detectives made contact with the victim who admitted that she had been in a sexual relationship with Cutshaw since school ended in May 2026 and that they communicated through messaging apps like GroupMe. According to the victim, the encounters occurred frequently at the beginning of summer and then daily during this past week.

When detectives retrieved her phone, their messages appeared to have been deleted, but they were able to find substantial message history through forensic analysis. Detectives found numerous pictures, videos, and messages all predominately sexual in nature including photographs and videos of Cutshaw with his penis exposed or while masturbating that he had sent to the victim.

During a phone call between the victim and Cutshaw, he told her that he deleted their chat history and that he needed to know what she had told law enforcement so that they could “match their stories.”

While speaking to detectives, Cutshaw admitted to traveling to the victim’s residence and engaging in oral sex and penile-vaginal intercourse without a condom on approximately five occasions while her parents were away. He also admitted to exchanging nude photos and videos, providing the victim with gifts, and deleting their chat history because he knew law enforcement was coming to his house. Cutshaw also stated that despite the circumstances, he remains optimistic that he will eventually be able to marry the 15-year-old victim. Cutshaw is married and has two kids of his own.

“We are disgusted to hear that someone entrusted with educating and protecting children has been arrested for such unacceptable behavior,” said Fred Heid, superintendent of Polk County Public Schools. “We are terminating his employment, and he will have no further involvement with our students. The school district will continue to cooperate fully with the Polk County Sheriff’s Office investigation, and we appreciate deputies moving so quickly to address this situation.”

Click here to hear Sheriff Judd’s comments on this arrest.