Raleigh Jeopardy champion faces new arrest for minor exploitation charges

A two-time Jeopardy! winner from Raleigh faces new criminal charges just ten months after his first arrest last year.

Court records show that 44-year-old Philip Joseph DeSena was arrested on Oct. 23 in Wake County. He is charged with 10 counts of second-degree sexual exploitation of a minor. The arrest warrant indicated the charges stemmed from his alleged possession of sexually explicit pictures and videos showing children. DeSena was booked into the Wake County Jail. A judge denied bond during his initial court hearing on Monday.

DeSena lives in Raleigh and works as an engineer. He won two episodes of Jeopardy! in November 2024. Between those two victories, he earned $44,698. He later participated in the show’s Winter 2025 Champions Wildcard tournament in January. His legal troubles began almost a year before this latest arrest.

On Dec. 1, 2025, DeSena was arrested for a second time in a span of less than a year. Prosecutors charged him with two counts of felony secret peeping. Those charges involved the alleged recording of a woman in a bedroom and bathroom. DeSena pleaded guilty to those peeping charges on July 27, 2026. The court sentenced him to 60 months of probation. He was also ordered to complete 100 hours of community service.

As part of that sentence, the court required DeSena to obtain a mental health assessment. Records indicate the court recommended the evaluation be conducted by a psychiatrist or psychologist who specializes in psychosexual treatment. DeSena is now scheduled to appear in court again on Nov. 16 for the new sexual exploitation charges.