Raleigh Engineer Pleads Guilty to Peeping, Faces New Charges

A 44-year-old Raleigh man who appeared on the game show Jeopardy! twice last year faces ten new criminal counts in North Carolina. Court records indicate Philip Joseph DeSena was arrested in Wake County on October 23. The charges allege he possessed sexually explicit images and videos of children. He was charged with 10 counts of second-degree sexual exploitation of a minor.

DeSena was booked into the Wake County Jail following his arrest. A judge denied bond during his initial hearing on Monday. He will return to court on November 16 to address the new charges. An arrest warrant noted that the case stems from the alleged possession of digital media showing minors.

This is DeSena’s second arrest in less than a year. He was previously charged with two counts of felony secret peeping in December 2025. Those earlier charges involved the alleged recording of a woman in a bedroom and a bathroom. He pleaded guilty to those offenses on July 27, 2026. The court sentenced him to 60 months of probation and ordered 100 hours of community service.

The judge also required DeSena to complete a mental health assessment. Records show the court recommended that this evaluation be conducted by a psychiatrist or psychologist who specializes in psychosexual treatment. DeSena lives in Raleigh and works as an engineer. He gained public attention after winning two episodes of Jeopardy! in November 2024. He also participated in the show's Winter 2025 Champions Wildcard tournament in January. Between his two wins, he earned a total of $44,698.