Raleigh Jeopardy! Winner Charged With Sexual Exploitation of Minors

Philip Joseph DeSena, a 44-year-old Raleigh resident and two-time Jeopardy! champion, was arrested on Oct. 23 in Wake County. He now faces 10 counts of second-degree sexual exploitation of a minor. The charges are related to the alleged possession of sexually explicit photos and videos depicting children.

DeSena was booked into the Wake County Jail on Thursday. During his initial court hearing on Monday, the judge denied bond. He is scheduled to return to court on Nov. 16 to address the new charges. His arrest marks his second detention in less than a year.

DeSena was first arrested on Dec. 1, 2025. At that time, he was charged with two counts of felony secret peeping. Those charges stemmed from the alleged recording of a woman in a bedroom and bathroom. On July 27, 2026, DeSena pleaded guilty to the peeping charges. He received a sentence of 60 months of probation. The court also ordered him to complete 100 hours of community service and obtain a mental health assessment.

Court records indicate the assessment must be performed 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 earned a total of $44,698 from those two victories. He also competed in the show’s Winter 2025 Champions Wildcard tournament in January.