Raleigh engineer who won $44,698 on Jeopardy! faces 10 new charges

A Raleigh engineer who appeared on Jeopardy! in 2024 was arrested in Wake County on Oct. 23. Court records identify the suspect as Philip Joseph DeSena, 44. He now faces 10 counts of second-degree sexual exploitation of a minor.

The arrest warrant states that the charges stem from DeSena’s alleged possession of sexually explicit pictures and videos showing children. Police booked him into the Wake County Jail following the arrest. A judge denied bond during his initial court hearing on Monday.

This is DeSena’s second arrest in less than a year. On Dec. 1, 2025, he was charged with two counts of felony secret peeping. That case involved the alleged recording of a woman in a bedroom and a bathroom. DeSena pleaded guilty to those 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 and obtain a mental health assessment.

Court records indicate the assessment should be performed by a psychiatrist or psychologist who specializes in psychosexual treatment. DeSena is scheduled to appear back in court on Nov. 16 to address the new sexual exploitation charges.

DeSena lives in Raleigh and won two episodes of Jeopardy! in November 2024. He later participated in the show’s Winter 2025 Champions Wildcard tournament in January. His two wins earned him $44,698.