Raleigh engineer wins Jeopardy, faces new arrest

A Raleigh engineer who won two episodes of Jeopardy! in 2024 was arrested again in North Carolina.

Court records show 44-year-old Philip Joseph DeSena was taken into custody on Oct. 23 in Wake County. He faces 10 counts of second-degree sexual exploitation of a minor. The arrest warrant states the charges stem from his alleged possession of sexually explicit pictures and videos showing children.

DeSena was booked into the Wake County Jail. He was denied bond during an initial court hearing on Monday, Oct. 26. He is scheduled to return to court on Nov. 16 for the new sexual exploitation charges. The previous case ended in July when he pleaded guilty to two counts of felony secret peeping. Those charges came from his first arrest on Dec. 1, 2025, which involved allegedly recording a female in a bedroom and bathroom.

The court sentenced DeSena to 60 months of probation on July 27, 2026. He also received 100 hours of community service and a mental health evaluation. Records indicate the court recommended the assessment be done by a psychiatrist or psychologist specializing in psychosexual treatment.

DeSena lives in Raleigh and is an engineer. He won two Jeopardy! episodes in November 2024 and earned a total of $44,698. He also entered the show’s Winter 2025 Champions Wildcard tournament in January.