Raleigh man arrested again after Jeopardy! wins

Philip Joseph DeSena was arrested in Wake County on Oct. 23. He is 44 years old and lives in Raleigh. The arrest marks his second custody incident in less than a year.

Court records show officers charged him with 10 counts of second-degree sexual exploitation of a minor. The arrest warrant stated the charges resulted from his alleged possession of sexually explicit pictures and videos showing children. He was booked into the Wake County Jail. A judge denied his request for bond during an initial hearing on Monday.

This follows a previous case that began on Dec. 1, 2025. DeSena was then charged with two counts of felony secret peeping. Those charges stemmed from allegations that he recorded a woman in a bedroom and a bathroom. He pleaded guilty to those charges on July 27, 2026. The court sentenced him to 60 months of probation. He also received 100 hours of community service. The court ordered a mental health assessment by a specialist in psychosexual treatment.

DeSena gained public attention as a contestant on the television show Jeopardy!. He won two episodes in November 2024. He later entered the Winter 2025 Champions Wildcard tournament in January. He earned $44,698 between his two wins on the show.

He is scheduled to return to court on Nov. 16 to address the new sexual exploitation charges.