Raleigh Jeopardy! Winner Joins Wake County Jail Roster Again

Raleigh, N.C. resident Philip Joseph "Joey" DeSena is back in the Wake County Jail following his second arrest in under a year. The 44-year-old two-time Jeopardy! winner was taken into custody on Oct. 23.

Court records show DeSena was charged with 10 counts of second-degree sexual exploitation of a minor. An arrest warrant stated the charges arose from his alleged possession of sexually explicit pictures and videos featuring children. He was denied bond during an initial hearing on Monday.

DeSena's legal troubles began in late 2025. On Dec. 1, 2025, he was arrested and charged with two counts of felony secret peeping. Those charges stemmed from the alleged recording of 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 was also ordered to complete 100 hours of community service and obtain a mental health assessment from a specialist in psychosexual treatment.

The engineer won two episodes of Jeopardy! in November 2024. He earned a total of $44,698 from those victories. He later participated in the show's Winter 2025 Champions Wildcard tournament in January.

DeSena is scheduled to appear in court on Nov. 16 to address the new sexual exploitation charges.