Raleigh 'Jeopardy!' winner faces new charges

Philip Joseph “Joey” DeSena, a Raleigh resident and two-time “Jeopardy!” champion, was arrested in Wake County on Oct. 23. Court records indicate he is now charged with 10 counts of second-degree sexual exploitation of a minor. An arrest warrant stated the charges result from his alleged possession of sexually explicit pictures and videos depicting children.

DeSena, 44, was booked into the Wake County Jail. He was denied bond during an initial court hearing held on Monday. This arrest follows a previous legal proceeding that began in December of last year.

DeSena was first arrested on Dec. 1, 2025, and charged with two counts of felony secret peeping. Those charges stemmed from allegations that he recorded a female in a bedroom and a bathroom. On July 27, 2026, he pleaded guilty to both counts. The court sentenced him to 60 months of probation. He was also ordered to complete 100 hours of community service and to obtain a mental health assessment or evaluation.

Court records show the assessment must be completed by a psychiatrist or psychologist specializing in psychosexual treatment. DeSena currently resides in Raleigh. He won two episodes of the game show “Jeopardy!” in November 2024. He also participated in the show’s “Winter 2025 Champions Wildcard” tournament in January. Between his two wins, the engineer earned a total of $44,698.

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