2-time ‘Jeopardy!’ winner arrested for 2nd time in less than a year

RALEIGH, N.C. (WBTV/Gray News) — A two-time “Jeopardy!” winner from North Carolina was arrested again, records show.

Court records show 44-year-old Philip Joseph “Joey” DeSena was arrested on Oct. 23 in Wake County.

Charges and arrest details

DeSena was charged with 10 counts of second-degree sexual exploitation of a minor. An arrest warrant indicated the charges stemmed from DeSena’s alleged possession of sexually explicit pictures and videos that showed children.

He was booked into the Wake County Jail and was denied bond during an initial court hearing Monday.

Previous case

DeSena’s latest arrest came almost a year after his first one on Dec. 1, 2025. He was charged with two counts of felony secret peeping following his first arrest. Those charges stemmed from the alleged recording of a female in a bedroom and bathroom.

DeSena pleaded guilty to the peeping charges on July 27, 2026. He was subsequently sentenced 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.

Records showed the court recommended the assessment or evaluation be completed by a psychiatrist or psychologist who specializes in psychosexual treatment.

He is scheduled to be back in court on the new sexual exploitation charges on Nov. 16.

‘Jeopardy!’ background

DeSena, who lives in Raleigh, won two episodes of “Jeopardy!” in November 2024, and participated in the show’s “Winter 2025 Champions Wildcard” tournament in January.

Between his two wins, the engineer raked in $44,698.