Raleigh Engineer: Jeopardy! Winner Faces Child Exploitation Counts
Philip DeSena, who won two Jeopardy! episodes in 2024, was denied bond Monday after his second arrest in under a year.
By Lina Lewis ·
Philip Joseph DeSena, a Raleigh engineer who won two Jeopardy! episodes, was booked into the Wake County Jail on Oct. 23 on 10 counts of second-degree sexual exploitation of a minor. An arrest warrant states the counts stem from allegedly possessing explicit pictures and videos depicting children. A judge denied bond at his initial hearing Monday.
DeSena, 44, won back-to-back games in November 2024, earning $44,698 across the two victories. He returned to the show for the Winter 2025 Champions Wildcard tournament in January 2026.
His first arrest came Dec. 1, 2025, when he was charged with two counts of felony secret peeping for allegedly recording a woman in a bedroom and bathroom. He pleaded guilty to those counts on July 27, 2026 and received 60 months of probation, 100 hours of community service and a requirement to complete a mental health assessment. The court recommended that assessment be conducted by a psychiatrist or psychologist specializing in psychosexual treatment.
Court records list his next appearance on the exploitation charges for Nov. 16.
