A two-time “Jeopardy!” winner from Raleigh, North Carolina, is back in jail. Philip Joseph “Joey” DeSena, 44, was arrested on 10 felony counts of second-degree sexual exploitation of a minor, court records show.
Police arrested him Friday, Oct. 23, in Wake County. He was booked into the Wake County Detention Center. After his first court appearance Monday, Oct. 26, a judge denied him bond.
The arrest warrants say DeSena had and copied 10 digital files showing the sexual exploitation of children. Investigators estimated the children in the files were between 7 and 15 years old. The warrants list Nov. 19, 2025, as the date of the alleged offenses. These are allegations. DeSena has not been convicted in this case.
This is not his first run-in with the law. In October 2025, at a rental property in Corolla, North Carolina, police say he secretly put cameras in a bedroom and a bathroom to record a person without their consent. He was arrested in December 2025 and charged with two felony counts of secret peeping.
He pleaded guilty to both on July 27, 2026. The sentence was 60 months of probation. He was also ordered to do 100 hours of community service and to get a mental health assessment. Court records recommended a psychiatrist or psychologist who specializes in psychosexual treatment. Under the plea deal, he was not required to register as a sex offender.
The new charges came while he was still on probation for that case. He is due back in court on the new charges Nov. 16.
Many people knew DeSena from TV. He won two games in a row on “Jeopardy!” in November 2024 and took home $44,698. He lost his third game. He later returned for the Champions Wildcard tournament and made it to the semifinals before being knocked out.
The case is being handled in Raleigh, the seat of Wake County. DeSena is being held at the detention center at 3301 Hammond Road.
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