2-time ‘Jeopardy!’ winner pleads guilty to felony peeping charges, records show

CURRITUCK COUNTY, N.C. (WBTV/Gray News) - A past “Jeopardy!” winner has pleaded guilty to felony charges in North Carolina.

Philip Joseph “Joey” DeSena, 44, guilty plea this week stems from a December 2025 arrest in which he was charged with two counts of felony secret peeping.

According to an arrest warrant out of Currituck County, DeSena put cameras in a bedroom and bathroom with the intent to capture an image of another person without their consent.

The warrant indicated the alleged crime happened on Oct. 10, 2025, with DeSena turning himself in December. An indictment alleged that the peeping occurred at a rental property.

The 44-year-old was released from the Currituck County jail on Dec. 3, 2025, after posting a $5,000 bond.

Court documents revealed that in exchange for DeSena’s guilty pleas, he was given a 60-month probationary sentence while not being required to register as a sex offender.

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

Between his two wins, DeSena, who has worked as an engineer, totaled $44,698.