Philip Joseph “Joey” DeSena, 43, a 2014 past winner of “Jeopardy!” from Raleigh, North Carolina, was apprehended on December 1, 2025, and charged with two felony counts of secret peeping. DeSena, a development engineer, is alleged to have covertly installed cameras in a bathroom and bedroom.
The Currituck County Sheriff’s Office arrest warrant indicates the incident occurred on October 10, 2025, but the warrant was not issued until November 26. Court documents reveal DeSena allegedly illicitly set up a camera in a bathroom to secretly capture images of an individual. DeSena surrendered to Wake County authorities and was released from jail on December 3 after posting a $5,000 bond. Court orders mandated no contact with the victim and required DeSena to give fingerprints and a DNA sample.
A hearing to determine probable cause was arranged for December 10 at Currituck County Court. As of December 14, no additional court developments have been disclosed. Each felony charge he faces could lead to a sentence ranging from three to 24 months in jail. DeSena has no other significant prior criminal history.
DeSena gained prominence when he participated in “Jeopardy!” in November 2024, securing wins in two consecutive games and earning a total of $44,698. His first victory on November 11, 2024, netted him $17,487. He won again the following day, but lost his third game. His first episode stirred controversy when both his competitors ended with $1 after risking everything in Final Jeopardy, causing a tie for second and third place. DeSena wore his father’s Navy pin as a personal homage during the competition and shared on Reddit: “This was my little way of paying tribute to him on the Alex Trebek Stage. I made it, Dad.”
In January 2025, DeSena returned to engage in the Champions Wildcard Tournament, aiming for a slot in the 2025 Tournament of Champions. His quarterfinal performance was among the tournament’s strongest, answering 20 out of 22 questions correctly and successfully completing two Daily Doubles. However, he was defeated in the semifinals by Drew Goins and Jen Feldman.
While on the show, DeSena interacted with fans on the “Jeopardy!” Reddit forum. In one post, he shared that he wrote “Lorelai” during a Final Jeopardy round as a message to his four-month-old daughter, hoping she would see it in the future and be pleased. He also revealed that host Ken Jennings admitted the Final Jeopardy question was tough and that he did not know the answer, which DeSena found comforting after failing to answer correctly.
DeSena first applied to appear on “Jeopardy!” in 2010 and waited over a decade before finally competing in November 2024. His two victories were recorded during the same morning session. Prior to his television appearance, DeSena was known in the retro-gaming community, working on projects such as 16 Bit Gems, Apollo Z Hack, and The Video Game Years. From 2009 to 2015, he managed a YouTube channel named ClanOfTheGrayWolf under the pseudonym “Roo.”
This is not the first instance of a “Jeopardy!” contestant facing serious legal charges. In March 2025, former champion Winston Nguyen was sentenced to seven years in prison for impersonating a teenager on Snapchat to solicit explicit images and videos from minors. In 2014, Paul Curry, a former show participant, was found guilty in the 1994 nicotine-poisoning death of his wife.
