Philip Joseph ‘Joey’ DeSena, a former Jeopardy! champion with two consecutive wins to his name, now finds himself in a much less celebratory spotlight. The 42-year-old was recently arrested in Maple, North Carolina, facing accusations that cast a shadow on his previous achievements.

The Currituck County Sheriff’s Office apprehended DeSena last Monday, following allegations that he engaged in illicit surveillance activities. According to court documents, DeSena allegedly installed a camera in a bathroom on October 10, intending to record someone without their knowledge or consent. This unsettling development, first reported by the New York Post, has brought serious legal repercussions for the once-celebrated contestant.

DeSena is charged with two counts of felony secret peeping, a grave accusation that has led to his release on a $5,000 bail. As he awaits his first court appearance, scheduled for this Wednesday, the charges highlight a stark contrast to his previous public image as a software developer from Raleigh.

The allegations describe DeSena’s actions as ‘unlawful, willful, and felonious,’ accusing him of using a device capable of creating photographic images to invade another’s privacy. The accusations have raised significant concerns over privacy and consent, painting a troubling picture of a man once celebrated for his quick wits on television.

The software developer, who hails from the state capital of Raleigh, stands accused of having ‘unlawfully, willfully, and feloniously’ put in ‘any device that can be used to create photographic image, namely a camera placed in the bathroom, with the intent to capture the image of another without their consent.’ 

The Daily Mail has reached out to DeSena’s attorney for comment. 

Jeopardy! contestant Philip Joseph ‘Joey’ DeSena, who won two nights in a row last year, has been arrested and accused by the authorities of being a peeping tom

DeSena made his inaugural Jeopardy! appearance on November 11, 2024, won that night and came back and won again November 12. 

Although he lost on November 13, cutting off his winning streak, he returned this January for the Champions Wildcard tournament and made the semifinals.

This March a previously Jeopardy! winner, New York City math teacher Winston Nguyen, was sentenced to seven years in prison for catfishing his students into sending him lewd images.

Nguyen was given a second chance in 2020 to teach at the prestigious Saint Ann’s private school in Brooklyn after he was convicted on fraud charges.

But just four years later, the math teacher was arrested again – sending the prep school spiraling into a PR crisis.

Nguyen was hired as an administrative aide in 2020, just one year after he was convicted for fraud for stealing more than $300,000 from an elderly couple while employed as their home health support.

Maureen ‘Mo’ Yusuf-Morales, the Head of the Upper Middle School at Saint Ann’s and an experienced DEI trainer, had pushed for him to be given a chance, despite his past crimes.

He had declared to the administrator that he was a convicted felon, and according to the New York Times at least one of the school leaders vehemently opposed the decision to hire him regardless.

And yet, he was given a second shot, climbing his way through the ranks to ultimately earn a math teaching gig by 2021 at a school known for unorthodox teaching methods. He also taught a seminar called ‘Crime and Punishment.’ 

DeSena made his inaugural Jeopardy! appearance on November 11, 2024, won that night and came back and won again November 12

Parents were not alerted to Nguyen’s criminal record, but students quickly discovered news articles about his initial crime on the internet.

When parents expressed concerns to the school, they were dismissed. In October 2021, head of school Vince Tompkins sent an email which assured families ‘as with any teacher we hire, we are confident in Winston’s ability and fitness to educate and care for our students.’

Multiple parents and witnesses later reported they feared they’d be branded ‘racist’ or ‘not progressive enough if they raised a substantive concern about a person of color.’

Then in 2022, students at both Saint Ann’s and other private schools within Brooklyn began reporting that they were receiving solicitations via Snapchat for inappropriate photos and videos.

Some of these students were as young as 13. The District Attorney’s office alerted Saint Ann’s in February 2024 that an investigation was taking place into the anonymous account. Parents were not notified.

Nguyen, who competed in and won Jeopardy! in 2014, was ultimately arrested in June 2024 and charged with a litany of offences.

Yusuf-Morales, who allegedly pushed the hardest to hire Nguyen, left Saint Ann’s and took a job at a charter school in Brooklyn.