Math Teacher at Elite Brooklyn School Arrested in Sexualized Image Probe

Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty
Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty

A math teacher at an elite Brooklyn private school has been arrested during an investigation into sexualized images shared through social media—leaving high-powered parents scrambling for answers on what happened just days before graduation.

Cops busted Winston Nguyen—a onetime Jeopardy! contestant who in 2017 was charged with siphoning a large sum from an elderly couple to bankroll a lavish lifestyle—at Saint Ann’s School in celebrity hotspot Brooklyn Heights last Thursday in front of a crowd of students. He was released Saturday.

Nguyen wasn’t charged but remains a suspect in an ongoing investigation by the Brooklyn District Attorney’s Office, which confirmed his arrest to The Daily Beast.

When reached by a Daily Beast reporter, Nguyen laughed and said New York magazine had “a 12-hour head start” on this reporting and referred us to his lawyer.

A spokeswoman for Saint Ann’s—where tuition can run up to $60,000 a year—said the DA’s office “confirmed for us that Winston is a suspect in an ongoing investigation related to the dissemination of intimate images via social media.”

“Upon his arrest on Thursday,” she added, “he was immediately placed on leave by the school and he remains on leave.”

On June 6, Saint Ann’s Head of School Kenyatte Reid sent an email to parents announcing Nguyen’s arrest but conceding he didn’t know “the specific charges.”

“I was informed this evening by the Assistant District Attorney that his arrest is in relation to an investigation that dates back to January 2024,” Reid wrote.

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Days later, Reid delivered another email update, saying Nguyen was a suspect in an ongoing investigation related to “inappropriate sexualized images” and that he’s barred from contacting anyone in the school community and from visiting the school.

Reid added that the DA’s office asked any “families with information related to Winston’s conduct or any suspicious activity on Snapchat or any social media” to come forward. “This incident is very disturbing to all of us,” Reid said. “We pride ourselves on our amazing faculty and a learning environment rooted in trust.”

The renowned school boasts star-studded alumni including actresses Lena Dunham and Jennifer Connelly, artist Jean-Michel Basquiat (who attended for a year and did not graduate), as well as Levon and Maya Hawke, the children of Hollywood stars Ethan Hawke and Uma Thurman. Among the school’s parents are TV personalities, top-selling authors, lawyers, and investors.

The artsy school, which eschews giving grades, is so popular that in 2016, actor Matt Damon reportedly couldn’t snag spots for his own kids.

But it’s also faced controversies over the years, including an internal probe in 2019 that uncovered multiple instances of staff—such as founding headmaster Stanley Bosworth—engaging in sexual misconduct with students from the 1970s through the 1990s.

Nguyen was hired in 2020, the Saint Ann’s spokeswoman said, and his last position was as a middle- and high-school math teacher. Asked whether administrators were aware of his criminal history, the representative said the school conducts comprehensive background checks that include criminal records when hiring employees.

“A nonviolent criminal record may not preclude employment,” she added, “The school gives a careful and discerning assessment of a job candidate’s potential fit with the school.”

“We are fully cooperating with law enforcement in their efforts, and right now we’re focused on helping our students process this news.”

A memo sent by Saint Ann’s School in Brooklyn to parents and members of the community.

A memo sent by Saint Ann’s School in Brooklyn to parents and members of the community.


Nguyen’s lawyer, Frank Rothman, said the DA’s office has declined to immediately prosecute the case pending further investigation.

“That’s where things are at right now,” Rothman told The Daily Beast. “They are investigating, and they will make a decision in the near future as to what, if anything, to charge him with.”

“I don’t think this is something that’s just going to be a non-issue,” Rothman added, “There’s going to be an issue. The question is, how big and when?”

On Thursday, parents were questioning how Nguyen could land a job at the prestigious Saint Ann’s despite his scam of the elderly couple making tabloid fodder—as well as his lawsuit against the city’s Department of Correction Commissioner over Rikers Island allegedly censoring newspapers and failing to provide socks and underwear.

“What in the actual hell? How did we get here?” one Saint Ann’s parent told The Daily Beast. “What does the vetting process look like? What does the background process look like?

“He had not been a teacher before,” they added. “He was smart and went to great schools—but still if you are about to hire an ex-Rikers inmate accused of a serious crime, I think we have to go past a basic interview and résumé.

“The idea that this was a person that was close to my’s terrifying.”

The parent said they learned that male students were getting friend requests from social media accounts that were later linked to Nguyen.

“I see him as a manipulator and a con man,” they said. “He conned an elderly couple and he came in as a Covid hire under a different school administration.”

A summer 2021 issue of the school’s Saint Ann’s Times noted that Nguyen “joined us this year as Special Assistant for Covid-Related Projects” and would “stay on as Special Assistant to the Administrative Team” and “also teach a math class.”

Meanwhile, a directory of faculty for the 2021-2022 school year listed Nguyen as a graduate of Columbia University and private tutor in math, Latin, English, and standardized testing. It also chronicled his past positions as a diversity consultant at other city schools.

This isn’t the first time Nguyen has been in the crosshairs of the law.

In August 2017, while working as a home health aide, Nguyen was arrested for swindling more than $300,000 from a 96-year-old blind man and his 92-year-old wife in Manhattan. The arrest came three years after he appeared on Jeopardy.

Prosecutors said that in 2015, six years after he was hired to help the elderly couple, Nguyen used the couple’s credit cards and bank account to fund trips to Florida and tickets to the ballet and Broadway shows.

As part of the scheme, Nguyen even went as far as forging the couple’s bank statements and impersonating their son in conversations with their condo board, the Manhattan District Attorney’s Office said at the time.

Rothman told The Daily Beast that Nguyen pleaded guilty, served jail time and probation, and was ordered to pay restitution.

“We felt so sad for this couple,” one worker at the couple’s Upper East Side digs told the New York Daily News in 2017. “They trusted him so much. He betrayed them. He was posing as a big shot, as a millionaire.”

While awaiting trial at Rikers, Nguyen frequently complained about the notorious jail’s conditions—twice calling into a radio show to relay his gripes to then-Mayor De Blasio.

According to a letter Nguyen wrote to the city in June 2019, he was incarcerated at Rikers from January through May of that year. In his missive, he proposed changes to the inmate rulebook related to “sexually explicit material” and contact between inmates. “Not all physical contact is rape,” he wrote. “Not all physical contact leads to rape.”

In November 2019, a judge ultimately tossed Nguyen’s lawsuit over Rikers failing to provide basic necessities because he was no longer an inmate. (That same month, the scammer took a plea deal and was sentenced to time served, the New York Post reported)

Nguyen fumed to the Post that he’d appeal the judge’s ruling and perhaps pursue a class-action suit against the city.

He complained that while incarcerated, he didn’t have the resources to file a petition that wouldn’t be dismissed.

“Underwear is not headline news,” Nguyen said. “The more we let them get away with the small things, the easier it is for them to get away with bigger things.”

Read more at The Daily Beast.

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