A former “Jeopardy” winner and math teacher at a posh Brooklyn private school pleaded guilty Monday in exchange for a seven-year sentence to charges he posed as a teen and enticed students to send him nudes on social media.

The elite St. Ann’s School in. Brooklyn Heights first hired Winston Nguyen, 38, in August 2020 to fill a “classroom assistant” role handling COVID-related remote learning issues, despite his conviction the prior year on fraud charges. He started teaching math full time in 2021.

His creepy catfishing scheme began the next year, and from October 2022 to May 2024, he used Snapchat to chat up at least five girls and one boy in at least 11 separate incidents. The victims were students at Saint Ann’s School, Poly Prep Country Day School, Berkeley Carroll School and Packer Collegiate Institute.

Nguyen pleaded guilty before Brooklyn Supreme Court Justice Philip Tisne to a single count of use of a child in a sexual performance as a sexually motivated felony and five counts of endangering the welfare of a child. As part of his plea deal, he must also serve 10 years on supervised release and register as a sex offender.

Winston Nguyen (left), a former math teacher at Saint Ann's School, pleads guilty to child sex offenses at Brooklyn Supreme Court with his defense lawyer Frank Rothman on Monday.
Michael Nagle/Pool

Winston Nguyen (left), a former math teacher at Saint Ann’s School, pleads guilty to child sex offenses at Brooklyn Supreme Court with his defense lawyer Frank Rothman on Monday. (Photograph by Michael Nagle/Pool)

He was cuffed after his guilty plea and ordered held without bail, and is slated to be sentenced March 17.

“There was really never an issue about whether or not he had to plea guilty,” said his lawyer, Franklin Rothman said. “There’s very little defense one can proffer when you have images on your phone … It was never an issue of him denying responsibility.”

Rothman said he expects Nguyen will apologize to his victims and to the people who trusted him when he’s sentenced in two weeks.

Nguyen used the account name “hunterkristoff” to send a video depicting a nude boy masturbating to a 14-year-old, then asked the teen to send nude or sexual images. He communicated with four more victims, aged 13 to 15, from that account.

Nguyen communicated with a sixth victim, age 15, from an account named “haircutbongos,” and in May 2024, the teen performed a sex act on video for Nguyen in exchange for money, prosecutors said.

Several students at St. Ann’s reported falling prey to catfishing schemes starting in February 2024, and the school contacted authorities, but school leadership didn’t learn of Nguyen’s involvement until his arrest in June, according to an investigative report commissioned by the school.

Investigators tied the two accounts to IP addresses connected to Nguyen’s Harlem home, and the Brooklyn D.A.’s office charged him on a criminal complaint in June.

Nguyen, who won $10,000 on “Jeopardy” in 2014, was arrested three years later on charges he swindled a couple in their 90s out of $335,000 by writing checks in their names and using their accounts and credit cards while working as a home health aide.

One of the victims, who was blind, blasted Nguyen as a “terrible person” in a 2017 interview with the Daily News. He pleaded guilty to grand larceny and other charges in 2019, and served four months in jail.

The then-head of the upper middle school at St. Ann’s, Maureen Yusuf-Morales, a longtime friend of Nguyen, got him a job interview in August 2020, vouching for him and assuring the then-dean of faculty Melissa Kantor that he had reformed, according to the 39-page investigative report.

The school hired him before his background check was completed, and even after they got the results, administrators kept him on staff and didn’t share his criminal record with students’ families and other teachers, the report found.

When students found out on their own by looking him up on the internet and confronting him in class in October 2021, he told them he “committed his crimes because he felt the need to buy things for his friends in order to be liked by them,” according to the report.

A number of students upset with the revelations were “shamed” by Yusuf-Morales for not supporting restorative justice or for spreading rumors, according to the report.

“Today’s plea holds this defendant responsible for his disturbing and predatory conduct while sparing young and vulnerable victims from ever having to testify about their traumatic experiences,” Brooklyn D.A. Eric Gonzalez said Monday. “This kind of exploitation of children, made even more distressing by the fact that the defendant was a trusted school figure, will never be tolerated in Brooklyn and we will continue to expose and root it out.

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