More Accusations Of Sexual Assault Made Against Riverhead Principal During His Time At Eastport-South Manor Schools

icon 1 Photo

author on May 31, 2019

A former student in Eastport-South Manor schools more than 15 years ago has leveled a second accusation against Charles Regan, the Riverhead High School principal and Quogue resident who was accused last month of inappropriate behavior with an 18-year-old student there, saying he sexually assaulted her and committed statutory rape when she was a minor student and he was her basketball coach.

The former student plans to sue the school district for $20 million, attorney John Ray said in a press release on Friday. He also represents the Riverhead accuser, Anastasia Stapon.

In the notice of claim, served on Eastport-South Manor School District officials on May 16, the woman claimed that, beginning at 13 years old, she was sexually groomed by Mr. Regan over a five-year period while she attended Dayton Avenue School and, later, Eastport High School. She said she was sent sexually charged electronic messages, and had sexual contact, including intercourse, with him on several occasions, beginning when she was 16. The incidents left her “severely mentally and psychologically damaged,” according to the document.

It also stated that school district administrators and employees knew of the affair between Mr. Regan and the student and failed to appropriately address the problem.

At the request of the woman, through her attorney, The Press has agreed not to identify her by name.

The woman, now in her mid-30s, said she first encountered Mr. Regan when he became her basketball coach. From that point up until her graduation from high school, Mr. Regan actively pursued sexual relations with her, she charges.

He acted as her counselor and frequently spent time with her in and out of school.

“She has been destroyed. Her coach, who had been her mentor, her hero, is in fact just a pervert who used his power over her to ensnare her in his dirty sexual traps,” the document states. “She was especially defenseless, a sitting target for a predator.”

Mr. Regan was hired in October 1997 and resigned in June 2006 to become assistant principal at Riverhead High School. The notice of claim describes the former student’s allegations against Mr. Regan and district administrators and employees from 1997 through 2002—the period in which the allegations were made. Mr. Regan, now 48, was a special education teacher and basketball coach in the South Manor School District at the time, prior to the district’s complete merger with the Eastport School District.

The notice of claim describes their first sexual encounter, saying Mr. Regan took the student on a date when she was 16, provided her with alcoholic beverages and later made her perform oral sex. Her late return home that night prompted her mother to report the encounter to Eastport district administration.

An investigation into their relationship by Eastport and South Manor district administrators fell short when Mr. Regan and the then-student gave a false story as to why she came home late, according to the notice. Documents stated that her mother did not believe the story and later sent copies of electronic sexual messages between the two to administrators, who did not take any action.

“He used exactly the same grooming techniques upon her that he’s used on other victims as well, including Anastasia. And, of course, very effectively—they worked,” her Miller Place-based attorney, Mr. Ray, said in an earlier interview. He added that he knows of one other alleged victim from Mr. Regan’s time at Eastport-South Manor but said that he is not currently representing that individual.

Anastasia Stapon, 18, a senior at Riverhead High School, came forward publicly in early May accusing Mr. Regan of forcibly kissing her in his office a week prior and said that he had sexually groomed her for months before that. She said at a press conference that she plans to sue him, the Riverhead School District and its board members for $10 million.

Mr. Ray said that the Suffolk County district attorney's office agreed to investigate Anastasia's case.

On Friday, Mr. Ray added, “This fellow is probably the most evil sexual predator I’ve encountered in my 36 years and I’ve encountered many of them. He’s got to be the worst, the most insidious of them all.”

He said that he has not received any response from the Eastport-South Manor district after submitting the notice of claim. A complaint will soon be filed in court to begin legal proceedings, he added.

Eastport-South Manor district administrators did not return requests for comment.

After the district denied a Freedom of Information Law request for the notice of claim—a precursor to a lawsuit—The Press obtained a copy of the document. The district had denied both a FOIL request for the notice of claim and an appeal for a redacted copy, citing its exemption of disclosure because it is an educational record, and that disclosure would constitute “an unwarranted invasion of personal privacy.”

You May Also Like:

Plungers Take Frosty Dip for Heart of the Hamptons

Over 100 people turned out for Heart of the Hamptons’ annual Polar Bear Plunge, where ... 15 Dec 2025 by Staff Writer

Community News, December 18

HOLIDAY HAPPENINGS Holiday Movie Marathon The Hampton Bays Public Library, 52 Ponquogue Avenue in Hampton ... by Staff Writer

Southampton History Museum To Host 'Hearthside Cheer' Event

The Southampton History Museum will welcome the community to Rogers Mansion on Saturday, December 20 for “Hearthside Cheer,” an annual holiday gathering that blends historic tradition, music, and culinary heritage within the 19th-century home. The event will take place from 5 to 8 p.m. and invites guests to join museum staff, board members, and neighbors for an evening of seasonal warmth. The mansion will be adorned with vintage holiday décor, including handmade ornaments from the 1960s through the 1980s, each reflecting stories of craft and celebration. Traditional musicians Maria Fairchild on banjo and Adam Becherer on fiddle will perform historic ... by Staff Writer

Antique Holiday Toy Exhibit Opens in Westhampton Beach

The Westhampton Beach Historical Society is inviting the community to its annual Antique Holiday Toy Exhibit, running Saturdays and Sundays from noon to 3 p.m. through Janury 4. The society’s museum is at 101 Mill Road in Westhampton Beach. The exhibit features more than 100 years of holiday toys, including games, dolls, trains and gadgets. Visitors can explore the evolution of play and experience a dazzling display of toys that shaped holidays past. For more information, visit whbhistorical.org. by Staff Writer

School News, December 18, Southampton Town

Hampton Bays Students Inducted Into Math, Science Honor Societies Hampton Bays High School recently inducted ... by Staff Writer

Community Cooperative Project Plants Beach Grass

Southampton Town’s ongoing effort to restore and protect the shoreline at Foster Memorial Long Beach ... by Staff Writer

Daryn Elizabeth Sidor of East Quogue Dies December 13

Daryn Elizabeth Sidor of East Quogue died peacefully on December 13, after a courageous battle ... by Staff Writer

Southampton Elks Hold Successful Food Drive

The Southampton Elks Lodge 1574 held a community food drive to support Heart of the ... by Staff Writer

CMEE To Host Family New Year's Eve Event

The Children’s Museum of the East End in Bridgehampton will ring in 2026 with a daytime New Year’s Eve celebration designed especially for young families. The museum will host its annual New Year’s Eve Bash on Wednesday, December 31, from 10 a.m. to noon. During the event, children will make noisemakers, share resolutions for the coming year and enjoy open play, crafts and dancing with CMEE’s resident DJ. Admission is $5 for museum members and $25 for nonmembers. Registration is available online at cmee.org. by Staff Writer

Gift-Wrapping Event Set At Publick House

A gift-wrapping event hosted by the Flying Point Foundation for Autism will be held on Sunday, December 21, from noon to 4 p.m. at the Southampton Publick House on Jobs Lane in Southampton. During those hours, volunteers will be available to wrap holiday gifts in exchange for a donation in any amount. As part of the event, the Southampton Publick House is offering a complimentary glass of wine or draft beer for those who bring gifts to be wrapped. For more information, text 631-255-5664. by Staff Writer