Former Riverhead High School principal Charles Regan leads members of the school board and administrators in a procession at the high school graduation ceremony in 2017. File photo: Denise Civiletti

A former Eastport High School student has filed a federal lawsuit against disgraced Riverhead principal Charles Regan, the Eastport school district and school officials alleging that when Regan was a teacher in Eastport between 1997 and 2002, he “groomed” her and another child for sexual relations and had sexual relations with them both.

The plaintiff filed the action in U.S. District Court Sept. 18, using the pseudonym “Jane Coe” because she is “reasonably in fear of her health and safety” should her identity be disclosed. The court will have to give its permission to allow the case to move forward without the woman’s identity being disclosed.

The complaint alleges that Regan, a special education teacher who was also the coach of the girls basketball team — of which the plaintiff was a member — groomed her from the age of 13 to cause her to look up to him, trust him and view him as a mentor.

It accuses Eastport school officials at the time of failing to adequately supervise Regan and failing to sufficiently investigate a complaint made about Regan’s behavior by the plaintiff’s mother.

One of the Eastport school officials named as a defendant in the new lawsuit was also named as a defendant in the federal lawsuit filed last month by a former Riverhead High School student: former Riverhead High School principal James McCaffrey.

McCaffrey was the principal at Eastport High School between 1999 and 2002, according to the complaint, when Regan allegedly had sexual relations with the plaintiff. A veteran teacher and administrator in the Half Hollow Hills School District, McCaffrey was the principal at Eastport High School before he was hired by Riverhead as an interim principal in the fall of 2005.

Regan left Eastport for Riverhead in 2006, when he was hired as an assistant principal, working under McCaffrey. McCaffrey was replaced in 2007 by David Zimbler. Zimbler was succeeded by David Wicks in 2011. After Wicks was named assistant superintendent in 2013, Regan was promoted to principal.

Regan, 48, resigned last month, but his resignation is not effective until Sept. 27. He has been on home assignment since April 30, after Riverhead officials learned of Regan’s relationship with a female high school student that included sexually charged and sexually explicit text messages and allegedly forcibly kissing the student in his office on on April 29.

The Riverhead student’s lawyer, John Ray of Miller Place, is also representing the plaintiff in the Eastport case, who is today 35 years old. A second Eastport student, whom the new complaint refers to and whom Ray made reference to in a May press conference, is not willing to come forward, Ray said today. The court filing was first reported Saturday by the News-Review.

According to the complaint filed last week, Regan drove the plaintiff, then 16, to a Knicks basketball game in his car, bought her beer, causing her to become intoxicated, took her back to his home and coerced her into performing oral sex for him. She was 16 at the time. He had the student buy the game tickets and reimbursed her the cost and he instructed her to lie about her whereabouts that night.

The student’s mother complained to school authorities that the teacher had her daughter out all night, according to the complaint, but the district did not conduct an adequate investigation and took no action against the teacher, the complaint states. On at least three subsequent occasions, Regan had sexual intercourse with the student, it says. She was a minor on at least one of those occasions, according to the complaint.

The complaint also alleges that Regan sexually assaulted and raped another female student in Eastport, who was then 14.

Riverhead school officials brought Regan up on disciplinary charges in June, after the Riverhead student went public with her accusations, with her lawyer releasing sexually explicit text messages and partially clad selfies sent by Regan to the student, who was an 18-year-old high school senior.

The charges are terminated by the principal’s resignation, Riverhead school district officials say they filed complaints with the State Education Department and have urged the state agency to revoke Regan’s licenses and certifications.

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Denise Civiletti
Denise is a veteran local reporter, editor, attorney and former Riverhead Town councilwoman. Her work has been recognized with numerous awards, including investigative reporting and writer of the year awards from the N.Y. Press Association. She is a founder, owner and co-publisher of this website.Email Denise.