MINEOLA, N.Y., Sept. 26 - The former Roslyn schools superintendent, a once-revered figure whose academic credentials and contacts with Ivy League admissions offices seemed to make him the ideal guardian of a wealthy district's aspirations for its children, pleaded guilty on Monday to stealing $2 million from the school system over six years.
In a courtroom here filled to capacity with irate parents and P.T.A. presidents, many of whom booed when he entered the room, the former superintendent, Frank A. Tassone, 58, agreed to cooperate in a wide-ranging criminal investigation of thefts from the district by others - an alleged pattern of pilfering that State Comptroller Alan G. Hevesi has described as "the largest, most remarkable, most extraordinary theft" from a school system in American history.
Altogether, an estimated $11 million was stolen from the district in a scheme that involved some of the top administrators, according to prosecutors. Dr. Tassone agreed to pay back his share, $2 million.
Dr. Tassone is so far the first of five defendants, including his companion, Stephen Signorelli, 60, to resolve the criminal charges against him.
In exchange for his cooperation, District Attorney Denis Dillon promised to recommend that Dr. Tassone, facing as much as 25 years in prison on multiple counts of grand larceny and fraud, receive a maximum term of 4 to 12 years. Dr. Tassone will pay the money back according to a schedule still to be worked out with the district attorney's office.
Roslyn residents at the hearing widely criticized the proposed plea deal. Many demanded that Dr. Tassone serve a full 25-year term, not just for the damage he caused to the district's finances but for the impact they said his crimes had - and continue to have, some 16 months since his forced resignation - on Roslyn's sense of community.
"He has done great damage to this school community," said Judi Winters, a longtime civic activist in Roslyn. "It's a moral issue, not a dollar issue." Like others, she described a community divided over the question of what a school board should be: education watchdog or fiscal watchdog.
"You get the feeling there is an angry mob" mentality driving local school board politics now, said Chris Messina, a parent. "It's made a lot of people feel reluctant to get involved."
In a statement he read in a whisper before Judge Alan L. Honorof of Nassau County Court, Dr. Tassone apologized for the harm he had done, though as many in the courtroom later complained, he seemed to portray himself as one of his own most deeply wounded victims.
"During the past year and a half," Dr. Tassone said, "I have reflected daily on the mistakes I made in the last few years after a 35-year outstanding career in public education. These egregious errors have irreparably damaged, if not destroyed, my career in public education. I cannot adequately explain the pain my errors have caused me."
"I will make restitution to the Roslyn schools, and I am sorry for my poor judgment," he said. "I only hope and pray that someday the Roslyn community will remember the good I did for the district as well as find it in their hearts to forgive me for my mistakes."
The $2 million Dr. Tassone admitted to stealing paid for vacations, meals, dry cleaning bills, furniture, dermatology treatments, car loans, real estate investments and personal expenses averaging about $20,000 a month in some years. In a separate admission, he said he submitted $219,000 worth of fake invoices on behalf of his partner, Mr. Signorelli, for the printing of school handbooks.
As part of his cooperation deal, Dr. Tassone is expected to give evidence against Mr. Signorelli, with whom he has shared a Manhattan apartment for many years.
According to the district attorney's office, the $11 million theft was carried out by a small group of Roslyn district employees, including the assistant superintendent of finance, Pamela Gluckin, who is charged with using school money to pay for her personal mortgage loans, car loans, home computers and water bills.
By almost all accounts, Dr. Tassone's ability to defraud the school system, in retrospect, seemed to be of a piece with his ability to charm, ingratiate and forge ties with school board members, fellow administrators and especially, parents, district residents said.
He kept his door open to unscheduled visitors, entertained requests for favors, wrote a regular column for the local weekly newspaper and led a reading group on the novels of Charles Dickens, about whom he wrote his doctoral dissertation at Teachers College of Columbia University.
"He had all the right credentials, the right vocabulary," said Judy Birnbaum, a past president of the East Hills Elementary School P.T.A. "He did so many people favors that if anyone said a word against him, there was always a defender saying, 'Oh, no. Not Mr. Tassone. He wouldn't do that.' "
Parents eager to win admission for their children to Ivy League schools were reassured by Dr. Tassone, several parents have said, that his letters of recommendation would give their applications a big help. Whether by his intervention or not, the 95 percent of Roslyn students who graduate from its high school include a high number entering the nation's top colleges.
The Roslyn scandal, which so far has implicated Ms. Gluckin, two other former school employees and the principal of an auditing firm, Andrew Miller, has had a significant impact on state oversight of local school districts.
State audits of the districts were largely discontinued in the 1980's to save money. But since the Roslyn fraud was revealed, financing has been reinstated to conduct regular audits of all 700 of the state's school districts outside New York City, where audits are conducted by the city comptroller's office.
In Roslyn, a suburban community 20 miles east of Manhattan where lawyers, accountants, small-business owners and teachers comprise a substantial portion of the residents, anger over the scandal is sometimes mixed with a sense of effrontery at having been bamboozled by scammers.
"I'm a teacher," Mrs. Birnbaum said. "I was on the committee that interviewed him. He was very impressive. Yes, we were deceived and cheated."
Some parents have begun circulating a petition demanding that Dr. Tassone receive a stiffer sentence. It will be presented to the judge at Dr. Tassone's sentencing, which is scheduled for Nov. 29.
Others, however, said Dr. Tassone's restitution, his cooperation in the continuing investigation and a minimum of four years in state prison seemed like a fair settlement of his debt to the community.
"It doesn't really matter much to me whether he's really sorry or just saying he's sorry, " said Rebecca Katz-White, a resident and parent who attended the hearing yesterday. "I'm a former criminal defense attorney who has been inside of a lockup. I feel that four years in prison is a long, long time."