MINEOLA, N.Y. (AP) – For years, ex-Roslyn schools chief Frank Tassone stole millions of dollars in taxpayer money to finance everything from his breakfast bagel to European jaunts on the Concorde.

His next journey on the taxpayers’ dime will be to prison.

Tassone, 58, of Manhattan, pleaded guilty Monday to one count each of first- and second-degree grand larceny before Nassau County Judge Alan Honorof in a scandal that state Comptroller Alan Hevesi has called “the largest, most remarkable, most extraordinary theft” from a school system in American history.

As part of a plea deal with prosecutors, Tassone will spend 4 to 12 years in prison and will pay back an estimated $2 million. If convicted at trial, he could have faced up to 25 years.

So far, five people, including Tassone, have been charged in the scandal at one of Long Island’s most prestigious school districts. Prosecutors have said they anticipate further arrests, and Tassone will cooperate in the continuing investigation, District Attorney Denis Dillon said.

About 50 district residents booed Tassone as he entered the courtroom. Many, including former school board president William Costigan, said afterward they were dissatisfied with the penalty Tassone was promised.

Speaking barely above a whisper, Tassone read an apology in court. “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.”

An audit by Hevesi earlier this year found that $11.2 million had been pilfered from the school district between 1996 and 2004, although prosecutors have only been able to link slightly less than $7 million to the current defendants.

Sentencing was set for Nov. 29, but will likely be postponed while Tassone works with investigators, Dillon said.

The fifth person accused in the scandal is the district’s former independent auditor, Andrew Miller, who prosecutors say helped cover up some of the pilfering. At a press conference, Dillon said Tassone provided information that led to the charges against Miller and suggested the ongoing probe “may lead to information on the 50 or more school districts that he audited across Long Island.”

The $2 million taken by Tassone paid for flights aboard the Concorde for vacations in England, cruises, hotel and resort accommodations, dermatology treatments, furniture, jewelry and meals. More than $1 million allegedly was stolen via ATM cash advances and prosecutors said the defendants even had their dry cleaning and cable TV bills picked up by taxpayers.

Records show that Tassone and the district’s former assistant superintendent for business, Pamela Gluckin, withdrew the district’s money from ATMs almost every day between February 2001 and October 2002, with Tassone taking out a monthly average of $21,747.

Tassone is the first of the defendants to settle criminal charges.

Still awaiting trial are Gluckin, 59, of Bellmore, who is accused of more than $4 million in thefts; and her niece, Debra Rigano, 46, of Mamaroneck, a former account clerk, accused of taking more than $780,000. Stephen Signorelli, 60, who shares an apartment with Tassone, is charged with helping the former administrator steal at least $219,000 by submitting phony and padded invoices for the printing of school handbooks.

The schools in Roslyn, 20 miles from Manhattan, are among the best in the state. The district, where homes frequently sell for millions, sends 95 percent of its high school graduates to college, and SAT scores are among the best in the nation.