Frank Tassone, head of one of the richest US education authorities, was jailed last week for his part in embezzling more than $11 million (pound;6m) of school funds.
Mr Tassone was superintendent of the Roslyn school district on Long Island, home to some of New York's wealthiest commuters. He personally siphoned off more than pound;1 million, splashing out on a lavish Manhattan flat, gambling sprees and trips to London on Concorde.
He is also said to have given "sweetheart contracts" for jobs to a boyfriend in New York, while sharing a house in Las Vegas with a male stripper.
Mr Tassone was described by the judge as a "traitor" in the battle to guide and counsel children and jailed for at least four years.
Before his criminal activities became known, Mr Tassone was a popular figure on Long Island. He once placated teachers who complained about their headteacher by sending them T-shirts printed with the message "2 TEACH + 2 TOUCH LIVES = 4EVER".
Brought up in a slum area of the Bronx, Mr Tassone completed a doctorate in educational administration, writing his dissertation on Charles Dickens.
Angry parents have turned his interest in Dickens against him by comparing him to the Martin Chuzzlewit character Seth Pecksniff, the corrupt architect determined to seize a share of the Chuzzlewit family fortune.
"I am sincerely sorry for what I have done," Mr Tassone told the court, dressed in orange prison clothing. He said he hoped to continue his "ministry of teaching" in prison to atone for his past.
The authorities have recovered only pound;4m of the missing pound;6m.