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The Bad Superintendent

To the Harvard-obsessed parents of Roslyn, New York, Frank Tassone appeared to be the ideal schools chief. Then $8 million went missing, Tassone became a prime suspect, and the details of his secret double life began to emerge.


Tassone after his July 6 arrest.  

For the first time in his long, charmed career, Frank Tassone had a problem. The erudite, widely admired superintendent of the Roslyn, Long Island, school district—the North Shore public-school system he had managed to make, based on test scores, one of the ten best in America—found himself confronted in the fall of 2002 with a rather awkward, potentially embarrassing situation. His assistant superintendent for business had been caught stealing $250,000, writing school checks to cover her credit-card bills and impetuously racking up mammoth purchases at a Home Depot several towns away. And the school-board members were sitting in the district’s conference room, waiting for Tassone to tell them what to do.

If you want a job where you get blame for everything, credit for nothing, and no real reward, try running for the Roslyn school board. Everyone on the North Shore has a child who is a genius, or demands extra attention, or has a guidance counselor who needs some sense talked into him. In darker moments, it’s you against the community you hoped to serve, with only the superintendent—the pro—to help you with the tough decisions. The pro, in this case, was Tassone, always dressed in the freshly pressed wardrobe of a CEO, with the academic pedigree and easygoing authority of a literature professor. That night, Tassone made a moving, eloquent argument for compassion and leniency. The culprit, Pam Gluckin, had tearfully confessed, he said. Her marriage was falling apart, she was ill, she’d been desperate. And if the board didn’t press charges, she’d agree to quietly resign, give up her administrator’s license, and give back the money right away.

Not everybody went for it at first. Some board members wondered if they had a moral obligation to throw the book at her. But Tassone warned that if this sort of thing wasn’t handled gingerly, it could take years to go away. Gluckin was a tenured civil-service worker who made $160,000. If the board pressed charges, she’d keep earning that money for years as the case crept through the courts. But if she left on her own, Roslyn could save that money and get back what it lost. No harm, no foul.

Others wondered if letting her go was even legal. So it was something of a relief that Tassone had thought of this, too. He had asked a criminal lawyer, a former Nassau County prosecutor, to come to the meeting—and that lawyer advised them that as a matter of law, victims of embezzlement didn’t have to press charges.

As the board had come to expect of him, Tassone was putting into words what they knew, but didn’t know they knew. Roslyn may be no wealthier than Great Neck or Syosset or Jericho, but its schools were seen as the best. A diploma from Roslyn High School is the closest you can get on Long Island to a ticket to Harvard; every year, a quarter of the seniors get into highly selective colleges. Did they want camera crews on school grounds, or auditors sniffing around the district office? Would Ivy League admissions officers look at Roslyn students the same way? What, Tassone said, would happen to property values?

His message was clear: No good could come from going public. Voters could hardly be expected to reelect school-board members who’d let something like that happen in a place like this.

And he was probably right. But what the board couldn’t have known was that Tassone was not just protecting Pam Gluckin. He was also protecting himself.

The seemingly monastic bachelor, it appears, was living with one man in Manhattan while owning a house in Las Vegas with a 32-year-old male exotic dancer.

Clustered in a wooded enclave of Levittown-style homes mingled with compact mansions on tiny lots, the villages of Roslyn and East Hills make up an enlightened community with forward-thinking public schools—the first on Long Island with free condoms in a jar in the health room, one of the first in the state with a community-service requirement for high-school graduation. At least one student has parked a Hummer in the Roslyn High School lot, and a flat-screen TV posts schedules in the halls. Parents are so determined to buff their kids’ transcripts that the high school now offers honors classes to any student who wants them. In April, the Wall Street Journal called Roslyn High the sixth-best public high school in America, not far behind Stuyvesant and Hunter.

Then, in May, the roof fell in. According to Nassau County prosecutors, Frank Tassone had spent his twelve years in Roslyn quietly running one of the most audacious scams ever to afflict a public-school system. The coffers were plundered in practically every imaginable way—expense-account padding, vendor-bidding violations, check-record fabrications, even the creation of phony businesses. Tassone allegedly had the district pay for two trips to London on the Concorde, one for $20,000 and another for $30,000, including $1,800-a-night suites, and a half-dozen jaunts to Las Vegas with his friends—including Roslyn High’s popular principal, Jay Stoller—where the district even staked some of Tassone’s gambling money. The D.A. says that by the time he was arrested on July 6, Tassone had saved enough money to transfer $300,000 to bank accounts in his sisters’ names.

Both Tassone and Gluckin have been arrested for first-degree larceny, and the court has frozen their assets as they await indictment. But it’s doubtful Roslyn will ever get back what was lost. There’s a reported $8 million missing, and the district attorney’s auditors haven’t finished counting. After a wave of other resignations, the D.A. says more arrests may be on the way.

What’s just as surprising to the parents and teachers of Roslyn is that Tassone had been living something of a double life. The seemingly monastic bachelor who had an old wedding photo on a shelf in his office—and spoke wistfully of the young woman he married who died of cancer—turned out, it appears, to be living with one man in Manhattan while owning a house in Las Vegas with a 32-year-old male exotic dancer. Now, at the start of a new school year, parents are left wondering what, if anything, was real about the man who won their trust and made their schools the envy of Long Island. How could a twelve-year, $8 million scam go down right under their noses? And perhaps most troubling: Did Frank Tassone deceive Roslyn, or, out of a desire to give its children the best, did Roslyn allow itself to be deceived by Frank Tassone?

Being the head of a wealthy school system is a little like being the headwaiter at Alain Ducasse. You’re at the top of your profession, but at the end of the day, you’re still a waiter. “Working here is about client satisfaction,” says Charlie Piemonte, Roslyn’s assistant superintendent for curriculum and instruction. “The concerns people have for their kids are serious at a very young age. It’s like a business. They put their kids on a path—if you’re in a gifted program, if you get the teacher everybody loves, if you get A.P. classes. It’s an untenable job.”

Tassone, however, made it look easy. “Frank was really the master,” Piemonte says. “I mean, this guy was loved. He walked on water.”

From the moment he arrived, Tassone understood that in a place like Roslyn, parents expected the schools to be more than just the stewards of education—they also had to be shimmering reflections of the community. His own credentials were certainly first-rate. Brought up in a rowhouse in the Pelham Bay section of the Bronx, Tassone went on to earn a B.A. from Iona College in Westchester and then two master’s degrees—in educational administration and languages and literature—and a doctorate in educational administration at Teachers’ College, where he wrote his dissertation on Dickens. He worked as an administrator in Westchester and Levittown before landing in Roslyn in 1992.

Every new program Tassone started played into Roslyn’s sense of pride—or, perhaps, vanity. He brought foreign-language classes into the elementary schools, and a “values education” curriculum to the high school, including the community-service requirement. He embraced senior citizens by starting discussion groups and hosting an annual community dinner-dance—scheduled, shrewdly, right before the annual vote on the school budget. School employees learned to look forward to birthday cards signed “Dr. Tassone,” and congratulatory gift baskets on anniversaries. And he disarmed potential dissenters face to face, meeting by meeting—sitting still as an owl at his office’s conference table, hands folded in his lap, head nodding.

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