Frank Tassone was a mythic figure in New York’s Roslyn school district, where he served as superintendent. The charismatic administrator allegedly insisted on personally meeting each and every new student. He made a point of regularly lunching with high school pupils. He even led a book club for the district’s parents.
But there were details about Tassone—played by Hugh Jackman in Bad Education, a drama premiering this weekend at the Toronto International Film Festival—that didn’t add up. Details that might have worried the district’s parents and staff members, had Tassone not been so charming and seemingly devoted to his students. He drove a Mercedes, for example. He wore sharp suits and served lobster tails at a luncheon. And puzzlingly, in spite of increasing budget requests, which seemed to always be met, the school roof continued to leak.
Tassone was eventually arrested in an $11.2 million larceny scandal, shocking Roslyn. In the aftermath, details about Tassone’s surprising double life began leaking out into the press. Though Tassone claimed to have been a widower to a woman—reportedly keeping an old wedding photo in his office—he was in a domestic partnership with a man. (“Many Roslynites” reportedly suspected Tassone could be gay.) While playing the role of devoted superintendent, he was also siphoning off $2.2 million on vacations to the Caribbean, gambling trips, rent on an Upper East Side apartment, weight-loss treatment, and dry cleaning. The once proud Long Island school district soon became the subject of tabloid interest. And this weekend, 15 years after the arrest, a big-screen adaptation of this painful chapter of Roslyn’s history will make its way to the Toronto Film Festival.
Making the premiere even more surreal for the Long Island town, however, is the fact that Bad Education was written by one of Tassone’s former charges: Mike Makowsky, who was a Roslyn middle school student when Tassone was arrested in 2004 for first-degree larceny.
“Frank Tassone was the first person I met in Roslyn,” Makowsky told Vanity Fair last month, recalling his introduction, at age six, to the man who would become the subject of his screenplay decades later. After working on a couple independent films, explained Makowsky, “I wanted to write something more personal about my hometown...and this story was ostensibly the biggest thing that has ever happened in it.”
Tassone held a unique place in the Roslyn ecosystem, said Makowsky. “He had been in the Roslyn school district for 10 or 12 years—and in that time, he had grown the school district to this point of national prominence...which meant that the town itself was doing well because the regard of a school district is directly tethered to things like property values.”
But with greater prosperity came greater pressure. “The administrators were asking for more and more money, and, because they were doing an incredible job, the tax payers were happy to oblige,” he continued. “All their kids were getting into amazing schools and doing great on their SATs, and property values in the town were going up. So it was a really sort of complicated, awful thing: This very affable, charismatic person who placed a real emphasis on the quality of education and helping students, then at the same time, you hear that he’s been taking money from the coffer and was part of this $11.2 million [larceny] scheme. It really shocked everyone in my community, and there were these really deep-seated feelings of betrayal.”
Tassone was not acting alone; the Roslyn schools’ former business administrator, Pam Gluckin (played in the film by Allison Janney), admitted to stealing $4.3 million herself. She and Tassone also reportedly withdrew over $1 million from ATMs. “The school district was paying for the renovations to her home in the Hamptons,” said Makowsky. “Her son had a district credit card that he was using to buy construction materials from home-supply stores. She bought Jet Skis, dog food...meanwhile Frank was going to Vegas like two or three times a year on the school district’s dime.”
Tassone was released from prison in 2010, after serving roughly 3 years of a 4-to-12-year prison sentence. But Makowsky opted not to reach out to his former superintendent when writing his screenplay, instead speaking to teachers, PTA members, and other tax payers who had interacted with Tassone, and were still trying to grapple with the complexities of his actions over a decade later.
“I know the film is called Bad Education,” said Makowsky. “But it’s a bit of a misnomer in that regard.... I had an incredible education there. And I think it’s in large part, strangely, due to this man, Frank Tassone, who recruited most of the teachers I had. We were one of the top-ranked schools in the country when Tassone was arrested.”
Bizarrely, Bad Education’s premiere happens to conflict with Makowsky’s 10-year high school reunion. But the screenwriter is hopeful—if cautious—about bringing his film back to Roslyn during his next homecoming. “I’m sure that there’s a segment of the community that would rather this thing just disappeared. But it feels like a story—to me, at least—that’s eminently worth telling.”
“It’s a strange thing,” Makowsky continued. “How can you care so deeply about the students, education, and devote your whole life and career to this very noble profession...but at the same time, take in such an egregious way from the students, from the community, from the tax payers?.... I’m still kind of hopeful for a greater dialogue.”
