In 2002, Dr. Frank Tassone [Hugh Jackman] is the superintendent of the Roslyn Union Free School District on Long Island. He and assistant superintendent Pam Gluckin [Allison Janney] have overseen major improvements in the district, with Roslyn High School becoming the fourth-ranked public school in the country. The school’s performance stimulates the local economy, reaping rewards for school board president and real estate broker Bob Spicer [Ray Romano]. Beloved by students and parents, Frank claims to have lost his wife several years ago, and rejects advances from some of the local mothers. Attending a conference in Las Vegas, he begins an affair with his former student Kyle Contreras [Rafael Casal] whom he meets at a bar.
Student reporter Rachel Bhargava [Geraldine Viswanathan] is writing an article for the Roslyn High School paper about a skywalk the school plans to construct, and Frank blithely encourages her to treat her article as any top journalist would. She investigates the project, to Pam’s irritation, and notices irregularities in the district’s finances. It is revealed that Pam has a fraudulent district expense card, which she encourages her niece Jenny [Annaleigh Ashford], a district clerk, to use. When Pam’s son uses the card to shop for thousands of dollars’ worth of construction materials for her home renovation, Bob is alerted by a relative working at the store.
Bob and the school board confront Pam, realizing she has embezzled at least $250,000 in taxpayer funds. Frank persuades them to handle the matter quietly, detailing the consequences a public scandal would have on the school and community. They agree to conceal the embezzlement, forcing Pam to pay restitution and resign; the board announces her abrupt “retirement.” Convincing district auditor Phil Metzger [Jeremy Shamos] to falsify the financial records, Frank appoints him as Pam’s temporary replacement. He transfers Jenny to a less visible “special utilities” role, threatening to expose her own misuse of funds when she implies blackmailing him.
Rachel continues her investigation, uncovering evidence of the embezzlement in supply orders that were never fulfilled and massive consulting fees paid to unknown companies, including Pam’s husband’s car dealership. She finds a cumulative expense of $803,000 to Wordpower Tech and visits the address, which she discovers is a Manhattan apartment. A man answers the door and Rachel leaves, but she and Frank spot each other when he arrives and enters the same apartment. The man is Tom Tuggiero [Stephen Spinella], Frank’s domestic partner, and Rachel realizes Wordpower Tech is a front created by Frank, a co-conspirator in the embezzlement. Frank later warns Rachel of the potential fallout for exposing the story.
Phil informs Frank of an incriminating expense: Frank used district funds on first-class tickets to fly himself and Kyle by Concorde to London. Phil agrees to keep quiet, but Rachel publishes her story in the school paper, exposing Frank’s key role in the embezzlement. Insisting he acted in the school’s best interest, Frank pleads with Bob not to confirm the scandal until the school budget is approved, but Bob and the school board report the cover-up in its entirety.
Pam, Jenny, and Phil are arrested; when the authorities threaten to prosecute her family, Pam agrees to testify against Frank and turns over evidence of the scheme. Tom is informed of Frank’s second life with Kyle, and Rachel becomes the school paper’s editor-in-chief. Frank resigns, flees to Nevada with tens of thousands of dollars in cash, and moves in with Kyle in a house he bought for him. He is eventually arrested, returned to New York, and convicted. In prison, Frank fantasizes about being back at Roslyn, where he is congratulated for making the school #1 in the country.
An epilogue reveals that Frank was convicted of embezzling $2.2 million and sentenced to 4 to 12 years in prison. Pam, who pled guilty to embezzling $4.3 million and testified against Frank, was sentenced to 3 to 9 years in prison. A total of $11 million was embezzled, the largest school theft in American history. Due to an oversight in state pension regulations, Frank is still slated to receive his teacher’s pension of $173,495.04 per year.
