The beloved superintendent of New York's Roslyn school district and his staff, friends and relatives become the prime suspects in the unfolding of the single largest public school embezzlement scandal in American history.
A Long Island school superintendent and his assistant are credited with bringing the district unprecedented prestige. Frank is a master of positive messaging, whether before an audience of community leaders or in an office with a concerned student or parent. That changes when a student reporter uncovers an embezzlement scheme of epic proportions, prompting Frank to devise an elaborate cover-up.
In 2002, Dr. Frank Tassone (Hugh Jackman) is the superintendent of Roslyn School District in Long Island, which oversees Roslyn High School. Frank, along with his assistant superintendent Pam Gluckin (Allison Janney), have overseen major improvements in the district, becoming the 4th ranked public school in the country. The school's performance in turn stimulates the local economy, including for school board head and real estate broker Bob Spicer (Ray Romano). Frank is beloved by students and parents, and sought after by women; Frank claims to have lost his wife several years ago, but is in fact a gay man. While attending a conference in Las Vegas, Frank begins a relationship with former Roslyn student Kyle Contreras (Rafael Casal).
While writing an article for the Roslyn school paper about a sky-walk the school is planning to construct, student Rachel Bhargava (Geraldine Viswanathan) begins to discover discrepancies in the school district's finances. Unbeknownst to anyone at the school, Frank and Pam are co-conspirators in a massive embezzlement scheme, defrauding the school district for millions of dollars. Pam's part in the scheme is discovered when her son Jimmy (Jimmy Tatro) uses a Roslyn expense card to purchase building materials for Pam's home renovations; the purchases are noticed by a relative of Bob, who alerts him to the purchases.
The next day, Pam is confronted about her actions. In an effort to cover up his part in the scheme, Frank convinces the school board to conceal the embezzlement from the public and from law enforcement (as this will affect the school ranking, the future budget and most importantly the real estate prices in the area). He also convinces Phil Metzger (Jeremy Shamos), the district's auditor, to estimate the amount stolen at around $250,000, despite the actual amount possibly being far higher. Pam is fired from her job, but given the opportunity to resign quietly and make restitution rather than having her misdeeds exposed. Frank also transfers Pam's niece Jenny (Annaleigh Ashford), who works for the district, into a 'special utilities' role, threatening to expose her own misuse of district funds.
Meanwhile, Rachel begins to uncover evidence of the embezzlement in the form of supply orders that were never fulfilled and consulting fees paid to unknown companies. She travels to Manhattan to investigate one of these unknown companies. When she arrives at the registered address she finds it is not an office but an apartment building. As she is leaving the building, she spots Frank entering the same apartment; the two see each other, but Rachel quickly leaves. The apartment in fact belongs to Tom Tuggiero (Stephen Spinella), Frank's long-time partner; Tom is also the registered owner of the fraudulent company.Frank meets with Rachel and warns her of the potential fallout for exposing the story. Phil confronts Frank about more illegitimate expenses, including first class airline tickets for Frank and Kyle. Frank threatens to expose Phil's failure to catch the original embezzlement, who agrees to maintain the cover-up, but it is too late - Rachel's story is published in the school paper, implicating Frank as the key figure in the scheme. Frank defends himself to Bob, saying that he had the school's best interests at heart.
Frank pleads with Bob not to expose the board's failure to report Pam's original embezzlement until the school budget is approved, but is unsuccessful. The investigation becomes a criminal matter; Pam, Jenny, and Phil are all arrested. After the authorities threaten to prosecute her husband and children, Pam agrees to testify against Frank and turns over evidence of the scheme. Tom is informed by the authorities about Frank's infidelity with Kyle. Frank resigns as superintendent and flees to Nevada with tens of thousands of dollars in cash, staying with Kyle at a house Frank bought for him. Eventually, police arrive and arrest Frank, and he returns to New York, where he is sentenced to prison. While in prison, Frank fantasizes about being back at Roslyn, where he is being congratulated for bringing the school to being ranked #1 in the country.An epilogue reveals that Frank was convicted of embezzling $2.2 million and sentenced to 4-12 years in prison. Pam, who plead guilty to embezzling $4.3 million and testified against Frank, was sentenced to 3-9 years in prison. However, due to an oversight in the state pension fund, Frank will still receive over $173,000 per year.
