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.
The film is based on the true story of the largest school embezzlement scandal in history.
On Long Island in 2002, Frank Tassone is a well-liked superintendent who is credited for Roslyn High School’s success, though he strives to take them to the top. However, after assistant superintendent Pamela Gluckin is found guilty of embezzling money from the school’s budget for her and her family’s own expenses, Frank does his best to sweep it under the rug to not tarnish the school’s good name.
A student journalist, Rachel Bhargava, does her research into the school’s budget, leading her to discover a trail of embezzlement that leads right back to Frank. He catches wind of her snooping and tries to deter her from breaking the story, but after being inspired by her father, Rachel convinces the head of the school’s paper to help her break the scandal story. Frank is soon discovered of his guilt and is arrested, along with Pamela, plus her niece and husband. It is also found out that Frank was having an affair behind his husband’s back.
Frank Tassone was found guilty of embezzlement and sentenced to 4-12 years. Pamela Gluckin also found guilty but provided evidence and testimony that got her family out of trouble and left her with a 3-9 year sentence. A total of $11 million was stolen from the school’s budget.
In 2002, Dr. Frank Tassone is superintendent of the Roslyn Union Free School District on Long Island. Frank and assistant superintendent Pam Gluckin 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. 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.
Student reporter Rachel Bhargava is writing an article for the Roslyn school paper about a skywalk the school is planning to construct, and Frank blithely encourages her to treat her article as any top journalist would. Rachel 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, 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 ramifications of a public scandal on the school. They agree to conceal the embezzlement, forcing Pam to pay restitution and resign; the board announces her abrupt “retirement.” Convincing district auditor Phil Metzger to falsify the financial records, Frank appoints him as Pam’s temporary replacement. Frank transfers Jenny to a less visible “special utilities” role, threatening to expose her own misuse of funds when she attempts to implicate him.
Rachel continues her investigation, uncovering evidence of the embezzlement in the form of supply orders that were never fulfilled and massive consulting fees paid to unknown companies, including Pam’s husband’s car dealership. She finds an annual expense of $803,000 to Wordpower Tech and visits its listed 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, Frank’s husband, 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 to London. Frank threatens to place blame squarely on Phil for failing to catch Pam’s scheme and taking part in the cover-up. 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 and flees to Nevada with tens of thousands of dollars in cash, living with Kyle in a house Frank 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 4–12 years in prison. Pam, who pled guilty to embezzling $4.3 million and testified against Frank, was sentenced to 3–9 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.
Long Island, NY 2002 – At Roslyn High School, school board president Bob Spicer (Ray Romano) is delivering a speech to the full auditorium on how they are #4 in the school district. He welcomes superintendent Dr. Frank Tassone (Hugh Jackman), who is to thank for taking the school to the heights it has reached. Frank is welcomed to a cheering crowd.
Frank is well-regarded and admired by his peers and students. He goes to work and meets with a mother named Carol Schweitzer (Stephanie Kurtzuba), who wants Frank to help get her son Chad (Calvin Coakley) to get into a prestigious school (OMNI). Frank gives the boy some inspiring words before leaving him and his mother. When Frank returns to his office, he is met by the high school’s journalist Rachel Bhargava (Geraldine Viswanathan). Frank knows her because he used to teach her older brother. Rachel asks him about the SkyWalk that the school is getting, which is mostly just a bridge designed to get students around campus a little faster. After Frank answers her question, Rachel gets ready to leave, saying it’s only a puff piece for her since the seniors get the better stories. Frank encourages her to turn it into something bigger if she wants it to be.
Spicer then comes to get Frank for a meeting regarding the school’s budget and how they are coming in compared to the other schools. The other staff gives Frank a gift basket for all his contributions. He then goes to have lunch with assistant superintendent Pamela Gluckin (Allison Janney) where they discuss what people like Spicer make, as well as the plan for Roslyn to be number one in the district with the inclusion of the SkyWalk. Frank also complains about a healthy diet his doctor is making him go on.
Frank goes to a book club that he runs with other women in the area. He speaks to one mother, Sharon Katz (Katherine Narducci) about her son. When Sharon gets emotional, she leans in to try and kiss Frank, who pulls back because he claims the memory of his late wife still lingers with him.
Rachel goes to ask Pam about the SkyWalk for her story. She gives her a quote, but Rachel asks for bids for the project. Pam begrudgingly gives her the keys to the basement to find any records she might want. Rachel goes down there and grabs whatever files she can take, and then asks one of the staff, Jenny Aquila (Annaleigh Ashford), to help make copies. They go to the copy room, which has a leaky ceiling that Rachel cannot help but focus on.
Frank goes on a trip with other coworkers to Las Vegas, where he runs into a former student, Kyle Contreras (Rafael Casal). They catch up, have dinner and drinks, and then go back to Kyle’s place where they start to kiss.
At night, Pam is still at school looking over several personal expenses when she is startled by the janitor. The next day, she hosts a birthday party where Jenny (who is her niece) is attending. She approaches Pam in private to ask if she can borrow some money to buy her son a PlayStation, and Pam agrees to give her whatever she needs. Pam and her friends then focus on her son James “Jim Boy” McCarden (Jimmy Tatro), who is a known screwup and is supposedly getting ready to turn his life around with a new job.
Rachel is shown living with her unemployed father David (Hari Dhillon). She has dinner with him but is doing more to focus on her story. She presents it to the head of the paper, Nick Fleischmann (Alex Wolff), who isn’t impressed with what Rachel has brought him.
James uses Pam’s school credit card to make renovations to the house by buying a bunch of items from Ace Hardware. The school catches wind of the expenses, as well as a whole bunch of other purchases made with the school’s money. When they realize James is Pam’s son from her first marriage, they think this can be traced back to her. Pam soon arrives at the school to be confronted with these revelations. Frank is also called in for this meeting. Pam knows it’s James’s fault, but Jenny admits to using the card for more than just a PlayStation, like major expenses from Lord & Taylor and Macy’s. Pam quietly realizes she’s screwed.
As the staff continues to try and deliberate a solution to the problem, Frank learns that about $220,000 has been funneled out of the school’s budget. Frank tries to calm everyone down and figures out an answer that won’t make them look bad and can be swept under the rug. Everybody goes to Pam to tell her to resign from her position while everyone shames her and finds a way to make her look bad or mentally unstable. Pam tries to call Frank later to explain herself, but he won’t listen to her. She is then forced to go tell her family what has happened and that most of them are also guilty in the embezzlement since they used her school credit card for their own stuff as well. Pam admits her full guilt over it and defends why she did it.
Pam returns to school to clean out her office, where Rachel tries to get a follow-up for her story. Pam ends up snapping at her for prying into issues involving the money being used for the SkyWalk and other expenses specifically for the schools. Later, Jenny stops by Frank’s office to tell him she knows what they did to Pam, and that she knows something about him that others don’t.
Word about Pam’s dismissal turns into a rumor that she was let go due to her ailing health, and people start calling to ask about paying for her medical bills. Meanwhile, Rachel goes to greater lengths to get the information she wants, even talking to other staff members who could provide her with the records she needs. Nick approaches her to remind her of the deadline for her story, then tries to empathize with her over a work issue involving her father, but she brushes him off.
After looking over several records and reviewing with her dad, Rachel eventually finds an address that apparently belongs to Frank. She goes to an apartment in the city where she meets Thomas Tuggiero (Stephen Spinella). After awkwardly assuming she has the wrong apartment, Frank comes up from behind Tom, revealing that they are lovers. They sit for dinner after Tom mentions Rachel stopping by. Rachel brings this info to Nick, but he is worried about repercussions that could impact their careers going forward if they accuse someone like Frank of a serious crime. Frank even approaches Rachel at school during lunch, warning her that going public with something she isn’t entirely sure of can come back to bite her.
Frank is visited by another staff member, Phil Metzger (Jeremy Stamos), who looked into the school’s books and found two first-class tickets from the school’s budget paid for to Frank and Kyle. Frank gets viciously defensive about it and makes Phil leave.
Rachel later asks David about the circumstances surrounding him losing his job. He knew about insider trading going on at his company and is adamant he wasn’t involved in, but he is ashamed of the fact that he didn’t come forward with it sooner since he was too close to the people involved. This gives Rachel the push to do what she knows is right.
Frank walks into work the next day with everyone glaring at him. He discovers that the papers have gone wide with news that he was heavily involved in the school’s embezzlement. He talks to Spicer about it, saying that it was innocent borrowing that got out of hand. Frank has no supporters, and other parents and district employees are furious with him. When he tries retreating to his office after a particularly stressful conference, he finds the Schweitzers there trying to get him to recommend Cal again, but after being forced to listen to Cal botch his own written speech repeatedly, Frank goes off with a cynical tirade that sends the mother and son away.
Pam meets with the District Attorney (Pat Healy) to discuss the terms of her impending sentence, with enough evidence to convict her whole family, but he tells her that if she cooperates, she can save her family. Meanwhile, Frank retreats to find Kyle and spends time with him, going to a nightclub together. After Pam brings the DA more evidence, police go arrest Jenny and Pam’s husband Howard (Ray Abruzzo). As Frank drives Kyle home, he knows he is going down and tells him what to do. Police soon arrive and arrest Frank in front of Kyle.
Tom is brought in for questioning, and it is revealed that he and Frank are married. He then finds out about Kyle and the affair. What follows is Frank’s trial and conviction, and a major fallout that ruins his name and reputation. This goes for other board members like Spicer, who has a woman leave her dog’s poo on his porch. On the bright side of things, Rachel is promoted to editor-in-chief of the school’s paper. Pam is also sentenced to prison time while her family is let go.
In prison, Frank is let out for recreation time when he hears what sounds like Spicer’s voice making a speech. He follows the voice until he walks into the halls and it starts to look like he is back in school. Frank walks into a ceremony to celebrate Roslyn being taken to the #1 position in the school district. He appears to smile tearfully before his face turns into one of full remorse.
The ending text states that the real Frank Tassone was convicted of stealing $2.2 million from the Roslyn school district and was sentenced to 4-12 years in prison. Pamela Gluckin testified against him after pleading guilty to embezzling $4.3 million and was given a 3-9 year sentence. A total of $11 million was stolen from the school’s budget, making it the largest school embezzlement scandal in history. Every paper in the tri-state area reported on the scandal, but only after Roslyn High School’s Hilltop Beacon broke the story first. Due to an oversight in New York State Pension law, Tassone is still entitled to $173,495.04 a year.