Genre: Drama
Director: J.C. Chandor
Writer: Lon Charles
Cast: Matthew McConaughey, Alison Tolman, Spike Jonze, Anthony Michael Hall, Nathan Fielder, Michael Chiklis, Hope Davis, Tony Hale
Plot: Frank Tassone (Matthew McConaughey) sits in his office at offices of the Roslyn School District - on the North Shore of Long Island, New York. His assistant superintendent for busines, Pam Gluckin (Alison Tolman), has just been escorted from the building by police - charged with stealing over $250,000 from the district. The school board members are impatiently waiting in the district's conference room, waiting for Tassone to tell them what to do.
That night, at an emergency school board meeting, Tassone makes an eloquent argument for compassion and leniency. He describes her as a desperate woman with a failing marriage and health problems. He asks them to picture their own child in the situation. He tells them that if the board chooses not to press charges, she has agreed to quietly resign, give up her administrator's license, and give back the money. Some board members wonder aloud if they have a moral obligation to throw the book at her, Tassone warns them that if this situation is not handled gingerly that it could take years to go away. He reminds them that she is a tenured employee who, if the board presses charges would collect $160,000. But if she resigns on her own, they would keep that money plus the money she stole.
Some board members ask if it is even legal to let her go. Tassone tackles that question by introducing a criminal lawyer he has brought to the meeting, Tom Hession (Spike Jonze), a former Nassau County prosecutor. He advises the board that as a matter of law, victims of embezzlement do not have to press charges. Tassone assures the board that no good could come from going public.
When he first arrived in Roslyn, Tassone was like a rock star. He single-handedly turned Roslyn High School into one of the top five schools in the country. After just a couple years on the job, the Roslyn Rotary Club names him Man of the Year. He accepts the award at the ceremony, and gives a speech about how the real winners are the teachers and faculty of the Roslyn School System. During a work lunch, Tassone pontificates about how the school district should act like any private corporation with an $80 million budget and compares his job to that of a high-powered CEO. Tassone meets Gluckin, the district's treasurer. He takes an immediate liking to her, as she becomes his closest confidant around the office. He eventually promotes her to Assistant Superintendent for Business, one of the top positions in the whole district, putting her in charge of the district's accounts.
One day not long after Gluckin's arrest, Tassone comes across a letter on his desk. It talks about how Tassone participated in the embezzlement scandal to support his lavish lifestyle, with the help of Gluckin. He looks at the envelope and discovers that it was a letter returned to school district after failing to be sent to a city council member. Tassone immediately calls Charlie Piemonte (Anthony Michael Hall), assistant superintendent for curriculum and instruction, into his office. Tassone shows Piemonte the letter and tells him that none of it is true.
The D.A. launches an investigation into the embezzlement, and Tassone suggests bringing in Andrew Miller (Nathan Fielder), the accountant who noticed the missing $250,000, to go through the Gluckin's books with a fine-tooth comb. This time around, Miller finds a complicated web of embezzlement involving phony companies, eventually discovering the amount of missing money is closer to $1 million.
The media catches wind and criticizes the school board for allowing Gluckin to mearly resign instead of pressing charges against her. Tassone comes to the board's defense, insisting that they were all betrayed by Gluckin, himself included. The community rallies behind Tassone, insisting that he could never have knowingly let Gluckin steal the money, with many pointing out that he turned their high school into one of the nation's best.
At the next school board meeting, Tassone once again tries to explain why they let Gluckin resign without pressing charges, this time passing the blame onto the accountant and the lawyer who had advised the board. He insists that had they known everything they know now, a different course of action would have been taken.
Tom Hession, the attorney who had advised the board, tells the media that he had simply told the board what was legal, not ethical. Andrew Miller is forced to defend himself, noting that his job duties aren't to be looking for fraud, just irregularities.
School board president Bill Costigan (Michael Chiklis) goes into Frank Tassone's office and asks where he had found Hession in the first place. Tassone says he was referred by the district's usual lawyer. Costigan makes some phone calls and quickly finds out that this is untrue, and that Tassone personally brought in Hession. Costigan barges into Tassone's office to demand answers. Tassone begins stammering, this time telling Costigan that somebody else must have referred him to Hession, but that he can't remember exactly who.
Soon, Tassone's office is under siege. More and more of Gluckin's financial records are turning out to be complete fiction. The newspapers are going crazy, trying to uncover every shred of information they can. Tassone spends more and more time away from the office, with rumblings beginning that he's gone into hiding. The media releases information that his cell phone records show that he has been jetting to Puerto Rico, California, and Florida, as well as having taken multiple trips to Las Vegas recently.
Costigan receives a phone call from a district lawyer telling him to call Andrew Miller as soon as possible. Miller tells Costigan that the have uncovered well over $1 million in missing money, and that he thinks it involves Tassone. They meet in person, where Miller shows Costigan records that the school district had paid for Tassone's rent, car, jewelry and even skin treatments due to Tassone padding his expense account with outrageous numbers for things like dry cleaning.
Costigan demands to meet with Tassone, and brings along a school board member as a witness. The exchange gets heated as Tassone refuses to explain himself other than to state that his contract covers all reasonable expenses. Costigan then angrily suggests Tassone resign. After the meeting with Costigan, Tassone fires Andrew Miller, but not before Miller totals the missing money to $5 million. Tassone also fires the district's lawyers.
At the next PTA meeting, parent Faith Russo (Hope Davis) tells Tassone that they have always supported him, but that he isn't making things look good by constantly changing his story, trying to pass all the blame onto others and firing district employees. She asks him if there are updates on the planned lawsuit against Gluckin from the district. He says that only the law firm has that information, and she asks if it's the same law firm he just fired. Tassone blows up on her, yelling at her to listen to him and questions her knowledge of the law. Russo then informs him that she is a lawyer, which shuts Tassone up. He then storms out of the auditorium.
Anthony Annunziato (Tony Hale), Gluckin's replacement as assistant superintendent for business, manages to connect the scandal directly to Tassone on his first day on the job when he looks into a company called WordPower that had collected nearly $1 million dollars from the district, mainly for word processing services. He simply searches the company on the internet and discovers that the address listed for the company is Tassone's home address. Annunziato calls Tassone, who is down in Florida, to ask why the company is listed at his address. Tassone insists they simply have an office in his building and that's how he found out about them. Tassone tells Annunziato that they have to find the proper way to spin that information, but Annunziato isn't sure it can be done.
With the new information, Costigan calls an emergency school board meeting. Tassone finds out about the meeting while he is still in Florida and calls Costigan, coolly insisting that the board doesn't meet without the superintendent. Costigan reminds Tassone that he said he'd be home today. Tassone comes back home a couple days later and is immediately relieved of duty by the school board. The board then starts cleaning house, firing employees who appear to have conspired with Tassone.
The board presses charges against Frank Tassone. He is convicted of fraud and sentenced to 4 to 12 years for fraud. The total amount of money that was embezzled by Tassone and his accomlices ends up totalling $11 million. Gluckin was also convicted in a separate trial for stealing $4.3 million. Every district employee fired for their involvement received their full pensions - with Tassone collecting $173,495 a year, even while in prison. Tassone was released after serving just 4 years of his sentence. Pamela Gluckin received parole a year later, receiving a pension of $21,000 a year.
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