How Frank Tassone Stole $11 Million From Roslyn Schools

Frank Tassone, the superintendent of the Roslyn Union Free School District on Long Island, led what remains the largest embezzlement from a public school system in United States history, stealing along with a small ring of district insiders more than $11 million between the mid-1990s and 2004. He pleaded guilty to grand larceny in 2005, was sentenced to four to 12 years in prison, and was released for good behavior in 2010. The Roslyn schools embezzlement involving Frank Tassone destroyed the finances of one of the country’s top-ranked school districts and forced statewide changes in how New York audits its schools.

The Superintendent Roslyn Trusted

Roslyn hired Tassone in 1992. Over the next dozen years he built a reputation as an erudite, hands-on leader, introducing values education and community-service requirements and winning the local Rotary Club’s Man of the Year award. Test scores climbed. In April 2004, weeks before his resignation, the Wall Street Journal ranked Roslyn High School the sixth-best public high school in the country.¹

He also presented himself as a widower devoted entirely to his students. He was not. Tassone had been living with his partner Stephen Signorelli in Manhattan for decades and co-owned a house in Las Vegas. The public monk and the private life financed by the district existed side by side for years.¹

How the Money Was Taken

The scheme worked because Tassone had placed allies in the district’s financial and oversight jobs. Bills and checks moved without scrutiny. Expense accounts were padded, bidding rules ignored, check records fabricated, and shell companies invoiced the district for services that did not exist.¹

One shell company, WordPower, collected $800,000 from the district for computer teaching materials. It was registered to Tassone’s Manhattan apartment.² Prosecutors documented more than $1 million in ATM cash advances charged to district accounts, with Tassone averaging about $21,700 in monthly withdrawals between February 2001 and October 2002.³

Assistant superintendent for business Pamela Gluckin ran a parallel operation. She created shell companies with her husband, issued them phantom contracts, and exploited overlaps in the district ledger. School checks written to “Wells Fargo” could plausibly be paying the district’s security vendor of that name, or her personal mortgage lender. A later audit found 74 unauthorized school credit cards circulating among family members and friends of Gluckin and other employees.⁴

What the Stolen Money Paid For

Tassone charged the district for two Concorde flights to London, one costing $20,000 and the other $30,000, and stayed in $1,800-a-night hotel suites. He took gambling trips to Las Vegas on the schools’ dime. Personal expenses billed to Roslyn included rent on an Upper East Side apartment, a Mercedes, jewelry, furniture, skin treatments, weight-loss surgery, and more than $33,000 in dry cleaning.¹ Prosecutors also cataloged roughly $30,000 in household purchases such as toilet paper, pet food, and laundry.⁵

Money also flowed to people close to Tassone. Signorelli, who had no prior business dealings with the schools, received a no-bid $572,000 printing contract over five years and returned $219,000 of it to Tassone.⁶ Tassone transferred another $300,000 into bank accounts held in his sisters’ names.¹

The 2002 Discovery That Went Nowhere

The fraud began to surface in the fall of 2002, when the district’s outside accountant, Andrew Miller, found that Gluckin had stolen $250,000. The first clue was almost trivial: Gluckin’s son, John McCormick, had used a district Home Depot credit card to buy supplies for his private contracting business.²

When Miller reported the findings, Tassone persuaded the school board not to press charges. A public investigation, he argued, would damage the district’s reputation and depress local property values. A district attorney the board hired for advice agreed. Gluckin quietly resigned, kept her administrator’s license, and repaid the initial theft. Tassone told the community she was “gravely ill.” The board also decided not to file a claim under its fidelity bond, a decision that would later prove very expensive.²⁷

How the Cover-Up Broke Open

The silence held for more than a year. In February 2004, anonymous letters reached local politicians and the Nassau County District Attorney’s office. They laid out the 2002 theft and, for the first time in public, accused Tassone himself of stealing.² A formal investigation began.

Around the same time, Rebekah Rombom, co-editor of the Roslyn High School student newspaper The Hilltop Beacon, received tips and published a story on the allegations. Her article did not name Gluckin, at the request of school officials, and drew a muted immediate reaction, but it prompted Newsday and other professional outlets to start pulling on the district’s financial records.⁸⁹

The moment that connected Tassone directly to the fraud came on June 1, 2004, when the new assistant superintendent, Anthony Annunziato, ran down the WordPower invoices and matched the company’s address to Tassone’s apartment. Tassone resigned on June 10, 2004, and was arrested on July 6.¹

The $11 Million Total

In early 2005, New York State Comptroller Alan Hevesi issued an audit titled “Anatomy of a Scandal” that put the total loss above $11 million and grouped it by category:

Nearly $6 million in personal credit card charges and cash withdrawals, across cards held by at least 13 people.
More than $1 million in private mortgages and loans.
More than $1.3 million funneled to sham businesses run by district officials, relatives, and friends.
More than $549,000 in inflated salary and benefits to certain officials.
More than $1.3 million for automobiles, computers, food, postage, and travel treated as personal assets.

The comptroller concluded that Tassone and Gluckin were able to override the district’s accounting system and push payments through outside normal channels, while internal controls had collapsed.¹⁰ A separate review found the district’s external auditing firm, Miller, Lilly & Pearce, had done work Hevesi called “appallingly inadequate,” and he referred the findings to prosecutors and to the State Board for Public Accountancy.¹¹

Who Was Charged and What They Got

Six people were charged in the case. Four were district employees.¹²

Frank Tassone pleaded guilty to first- and second-degree grand larceny in September 2005, admitting to stealing more than $2 million.³ He was ordered to pay roughly $2 million in restitution and cooperate with the investigation. After he repeatedly failed to appear for sentencing, he was arrested and jailed. On October 10, 2006, Acting Nassau County Supreme Court Justice Alan Honorof sentenced him to four to 12 years in prison.¹³ Tassone told the court, “I am deeply sorry to the people of Roslyn, to the youngsters of Roslyn. I am sincerely sorry for what I have done.” Judge Honorof answered, “Today you are a traitor and have committed treason against our community and our society.”⁵

Pamela Gluckin pleaded guilty in November 2005 to first-degree grand larceny, admitting to stealing $4.3 million, the single largest share of the total. She was sentenced in September 2006 to three to nine years and released in May 2011, having repaid about half of the funds and pledged half her state pension toward the rest. She died in 2017.¹²

Stephen Signorelli, Tassone’s partner, pleaded guilty to grand larceny over the no-bid printing contract and was sentenced to one to three years in March 2006.⁶

Debra Rigano, a former account clerk, pleaded guilty in November 2005 to second-degree grand larceny and was sentenced in September 2006 to two to six years, with $852,000 in restitution.¹⁴

Andrew Miller, the district’s independent auditor, pleaded guilty to a felony charge of tampering with public records, admitting he had altered district records at Tassone’s request to hide the theft.¹⁵

John McCormick, Gluckin’s son, was initially charged with grand larceny for using a district Home Depot credit card for his contracting business and later pleaded guilty to grand larceny tied to more than $80,000 in building materials.¹⁶¹⁷

The Insurance the District Never Collected

When the board declined to report Gluckin’s 2002 theft, it also chose not to notify its insurers. Roslyn carried a $1 million fidelity bond, two $1 million errors-and-omissions policies, and a $25 million excess catastrophe policy. Once the full scope of the fraud emerged, the insurers disclaimed coverage, citing the district’s failure to give timely notice.¹⁸

The district sued its former general counsel, Jaspan Schlesinger Hoffman LLP, for legal malpractice, alleging the firm had advised the board it was not obligated to report the theft to law enforcement or insurers. A Nassau County court allowed the malpractice claim to proceed and dismissed a separate breach-of-fiduciary-duty claim.¹⁸

What Changed in New York Schools

In July 2005, the governor signed legislation the comptroller’s office called the “Five Steps to Financial Accountability” for New York school districts:

Six hours of mandatory financial oversight training for every school board member.
An internal audit function in each district.
Board audit committees responsible for selecting external auditors and reviewing financial reports.
Competitive bidding for external auditing services.
Formal board responses whenever an audit raises questions.

The comptroller’s office received $5.8 million in additional annual funding to hire 84 new auditors, with the goal of auditing all 700 school districts in the state within five years.¹⁹ Individual districts separated financial duties so no single employee could control every step of a transaction and brought in external claims auditors reporting directly to the school board.²⁰

The Pension That Kept Paying

After his conviction, Tassone continued to draw a New York State pension of $173,495 a year. Gluckin drew $54,998 annually while in prison. The state constitution provides that public employee retirement benefits cannot be diminished or taken away, even after a felony conviction, and unlike Illinois, Georgia, Pennsylvania, and Texas, New York has no statute requiring pension forfeiture for convicted public officials.²¹

Bills to allow forfeiture, including proposed constitutional amendments, have been introduced repeatedly and consistently stalled, largely because of opposition from public employee unions. As of the most recent reporting, reform bills remained in committee.²¹

Where Tassone Is Now

Tassone was released from prison on February 2, 2010, after roughly three and a half years, on early release for good behavior.²²²³²⁴

1
New York Magazine. The Bad Superintendent
2
Newsday. Bad Education True Story
3
CBS News. Ex-Schools Chief: I Stole Millions
4
The New York Times. A Suspicious Clerk and a School Scandal
5
New York Post. Jail for Traitor
6
The New York Times. Companion of Roslyn Schools Chief Is Sentenced
7
The New York Times. Failure to File Timely Insurance Claim May Cost Plundered School
8
The New York Times. On Top of the News at Roslyn High
9
Yahoo Entertainment. Bad Education Fact Check
10
New York State Comptroller. Anatomy of a Scandal
11
Education Week. N.Y. Comptroller’s Report Blasts School Audit Firm
12
Newsday. Ex-Roslyn School Official Out of Prison
13
The New York Times. Former Roslyn Superintendent Sentenced
14
New York Daily News. Ex-School Clerk Gets 2-6 Yrs for Theft
15
The New York Times. Auditor Admits He Falsified Roslyn Records
16
WNYC. Sixth Charged in for Stealing From Roslyn Schools
17
The New York Times. Contractor Pleads Guilty to Theft From Roslyn Schools
18
New York State Courts. Roslyn Union Free School District v. Jaspan Schlesinger Hoffman LLP
19
Education Week. In N.Y., Auditors Comb School Districts’ Books
20
LI Herald. Under a Financial Microscope
21
Newsday. Ex-Roslyn School Officials Collect Pensions in Prison
22
Long Island Press. Ex-Roslyn School Official Freed From Prison
23
Oxygen. Where Are Pamela Gluckin and Frank Tassone Now
24
Yahoo. The Real Frank Tassone True Story