GRIMY TIMES EXCLUSIVE: Anthony Delmaro, 48, of Woodbridge, has pleaded guilty to tax evasion, a stunning admission from the owner of Kings Roofing, a commercial roofing and paving business that operated for years without proper registration or taxation. According to U.S. Attorney David X. Sullivan and IRS Special Agent in Charge Thomas Demeo, Delmaro’s shenanigans netted him approximately $20.9 million in unreported income over ten years.
Delmaro, who cashed checks from customers at various check-cashing outlets instead of bank deposits, has agreed to pay nearly $1.2 million in restitution to the IRS and another $578,000 to Connecticut’s Husky Health Medicaid program, which he fraudulently accessed. The investigation revealed that Delmaro received over half a million dollars in medical benefits from 2019 to April 2025 despite his substantial earnings.
The defendant’s tax evasion scheme was sophisticated, involving the use of aliases and false Forms 1099. Customers were directed to use an alias called “Sonny Rubino” on their 1099s, while Delmaro provided them with W-9 forms containing his father’s name and Social Security number.
Delmaro’s fraudulent activities came to light when the IRS discovered that he had cashed $3.7 million in checks at check-cashing businesses in 2022 alone. The investigation was a joint effort between the Internal Revenue Service, Criminal Investigation Division, and the Social Security Administration, Office of the Inspector General.
Assistant U.S. Attorney Christopher W. Schmeisser is prosecuting this case, which is scheduled for sentencing on December 17th. Delmaro remains free on a $50,000 bond pending his fate.
Related Federal Cases
- Fairfield Landscaper Donald Biagi Jr. Cops to Tax Evasion · Connecticut
- Ira Malkin Pleads Guilty to $484K Tax Evasion · Connecticut
- New York Resident Sentenced for ATM Skimming Scheme · Rhode Island
- Michelle Lefaoe Sentenced in $3M Homeowner Fraud Scheme · Connecticut
- Matthew Harwood Admits to $3.9M Stolen Goods Scheme · Connecticut
Key Facts
- State: Connecticut
- Agency: DOJ USAO
- Category: Fraud & Financial Crimes|Public Corruption
- Source: Official Source ↗
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