David X. Sullivan, United States Attorney for the District of Connecticut, and Thomas Demeo, Acting Special Agent in Charge of IRS Criminal Investigation in New England, announced that Anthony Delmaro, 48, of Woodbridge, pleaded guilty to tax evasion before U.S. District Judge Sarala V. Nagala in Hartford on August 19, 2025.
Court documents and statements indicate that since at least 2012, Delmaro owned and operated a commercial roofing business in Connecticut under the name “Kings Roofing,” which also provided paving services. The business was not registered with the Connecticut Secretary of State nor did it have a federal Taxpayer Identification Number until Delmaro was notified of the investigation. Between 2012 and 2022, Kings Roofing earned about $20.9 million in customer receipts. During this period, Delmaro paid workers in cash, did not file income or payroll tax returns for himself or his business, and took measures to hide income and expenses from the IRS.
Delmaro and others involved with his business cashed customer checks at various check cashing businesses rather than depositing them into bank accounts. He supplied check cashers with UPS mailbox addresses instead of his home address. As a result, when Currency Transaction Reports were filed by check cashers, only a UPS mailbox location was available to identify sources of income for the IRS. When he did not use check cashers, Delmaro deposited business-related funds into his personal bank account.
The court also heard that Delmaro asked customers to file false Forms 1099 made out either to a family member or himself rather than the business. Sometimes he gave customers an alias—“Sonny Rubino”—for use on these forms. If customers required a Form W-9 with taxpayer identification information before payment, Delmaro would often provide one filled out with his father’s name and Social Security number as well as a UPS mailbox address; his father used an alias different from what was provided to customers.
For tax year 2022 alone, Delmaro cashed $3,710,628 in checks made payable to Kings Roofing at check cashing businesses and received $439,700 in deposits related to business activity into his personal bank account. He also caused 24 Forms 1099-NEC totaling $1,908,095 to be filed using false information.
Investigators found that between 2019 and April 2025 Delmaro received more than $500,000 in Husky Health Low Income Medical benefits—a Medicaid program jointly funded by federal and state governments and administered by the Connecticut Department of Social Services.
Delmaro agreed to pay restitution amounting to $1,129,669 to the IRS and $578,259 to the Connecticut Medicaid program.
Judge Nagala scheduled sentencing for December 17. Delmaro is currently released on a $50,000 bond pending sentencing.
The Internal Revenue Service Criminal Investigation Division conducted this investigation; Assistant U.S. Attorney Christopher W. Schmeisser is prosecuting the case.
