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 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 revealed that since at least 2012, Delmaro operated commercial roofing businesses in Connecticut under the name “Kings Roofing,” which also offered paving services. Kings Roofing was not registered with the state nor did it have a federal Taxpayer Identification Number until Delmaro was notified of the investigation. Between 2012 and 2022, Kings Roofing received about $20.9 million from customers; however, Delmaro paid employees in cash and failed to file income or payroll tax returns for himself or his business.
Delmaro used several methods to hide income and expenses from the IRS. He and others cashed customer checks at check cashing businesses rather than depositing them into bank accounts. When using these services, he provided UPS mailbox addresses instead of his home address so that Currency Transaction Reports filed by check cashers would list only those mailboxes as contact information. In cases where he did not use a check casher, he deposited business funds into his personal account.
To further complicate income tracking, Delmaro had customers submit false Forms 1099 to a family member or to himself directly instead of his business. Sometimes he gave clients an alias—“Sonny Rubino”—for filing purposes. If required to provide a Form W-9 with taxpayer identification details, Delmaro would often supply one filled out with his father’s name and Social Security number along with a UPS mailbox address; his father used an alias different from what was provided to customers.
In 2022 alone, Delmaro cashed $3,710,628 in checks payable to Kings Roofing at check cashing outlets and received $439,700 in related deposits into his personal account. He also caused 24 Forms 1099-NEC totaling $1,908,095 to be submitted with false data.
Investigators found that between 2019 and April 2025 Delmaro obtained over $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 has agreed to pay restitution totaling $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 while awaiting sentencing.
The Internal Revenue Service’s Criminal Investigation Division conducted the investigation. Assistant U.S. Attorney Christopher W. Schmeisser is prosecuting the case.
