A Woodbridge resident has pleaded guilty to tax evasion in federal court. Anthony Delmaro, 48, admitted to a decade-long scheme to avoid paying taxes on earnings from his commercial roofing and paving business, Kings Roofing.
According to the U.S. Attorney for the District of Connecticut, David X. Sullivan, and Thomas Demeo, Acting Special Agent in Charge of IRS Criminal Investigation in New England, Delmaro entered his plea before U.S. District Judge Sarala V. Nagala in Hartford on August 19, 2025.
Court documents show that since at least 2012, Delmaro operated Kings Roofing without registering the business with the Connecticut Secretary of State or obtaining a federal Taxpayer Identification Number. From 2012 through 2022, Kings Roofing received approximately $20.9 million from customers. During this period, Delmaro paid workers in cash and failed to file any income or payroll tax returns for himself or the business.
Authorities said Delmaro cashed customer checks at check cashing businesses rather than depositing them into bank accounts and provided addresses associated with UPS mailboxes instead of his home address when conducting these transactions. The use of UPS mailbox addresses complicated efforts by the IRS to trace the income through Currency Transaction Reports filed by check cashers.
Delmaro also had customers file false Forms 1099 using either a family member’s name or an alias he provided—“Sonny Rubino”—making it more difficult for authorities to track income attribution. In cases where customers demanded a Form W-9 with taxpayer identification information before making payments, Delmaro often supplied forms completed with his father’s name and Social Security number along with a UPS mailbox address. His father used an alias different from the information given to customers.
For tax year 2022 alone, Delmaro cashed $3,710,628 in checks payable to Kings Roofing at check cashing businesses and received $439,700 in business-related deposits into his personal account. He also caused 24 Forms 1099-NEC totaling $1,908,095 to be filed with false information.
The investigation further found that between 2019 and April 2025, Delmaro obtained over $500,000 in Husky Health Low Income Medical benefits—a Medicaid program funded by both federal and state governments and administered by the Connecticut Department of Social Services—while failing to report substantial business income.
Delmaro agreed to pay restitution totaling $1,129,669 to the IRS and $578,259 to the Connecticut Medicaid program.
Judge Nagala set sentencing for December 17. Delmaro was released on a $50,000 bond pending sentencing.
The Internal Revenue Service Criminal Investigation Division led the investigation. Assistant U.S. Attorney Christopher W. Schmeisser is prosecuting the case.
