A Woodbridge roofing contractor pleaded guilty Thursday to evading taxes on more than $20 million in business income over a decade-long scheme that included paying workers in cash, using aliases and cashing customer checks at check-cashing businesses to hide money from federal authorities.
Anthony Delmaro, 48, pleaded guilty to tax evasion before U.S. District Judge Sarala V. Nagala in Hartford federal court. He faces sentencing Dec. 17, and has agreed to pay $1.7 million in restitution to federal and state agencies.
From 2012 to 2022, Delmaro operated Kings Roofing, a commercial roofing and paving business that generated approximately $20.9 million in customer receipts, according to federal prosecutors. Despite the substantial income, he never filed income or payroll tax returns for himself, or his business, and took steps to conceal the operation from the Internal Revenue Service.
Prosecutors said Delmaro cashed customer checks at check-cashing businesses instead of depositing them into bank accounts, providing the businesses with addresses tied to UPS mailboxes rather than his home address to make it difficult for the IRS to trace the income source.
When customers filed required tax forms, Delmaro had them make out Form 1099s to a family member rather than his business. In some cases, he gave customers a Form W-9 completed with his father’s name and Social Security number, along with a UPS mailbox address.
Delmaro also had customers file false Form 1099s made out to a family member, or to his alias “Sonny Rubino,” rather than his business, making income attribution difficult.
In 2022 alone, Delmaro cashed $3.7 million in checks made payable to Kings Roofing at check-cashing businesses and received nearly $440,000 in business-related deposits into his personal bank account. He also caused 24 false Form 1099-NECs totaling more than $1.9 million to be filed with incorrect information.
The investigation also revealed that from 2019 to April 2025, Delmaro fraudulently received more than $500,000 in Husky Health benefits, Connecticut’s Medicaid program for low-income residents.
Kings Roofing was not registered with the Connecticut Secretary of the State until Delmaro learned of the federal investigation, and the business never obtained a federal taxpayer identification number.
Under his plea agreement, Delmaro must pay $1,129,669 in restitution to the IRS and $578,259 to the Connecticut Medicaid program. He was released on a $50,000 bond pending sentencing.
U.S. Attorney David X. Sullivan and Thomas Demeo, acting special agent in charge of IRS Criminal Investigation in New England, announced the guilty plea Thursday.
The case was investigated by the IRS Criminal Investigation Division and is being prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser.
Tax evasion carries a maximum penalty of five years in prison in addition to fines.
