HARTFORD – A Woodbridge roofing contractor pleaded guilty to tax evasion Tuesday, Aug. 19, and has agreed to pay more than $1 million in restitution to the IRS and nearly $600,000 to the state Medicaid program, according to David Sullivan, U.S. Attorney for the District of Connecticut, and Thomas Demeo, acting special agent in charge of IRS Criminal Investigation in New England.
Anthony Delmaro, 48, of Woodbridge, waived his right to be indicted and pleaded guilty before U.S. District Judge Sarala V. Nagala in Hartford to tax evasion. Delmaro has agreed to pay restitution of $1,129,669 to the IRS, and $578,259 to the Connecticut Medicaid program.
According to court documents and statements made in court, since at least 2012, Delmaro has owned and operated a commercial roofing businesses in Connecticut, most frequently doing business as “Kings Roofing” in Hamden. The business, which has been around since 1976, also provided paving services.
Kings Roofing provides services throughout Fairfield County, including Norwalk, Stratford, and Bridgeport.
Until Delmaro was notified of this investigation, Kings Roofing was not registered with the Connecticut Secretary of the State and did not have a federal taxpayer identification number. From 2012 to 2022, Kings Roofing earned approximately $20.9 million in customer receipts, but Delmaro paid his workers in cash, never filed income or payroll tax returns for himself or the business, and took several steps to conceal income and operating expenses from the IRS, according to court documents.
As part of his tax evasion scheme, Delmaro and others associated with his business cashed checks from customers at various check cashing businesses instead of depositing them into bank accounts. Delmaro provided the check cashers with addresses associated with UPS mailboxes rather than his home address. When the check cashers filed Currency Transaction Reports, the IRS only had a UPS mailbox location to try to identify source of income. When not using a check casher, Delmaro made business-related deposits into his personal bank account.
Delmaro also had customers file false 1099 forms made out to a family member, rather than his business, or made out to Delmaro himself, making income attribution more difficult. Delmaro sometimes provided customers with an alias, “Sonny Rubino,” which they used on the 1099. If a customer refused to pay unless Delmaro provided a Form W-9 identifying his taxpayer identification number and address, Delmaro often provided a W-9 completed with his father’s name and Social Security number and an address associated with a UPS mailbox.
For the 2022 tax year, Delmaro cashed $3,710,628 in checks made payable to Kings Roofing at check cashing businesses, received $439,700 in business-related deposits into his personal bank account, and caused 24 Forms 1099-NEC totaling $1,908,095 to be filed with false information.
The investigation also revealed that from 2019 to April 2025, Delmaro received more than $500,000 in Husky Health Low Income Medical benefits, which is a Medicaid program.
Judge Nagala scheduled sentencing for Dec. 17. Delmaro is released on a $50,000 bond pending sentencing.
