HARTFORD, Conn. — A Connecticut roofing contractor has admitted to a decade-long tax evasion scheme in which he failed to report nearly $21 million in business income, according to federal prosecutors.
Anthony Delmaro, 48, of Woodbridge, pleaded guilty Tuesday before U.S. District Judge Sarala V. Nagala to one count of tax evasion. He waived his right to be indicted, the U.S. Attorney’s Office said.
Court documents show Delmaro owned and operated a commercial roofing and paving business under the name Kings Roofing since 2012. Over a 10-year period, investigators say the business brought in $20.9 million in customer receipts — but Delmaro never filed income or payroll tax returns for himself or the company.
Federal officials noted that Kings Roofing wasn’t even registered with the Connecticut Secretary of State and lacked a federal Taxpayer Identification Number until after investigators launched their probe.
According to investigators, Delmaro paid his employees in cash and used multiple methods to conceal his business activities:
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Cashing customer checks at check-cashing outlets rather than depositing them in business accounts.
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Providing UPS mailbox addresses instead of his own when cashing checks, frustrating IRS attempts to trace the funds.
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Depositing business income into his personal bank account.
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Directing customers to file false 1099 forms under aliases, including “Sonny Rubino,” or in the names of relatives.
Court filings also state Delmaro sometimes provided customers with fraudulent W-9 forms, using his father’s name, Social Security number, and mailbox address.
In addition to the tax evasion charges, investigators say Delmaro improperly received more than $500,000 in Husky Health benefits, Connecticut’s Medicaid program, between 2019 and April 2025.
For the 2022 tax year, prosecutors allege Delmaro:
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Cashed more than $3.7 million in business checks.
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Deposited $439,700 in business funds into his personal account.
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Caused nearly $1.9 million in 1099 forms to be filed with false information.
Delmaro has agreed to repay $1,129,669 to the IRS and $578,259 to Connecticut’s Medicaid program. He was released on a $50,000 bond while awaiting sentencing, which is scheduled for December 17.
If convicted, he faces significant prison time along with additional financial penalties.
