Woodbridge, CT– A Connecticut man who owned and operated a commercial roofing business has been sentenced to federal prison after admitting to a decade-long tax evasion scheme that concealed millions of dollars in income.
David X. Sullivan, United States Attorney for the District of Connecticut, announced that Anthony Delmaro, 49, of Woodbridge, was sentenced today by Sarala V. Nagala in Hartford to 15 months of imprisonment followed by two years of supervised release. Delmaro was also ordered to complete 200 hours of community service during his supervised release.
According to court documents and statements made in court, Delmaro has owned and operated a commercial roofing business in Connecticut since at least 2012, most frequently doing business as Kings Roofing, which also provided paving services. Until he was notified of the federal investigation, Kings Roofing was not registered with the Connecticut Secretary of State and did not have a federal Taxpayer Identification Number.
From 2012 through 2022, Kings Roofing generated approximately $20.9 million in customer receipts. Prosecutors said Delmaro paid workers in cash, failed to file income or payroll tax returns for himself or the business, and took deliberate steps to hide income and expenses from the Internal Revenue Service.
As part of the scheme, Delmaro and others associated with the business frequently cashed customer checks at check-cashing businesses instead of depositing them into bank accounts. He provided addresses linked to UPS mailboxes rather than his home address, limiting the IRS’s ability to trace income when Currency Transaction Reports were filed. In other instances, Delmaro deposited business funds directly into his personal bank account.
Investigators also found that Delmaro caused customers to file false Forms 1099, sometimes listing a family member as the payee or attributing income directly to Delmaro instead of the business. In some cases, he used the alias “Sonny Rubino” for reporting purposes. When customers required a completed Form W-9, Delmaro often supplied one using his father’s name and Social Security number along with a UPS mailbox address. His father, prosecutors noted, also used an alias that differed from the information provided to customers.
Court records highlight that in 2022 alone, Delmaro:
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Cashed $3,710,628 in checks made payable to Kings Roofing at check-cashing businesses
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Received $439,700 in business-related deposits into his personal bank account
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Caused 24 Forms 1099-NEC totaling $1,908,095 to be filed with false information
The investigation further revealed that from 2019 through April 2025, Delmaro received more than $500,000 in benefits from Husky Health, Connecticut’s Medicaid program jointly funded by the federal government and the State of Connecticut and administered by the Connecticut Department of Social Services.
Judge Nagala ordered Delmaro to pay $1,129,669 in restitution to the IRS and $578,259 to the Connecticut Medicaid program.
Delmaro pleaded guilty to tax evasion on August 19, 2025. He is currently free on a $50,000 bond and is scheduled to report to prison on March 17, 2026.
The investigation was conducted by the Internal Revenue Service Criminal Investigation and the Social Security Administration Office of the Inspector General. The case was prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser.
