Woodbridge Roofing Contractor Gets Prison Term In Tax Evasion Scheme: Feds

A Woodbridge-based roofing contractor was sentenced this week to serve 15 months in prison for tax evasion.

U.S. District Court Judge Sarala V. Nagala imposed the sentence on Anthony Delmaro, 49, of Woodbridge during a proceeding in Hartford Wednesday.

Delmaro will be on supervised release for two years after he serves his sentence. During that time, he must perform 200 hours of community service, according to the U.S. Attorney’s office.

Delmaro pleaded guilty in August. He is currently free on a $50,000 bond, and he must report to federal prison to begin serving his sentence on March 17.

For more than a decade, Delmaro has owned and operated a commercial roofing operation, most frequently doing business as “Kings Roofing.” It also provided paving services, prosecutors said.

Until Delmaro was notified of a federal investigation, Kings Roofing wasn’t registered with the Connecticut Secretary of State’s office, and it did not have a federal Taxpayer Identification Number.

According to the government, from 2012 to 2022, Kings Roofing earned approximately $20.9 million in customer receipts.

Prosecutors said Delmaro took various steps to conceal income and operating expenses from the IRS, such as using aliases, paying workers in cash, and not filing income or payroll tax returns. He also cashed customer checks at various check cashing businesses instead of depositing them in the bank, for example, prosecutors said.

Between 2019 and 2025, Delmaro received medical benefits through a Connecticut Medicaid program for low-income residents, though he wasn’t eligible, according to the government.

Delmaro must pay $1.1 million in restitution to the Internal Revenue Service, plus $578,259 to the Connecticut Medicaid program, prosecutors said.

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Woodbridge Contractor Pleads Guilty To Tax Evasion Scheme: Feds