Roofing Contractor Sentenced to 15 Months in Prison for Tax Evasion Scheme

U.S. Attorney’s Office, District of Connecticut

David X. Sullivan, United States Attorney for the District of Connecticut, announced that ANTHONY DELMARO, 49, of Woodbridge, was sentenced today by U.S. District Judge Sarala V. Nagala in Hartford to 15 months of imprisonment and two years of supervised release for tax evasion.  Delmaro is required to perform 200 hours of community service while on supervised release.

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.”  The business also provided paving services.  Until Delmaro was notified of this investigation, Kings Roofing was not registered with the Connecticut Secretary of 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.

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 (“CTRs”), 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 Forms 1099 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.  Delmaro’s father used an alias, which differed from the name and information Delmaro provided to the customer.

As an example, 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.  Husky Health is a Connecticut Medicaid program, jointly funded by the federal government and by the State of Connecticut and administered by the Connecticut Department of Social Services.

Judge Nagala ordered Delmaro to pay restitution of $1,129,669 to the IRS, and $578,259 to the Connecticut Medicaid program.

Delmaro pleaded guilty to the offense on August 19, 2025.

Delmaro, who is released on a $50,000 bond, is required to report to prison on March 17, 2026.

This investigation was conducted by the Internal Revenue Service, Criminal Investigation Division and the Social Security Administration, Office of the Inspector General.  The case was prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser.