A Woodbridge man who has owned a roofing company in the state for more than a decade has been sentenced to 15 months in prison for a tax evasion scheme.
Anthony Delmaro, 49, faced sentencing on Wednesday in federal court in Hartford, where U.S. District Judge Sarala V. Nagala ordered that his prison term be followed by two years of supervised release, according to the U.S. Attorney’s Office for the District of Connecticut. He was also ordered to perform 200 hours of community service while on release.
According to federal officials, Delmaro, since at least 2012, has owned and operated a commercial roofing business in Connecticut. He most frequently does business as “Kings Roofing,” which also provided paving services, officials said.
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, officials said. Between 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 authorities.
As part of the scheme, Delmaro and others associated with his business allegedly cashed checks from customers at various check cashing businesses instead of depositing them into bank accounts, officials said. Delmaro provided the check cashers with addresses associated with UPS mailboxes rather than his home address, according to authorities.
When the check cashers filed Currency Transaction Reports, the IRS only had a UPS mailbox location to try to identify source of income, officials said. When not using a check casher, Delmaro made business-related deposits into his personal bank account, authorities said.
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, federal authorities said. He would sometimes provide customers with an alias, “Sonny Rubino,” which they used on the 1099, officials said.
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, authorities allege. Delmaro’s father allegedly used an alias, which differed from the name and information Delmaro provided to the customer, according to officials.
In the 2022 tax year, Delmaro reportedly cashed about $3.7 million 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 about $1.9 million to be filed with false information, authorities said.
The investigation allegedly also found that, from 2019 to April 2025, Delmaro received more than $500,000 in Husky Health Low Income Medical benefits, officials said.
As part of his sentencing, Delmaro has been ordered to pay about $1.1 million of restitution to the IRS and $578,259 to the Connecticut Medicaid program.
The sentencing came after Delmaro pleaded guilty in August. He is free on $50,000 bond and is required to report to prison on March 17.