HARTFORD, Conn. — Anthony Delmaro, 49, a Woodbridge roofing contractor and owner of Kings Roofing, was sentenced Wednesday in Hartford federal court to 15 months in prison for tax evasion. His sentence will be followed by two years of supervised release, including 200 hours of community service.
Delmaro operated Kings Roofing and a paving business from 2012 to 2022 without registering the business with the Connecticut Secretary of State or obtaining a federal Taxpayer Identification Number. Prosecutors reported that the business earned approximately $20.9 million in customer receipts during that period.
Instead of properly reporting income, Delmaro paid workers in cash, avoided filing payroll and income taxes, and used elaborate schemes to hide revenue from the IRS. This included cashing checks at multiple check-cashing businesses, using UPS mailbox addresses, filing false Forms 1099, and providing customers with W-9 forms containing aliases or family member information.
For example, in 2022 alone, Delmaro cashed over $3.7 million in checks and deposited $439,700 into his personal bank account, filing 24 fraudulent Forms 1099-NEC totaling over $1.9 million. He also received more than $500,000 in Medicaid benefits from the Husky Health Low-Income Medical Program between 2019 and April 2025.
The judge ordered Delmaro to pay $1,129,699 in restitution to the IRS and $578,259 to the Connecticut Medicaid program. Delmaro pleaded guilty to tax evasion on August 19 and is currently released on a $50,000 bond. He must report to prison on March 17, 2026.
