Imagine running a successful business, raking in millions, only to end up in federal prison for tax evasion. That's exactly what happened to a Connecticut roofing contractor who failed to pay over $630,000 in taxes and went to great lengths to hide his income. Angelo Delmaro, a 49-year-old from Farmington, was sentenced to eight months behind bars, followed by two years of supervised release and 200 hours of community service. But here's where it gets controversial: despite earning approximately $12.7 million from 2012 to 2022, Delmaro never filed income or payroll tax returns—not for himself, not for his business. And this is the part most people miss: he didn't just forget; he actively concealed his income through a web of deceit, including cash transactions, fake identities, and even involving his own father in the scheme.
Delmaro operated under various business names like 'Value Roofing,' 'Roofing Services of New England,' and 'Roofing Services,' while also offering paving services. However, none of these businesses were registered with the Connecticut Secretary of State, nor did they have a federal Taxpayer Identification Number. Instead of depositing customer checks into bank accounts, Delmaro and his associates cashed them at various businesses, using UPS mailbox addresses to obscure the source of income. This made it nearly impossible for the IRS to trace the funds.
But it doesn't stop there. Delmaro had customers file false Forms 1099 under his family members' names, further complicating income attribution. When customers requested a W-9 form, he provided fake identities like 'Harvey Rubino' or 'Tony Stano,' and even used his father's name and Social Security number on a fraudulent W-9. Is this a case of clever entrepreneurship gone wrong, or a blatant disregard for the law? Let’s discuss in the comments.
The scheme unraveled after Delmaro accepted a plea bargain in September, leading to his sentencing in federal court in Hartford. U.S. District Judge Sarala V. Nagala also ordered him to pay $630,869 in restitution to the IRS. This case raises important questions about accountability and the lengths some will go to avoid paying taxes. What do you think—was the sentence fair, or should there be harsher penalties for such actions? Share your thoughts below!
