What Actually Tripped the IRS in a Multi-Year Cash Tax Scheme

The roofing jobs looked ordinary. Shingles. Tar. Invoices. Nothing flashy. But for more than a decade, the money trail under Anthony Delmaro’s business had more twists than a bad extension cord. Federal prosecutors eventually followed it anyway. What they found was a textbook example of how old-school cash tricks still land people in very modern trouble.

How the Past Was Built on Cash

Anthony Delmaro, 49, ran a commercial roofing and paving operation in Connecticut, most often under the name Kings Roofing. From 2012 through 2022, the business generated approximately $20.9 million in customer receipts. That number alone raises eyebrows. The rest made jaws tighten. Kings Roofing was not registered with the Connecticut Secretary of State. It had no federal taxpayer identification number. Workers were paid in cash. No income tax returns. No payroll tax filings. No paper trail anyone could rely on. Instead of depositing customer checks into a business account, Delmaro cashed them at check-cashing stores. When those stores filed Currency Transaction Reports, the address attached was not a home or office. It was a UPS mailbox. That meant the IRS saw money moving but had no clean way to connect it back to a person.

When checks were not cashed, they went into Delmaro’s personal bank account. Not a business account. Not a trust account. Just personal. Then came the paperwork shuffle. Customers were told to issue Forms 1099 to family members. Sometimes to Delmaro himself. Sometimes to an alias, “Sonny Rubino.” When customers demanded a W-9 before paying, Delmaro provided one using his father’s name and Social Security number, plus another UPS mailbox address. It was a shell game with forms. Income moved. Names changed. Addresses blurred. The goal was simple. Make attribution painful. For 2022 alone, prosecutors showed Delmaro cashed roughly $3.71 million in checks, deposited another $439,700 into his personal account, and caused 24 Forms 1099-NEC totaling about $1.9 million to be filed with false information. That is not sloppy. That is intentional.

The Present Day Reckoning

The IRS Criminal Investigation Division eventually pieced it together. Cashing patterns. CTR filings. Bank deposits. Mismatched 1099s. False W-9s. It adds up faster than people expect. There was another problem, too. From 2019 through April 2025, Delmaro received more than $500,000 in Husky Health benefits, Connecticut’s Medicaid program. Medicaid eligibility does not play nice with a hidden seven-figure income. That turned a tax case into a broader fraud problem.

In Hartford federal court, U.S. District Judge Sarala V. Nagala sentenced Delmaro to 15 months in prison, followed by two years of supervised release. He was ordered to complete 200 hours of community service. The restitution bill hurt. About $1.13 million to the IRS. Another $578,259 to the Connecticut Medicaid program. Delmaro pleaded guilty on August 19, 2025. He remains free on a $50,000 bond and must report to prison on March 17, 2026. No fireworks. No speech. Just consequences.

How It Was Caught

People love to ask how schemes like this collapse. The answer is rarely cinematic. It is data. CTR filings do not disappear. Check-cashing businesses report activity whether clients like it or not. Banks flag odd deposit behavior. Medicaid audits cross-reference income. Forms 1099 do not quietly forget names and Social Security numbers. The IRS does not sprint. It grinds. As the saying goes, “You can outrun a cop, but you can’t outrun the radio.” In this case, the radio was a decade of financial records. At some point, patterns stop being coincidences.

Lessons for Professionals

This case is not about roofing. It is about controls.

• Cash-heavy businesses are magnets for risk. Paying workers in cash, avoiding payroll filings, and bypassing business accounts is not clever. It is a neon sign.
• Aliases and family names on tax forms are not shields. They are breadcrumbs. Every false 1099 creates another mismatch that can be traced. Every fake W-9 expands the exposure.
• Medicaid and tax compliance overlap more than many realize. Income misrepresentation in one system bleeds into another. That is when penalties stack fast.

For CPAs, bookkeepers, and advisors, the warning is blunt. If a client insists on cash-only operations, refuses registration, or plays games with forms, that is not “entrepreneurial.” That is radioactive. Ask the uncomfortable questions. Document the answers. Walk away if needed. Nobody wants their name anywhere near a case file like this.

Looking Ahead

Delmaro will serve his sentence. The restitution clock will keep ticking. The business model that relied on cash and aliases is done. For the IRS, this case reinforces a boring truth. Paper still matters. Digital tools help, but fraud often unravels because someone could not resist old tricks. For professionals reading this, the takeaway is simple. Compliance is not glamorous, but it is cheaper than prison. Cutting corners might feel slick in the moment, but it usually ends with a very long paper trail and a judge reading numbers out loud. And nobody wants to hear their net worth read back to them that way.