News
February 14, 2026

Mass. Contractor Pleads Guilty in Tax Fraud

Construction Owners Editorial Team

SPRINGFIELD, Mass. (WWLP) – The longtime owner of a Berkshire County construction business has admitted his role in a years-long tax fraud scheme that authorities say deprived federal and state governments of hundreds of thousands of dollars in revenue.

Courtesy: Photo by Markus Winkler on Unsplash

Charging documents state that 76-year-old Dennis Condron of Cheshire, owner of D Condron Construction in Lanesborough, concealed more than $500,000 in customer payments between 2021 and 2024. Investigators allege he cashed client checks rather than depositing them through normal business accounts, diverting the money for personal use and keeping it off official financial records.

How Investigators Say the Scheme Worked

According to prosecutors, Condron routinely withheld information from the professional who prepared his annual tax filings. By failing to disclose the checks he was cashing and diverting, his company’s tax returns underreported gross receipts by hundreds of thousands of dollars, allowing him to avoid significant income tax obligations.

Authorities say the practice continued for at least three consecutive years, creating a pattern that ultimately triggered a financial investigation. The unreported funds, which should have gone toward federal and Massachusetts income taxes, were instead retained by Condron.

The case comes as state officials continue to highlight financial crimes across Massachusetts. A recent unrelated review found over $11 million in public assistance fraud, underscoring the broader focus on accountability and misuse of funds.

Guilty Plea and Upcoming Sentencing

On Tuesday, Condron appeared in court and pleaded guilty to four counts of tax fraud. The charges carry the possibility of prison time, fines, and restitution to both state and federal authorities. A sentencing hearing has been scheduled for May 19th, where a judge will determine the penalties.

Legal analysts note that tax fraud cases involving small, privately owned construction firms are not uncommon, particularly where large volumes of payments are made by check. Cashing checks instead of depositing them into business accounts can make income harder to trace, but modern auditing tools often expose discrepancies.

D Condron Construction has operated in Berkshire County for decades, performing residential and commercial contracting work. It is unclear how the guilty plea will affect the future of the company or its existing contracts.

WWLP-22News will continue to follow the case as sentencing approaches.

Originally reported by Ashley Shook in WWLP.

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