Dennis Condron, 76, of Cheshire, pleaded guilty Tuesday in federal court in Springfield to four counts of tax fraud after prosecutors said he pocketed more than $500,000 in customer checks meant for his Berkshire County construction business. According to court records, Condron ran the scheme through his company, D Condron Construction, and did not report the diverted payments on his federal tax returns. U.S. District Judge Mark G. Mastroianni has scheduled sentencing for May 19, 2026.
Local reporting and timeline
The guilty plea caps a case that started with an August federal charging document and months of work by IRS criminal investigators and prosecutors. Local coverage reports that Condron allegedly cashed checks made out to D Condron Construction, steered the money into personal accounts and then underreported his business gross receipts by “hundreds of thousands of dollars,” according to Boston 25 News. That reporting tracks the case from the initial August filing to this week’s guilty plea in Springfield federal court.
How prosecutors say he concealed the payments
In a press release, the U.S. Attorney's Office, District of Massachusetts said the charging document alleges Condron “hid over half a million dollars in customer checks by cashing them and diverting them to his personal accounts.” Prosecutors say he did not tell his tax preparer about those diverted checks, which caused his federal income tax returns to understate D Condron Construction’s gross receipts. The announcement credits IRS Criminal Investigation agents in Boston and identifies Assistant U.S. Attorney Caroline Merck as handling the case.
What comes next in court
Condron is set to be sentenced on May 19, 2026, before Judge Mastroianni in Springfield, according to court notices and federal prosecutors. The U.S. Attorney’s Springfield office is prosecuting the case and says the conduct unfolded over a roughly three-year period, per Western Mass News. Sentencing will factor in the scope of the alleged tax loss and other circumstances in the case.
Pattern in the region
Federal enforcement against contractor tax schemes has surfaced elsewhere in Massachusetts in recent years. For example, a Billerica paving company owner pleaded guilty after authorities said he cashed millions in customer checks and failed to report the income, a case documented by Hoodline. Cases like these highlight the kinds of bookkeeping shortcuts that tend to attract IRS Criminal Investigation attention.
Legal notes
Condron’s sentence will be determined by the judge under the federal Sentencing Guidelines, which weigh estimated tax loss, criminal history and other aggravating or mitigating factors, according to the U.S. Sentencing Commission. Federal law also sets statutory penalties for tax offenses. For example, 26 U.S.C. § 7201 provides that a person convicted of tax evasion may face fines and up to five years in prison, per the U.S. Code. The U.S. Attorney’s Office has noted that restitution, interest and possible state tax consequences may also follow a conviction, according to its press release.
