John Trasacco steps out of the federal courthouse in Hartford, where he is on trial for wire fraud and a related conspiracy charge. Andrew Brown

A federal judge sentenced John Trasacco, a 51-year-old West Haven native, to eight years in prison for conspiring with former state Democratic lawmaker Michael DiMassa to steal more than $431,000 in taxpayer funds.

The substantial prison term marks the most serious sentence delivered thus far as part of a federal corruption probe that uncovered more than $1.2 million in taxpayer money that was stolen out of West Haven city hall.

Trasacco is one of four people who were charged by federal prosecutors last year for using phony companies and bogus invoices to embezzle money from West Haven’s finance department. The other defendants include DiMassa, his wife and another city employee.

Before handing down the eight-year prison sentence, U.S. District Judge Omar Williams cited the “exceptional circumstances” of the public theft and Trasacco’s earlier crimes, which include trespassing, drug possession, robbery and assault.

Federal prosecutors did not bring up that criminal history during Trasacco’s week-long trial late last year. The prosecutors were also barred at the time from making any reference to organized crime or the mob.

But Williams was allowed to consider Trasacco’s previous criminal conduct during the sentencing hearing.

Federal sentencing guidelines in Trasacco’s case called for a prison sentence between roughly 33 to 41 months, according to court records. But Williams argued that the circumstances in Trasacco’s case called for an even harsher punishment in order to deter other people from partnering with government officials, like DiMassa, to steal large sums of taxpayer money.

“People should be discouraged from conspiring with public officials in the way that you did,” Williams said.

Trasacco’s defense team, who previously asked for a new trial in the case, argued during Monday’s sentencing hearing that Trasacco was a minor player in the overall scheme. And they placed much of the blame on DiMassa, who, as a West Haven employee, had access to the city’s finance department.

Lillian Odongo, one of the public defenders representing Trasacco, said her client was far less “culpable” than DiMassa or John Bernardo, the other city employee who was sentenced to 13 months in prison.

“Mr. Trasacco was not in a position of public trust,” Odongo said.

But Williams sided with the federal prosecutors who argued that Trasacco was a mastermind and prime beneficiary of the scheme.

During the hearing, Assistant U.S. Attorney Raymond Miller acknowledged DiMassa’s role in processing the phony invoices in West Haven city hall.

But Miller said Trasacco was also integral in planning and orchestrating that fraud.

Trasacco initiated the partnership with DiMassa, Miller argued. Trasacco created the fraudulent invoices that were submitted to the city. And he kept most of the proceeds for himself.

Trasacco didn’t have access to the city’s finance department, Miller said, but he absolutely exploited what was going on in West Haven.

“Mr. Trasacco was the architect, and Mr. DiMassa was the means,” Miller argued.

Despite the significant prison sentence, Williams did lessen the amount of restitution that Trasacco will be required to pay back.

The federal judge ordered Trasacco to repay roughly $143,000 to the city of West Haven, despite the fact that Trasacco pocketed and gambled most of the $431,000 that was stolen through his companies.

That means the rest of the money that was stolen from West Haven will need to be repaid by DiMassa, who is scheduled to be sentenced in Hartford later this month.

Williams largely issued that restitution order because he was skeptical that Trasacco will be willing or able to repay anything.

While issuing his order, Williams noted that Trasacco has no legitimate job and has not reported any business or personal income to the federal government in recent years.

According to federal probation officers, Trasacco was recently asked to estimate how much he owes in delinquent taxes. And according to Trasacco’s presentencing report, he replied, “God only knows.”

Unlike the other West Haven defendants who have been sentenced, Trasacco was immediately handcuffed and marched out of the courtroom by federal marshals.

The defense team had asked that Trasacco get several weeks to sort out his affairs, like the other defendants in the case were.

But Williams argued that Trasacco already had four months to prepare for prison.

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Andrew BrownInvestigative Reporter

Andrew joined CT Mirror as an investigative reporter in July 2021. Prior to moving to Connecticut, Andrew was a reporter at newspapers in North Dakota, West Virginia and most recently South Carolina. He’s covered business, utilities, environmental issues, the opioid crisis, local government and two state legislatures. Do you have a story tip? Reach Andrew at 843-592-9958