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John Bernardo, one of four defendants accused of stealing hundreds of thousands of dollars from the city of West Haven, pleaded guilty to a federal conspiracy charge on Tuesday.

The guilty plea came more than seven months after federal authorities arrested Bernardo and accused him of helping to form a shell company that submitted more than $636,000 in fraudulent invoices to the local government in West Haven, a city of roughly 55,000 people.

Bernardo, who previously worked for West Haven as a housing specialist, is the first person to plead guilty as a result of the federal investigation, which has exposed serious oversight problems within the city’s finance department.

The charge leveled against Bernardo, 66, is directly tied to Michael DiMassa, a former state Democratic lawmaker and former assistant to the West Haven City Council.

The two men partnered in January 2021 to form Compass Investment Group LLC, the alleged shell company, and federal prosecutors said both men were signatories on the bank account where 13 checks from the city were eventually deposited.

Those checks, according to federal prosecutors, were paid out by West Haven’s finance department, even though no services were ever provided to the city or its residents. All of the invoices that were submitted to the city were approved, in part, by DiMassa, who is currently awaiting a trial set for September.

The conspiracy charge that Bernardo pleaded guilty to can carry a maximum prison sentence of up to 30 years, but Bernardo is likely to face a far lesser sentence due to his guilty plea.

The documents that Bernardo signed with the U.S. Attorney’s Office do not mention any type of cooperation agreement, which could require him to provide assistance to federal prosecutors in the cases involving the other West Haven defendants.

Offhand comments from the defendant

Plea hearings are often scripted affairs, with defendants answering yes or no questions from the judge. But Bernardo spoke off the cuff during his hearing on Tuesday, and he used the opportunity in federal court to try to downplay his role in the alleged conspiracy.

The federal prosecutors claimed during the hearing that they could prove at trial that Bernardo received money out of the Compass Investment Group bank account, including payments that were allegedly disguised as paychecks and retirement payments.

Even so, Bernardo told the federal judge that he was not aware of every aspect of the financial scheme that federal prosecutors accused him and DiMassa of orchestrating.

He specifically said that he was unaware of how much money was being placed into the Compass Investment Group bank account, even though federal prosecutors pointed out that the bank statements were sent to his home in West Haven.

“I didn’t know what the hell was going on until the shit hit the fan,” Bernardo said

The offhand comments that Bernardo made during the plea hearing prompted the lawyers with the U.S. Attorney’s office to ask for clarification at several points to make sure that Bernardo understood and agreed with the charges that he was pleading guilty to.

Bernardo’s defense attorney told the judge that his client was concerned about how much restitution he will be required to pay as a result of his involvement in the scheme.

The final amount that Bernardo will be required to repay will be decided at his sentencing hearing.

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