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Michael DiMassa’s affairs, gambling habits in spotlight during trial

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Former state Rep. Michael DiMassa leaves federal court in New Haven on Oct. 20, 2021.

The personal and professional life of Michael DiMassa, a former Connecticut lawmaker and West Haven city employee, was on full display in federal court on Tuesday as lawyers scrutinized his finances, his gambling habits and his “sexual escapades.”

For the second day in a row, DiMassa was placed under oath in federal court in Hartford, where he is serving as the star witness in a jury trial that is examining how hundreds of thousands of dollars were allegedly stolen from West Haven taxpayers.

Federal prosecutors called DiMassa as a witness on Monday in an attempt to prove their case against John Trasacco, a Branford resident who allegedly conspired with DiMassa to steal more than $430,000 from the city.

The line of questioning from the federal prosecutors on Monday largely focused on how DiMassa, who served as an assistant to the West Haven city council, allegedly helped Trasacco to pass off fraudulent invoices within the city.

That all changed on Tuesday, however, when Trasacco’s team of public defense attorneys began questioning DiMassa.

The focus of the trial shifted quickly away from Trasacco’s alleged wrongdoing and, instead, delved into the past actions of DiMassa, who pleaded guilty earlier this month to three related conspiracy charges.

Trasacco’s defense team’s strategy was apparently to impeach DiMassa’s character so jurors would have reason to question his motives and credibility while he is on the witness stand.

The defense team avoided asking DiMassa about how he allegedly processed bogus invoices that were submitted by two companies — JIL Sanitation Solutions and L&H Company — which were formed and controlled by Trasacco.

Instead, the defense attorneys highlighted the other ways that DiMassa embezzled money for his own benefit.

They spent several hours questioning DiMassa about the $636,000 that went to Compass Investment Group LLC, a shell company that he and John Bernardo, another city employee, set up in order to submit fraudulent invoices to the city.

They peppered DiMassa with questions about another $147,000 in fraudulent payments that he approved for Lauren Knox, whom he later married in October 2021. Bernardo and Knox pleaded guilty to conspiracy earlier this year.

And they asked him how many people he took advantage of and how many lies he told in order to steal that amount of money from the city.

“Lying just comes very naturally to you?” Lillian Odongo, one of the public defenders, asked DiMassa during the trial.

“At that point in time, that is very safe to say,” he replied.

The defense attorneys also spent hours Tuesday afternoon seeking to paint DiMassa, who was elected three times to the state legislature, as a sexual philanderer and gambling addict who was desperate for money.

To drive home that message, the defense team asked DiMassa about three different women with whom he had relationships between 2020 and 2021 and why all three of those women received checks from the city of West Haven in recent years.

The lawyers went through the three women one by one, and DiMassa acknowledged having sexual relationships with all three of them.

He said he dated Lauren Knox, his current wife, on and off throughout 2020 and 2021 while he was approving fraudulent invoices using her name.

Around the same time, he said, he was also dating Erika Pocock, a former Republican legislative staffer, who received $34,250 from West Haven for supplying face masks, hand sanitizer and “tote bags” to the city, documents show.

And he said he also slept with Kara Rochelle, a state Democratic lawmaker from Ansonia, who was paid $5,000 out of the city’s bank accounts for a consulting services regarding West Haven’s fire stations.

Rochelle did not return a call seeking comment for this story.

From there, the defense team continued questioning DiMassa about his private life, including when he was first introduced to gambling and whether his finances were affected by his trips to casinos and his online sports betting.

DiMassa told the jury that he was first introduced to gambling by his stepfather and that he gambled frequently for years.

That habit, DiMassa admitted, created financial difficulties for him and ultimately contributed to him filing for bankruptcy in 2015.

“I was certainly gambling beyond my means,” DiMassa told the jurors.

“You gambled all your money away?” Odongo said.

“That’s fair to say,” DiMassa replied.

The prosecutors previously portrayed DiMassa as someone who was afraid of Trasacco and was now trying to make amends for his wrongdoing, but the defense attorneys reminded jurors that DiMassa was the lynchpin in the thefts.

The defense team did not attempt to challenge any of the statements that DiMassa made on the witness stand the day before, including the allegation that Trasacco stuffed envelopes of cash into his pocket in return for pushing fraudulent invoices through the city’s finance department.

They did, however, question DiMassa about why he chose to testify against Trasacco and what he hopes to gain by cooperating with federal prosecutors.

DiMassa admitted for the second day that he was hoping to gain a more lenient sentence for testifying. But he rejected insinuations that he was telling the jury what prosecutors wanted him to say.

“I’m here telling the truth,” DiMassa said. “I committed to try to make this right.”

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