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Old Saybrook contractor gets 15 months in prison for tax evasion

The longtime owner of Old Saybrook-based construction businesses was sentenced Wednesday to 15 months in federal prison for tax evasion.

U.S. District Court Judge Omar A. Williams imposed the sentence on Dimitrios “Jimmy” Kassimis, 58, of Old Saybrook, in a proceeding in Hartford.

Kassimis remains free on bond, but he must report to the federal Bureau of Prisons to begin serving his sentence on April 24. After Kassimis serves his sentence, he will be on supervised release for three years. He pleaded guilty to the tax charge back in November.

Williams ordered Kassimis to pay any outstanding taxes. The government has estimated that he owes the Internal Revenue Service approximately $233,086. 

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Kassimis said he has a gambling addiction, and he spent a large portion of his earnings gambling at casinos and on personal expenses, court documents show. 

Defense Attorney Jeremiah Donovan of Old Saybrook indicated in a pre-sentencing memorandum that his client is “ashamed.”

“He has hit rock bottom,” Donovan wrote. “He has lost the respect of the community and his family.” 

Assistant U.S. Attorney David T. Huang said the crime was not a momentary lapse in judgment. 

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“He made a series of long-term decisions calculated to benefit himself financially and to avoid his obligation to pay his share of taxes,” Huang said, in a pre-sentencing memorandum.

Kassimis owns construction-related businesses including Allstate Contracting Group and JRC Renovations, both based out of his Old Saybrook home.

According to the U.S. Attorney’s office, between 2018 and 2021 Kassimis did not file any personal or business federal income tax returns, in spite of earning “substantial income.” He also failed to file employment tax returns.

Between 2018 and 2021, Kassimis earned nearly $2.8 million in revenue through Allstate Contracting Group, according to Huang. 

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The IRS’s Criminal Investigation Division determined that Kassimis did not have any personal bank accounts. Kassimis paid his personal expenses through his business bank accounts, and also made cash withdrawals from business accounts, prosecutors said. 

Kassimis also failed to issue required federal tax forms to his employees and sometimes paid them in cash, according to the government.

Contact Michelle Tuccitto Sullo at msullo@newhavenbiz.com.

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