Norwalk prize insurance businessman pleads guilty to defrauding dozens of organizations

Sep. 15—BRIDGEPORT — A Norwalk resident who operated a prize insurance business pleaded guilty to wire fraud Tuesday after he was accused of defrauding dozens of organizations and individuals, federal prosecutors said.

Kevin Kolenda, 69, entered the plea during a hearing in Bridgeport federal court, according to a news release shared by U.S. Attorney for the District of Connecticut David X. Sullivan.

Sullivan said Kolenda owned and operated the prize insurance business Hole-In-Won LLC., which has provided prize insurance to clients who offered promotions at events such as golf tournaments.

As an example, officials said an organizer of a golf tournament would enter a contract with Kolenda's company, who would promise to pay the insurance claim for the cost of an insured prize if there was a winner at an event.

The investigation revealed that Kolenda defrauded dozens of clients, often charitable or civic organizations, out of hundreds of thousands of dollars by simply not paying out the insurance claims, Sullivan said.

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Sullivan said Kolenda used various aliases to hide his involvement in the scheme, referred victims to a nonexistent claims department office in Washington, D.C., and threatened victims with bogus legal action if they continued to seek payment.

"Ultimately, Kolenda would simply stop responding to correspondence from victims and refused to pay out the cost of the insured prizes," Sullivan said.

Sullivan said the victim hosts or organizations, or their partners, often paid for the cost of the insured prizes themselves in order to avoid reputational harm and potential legal action.

Sullivan noted that neither Kolenda nor his entities were licensed to sell insurance products. He said multiple states, including Connecticut, instructed him and his businesses to cease and desist from selling prize insurance coverage.

Sullivan said Kolenda was previously convicted of first-degree larceny in Connecticut in 2011, acting as an insurance producer without a license in Montana in 2013, engaging in an unauthorized insurance transaction in Washington in 2014 and engaging in an unauthorized insurance transaction in New York in 2016.

Kolenda was arrested on April 5, 2024, but was later released on bond. He was detained again on March 6 after he violated the conditions of his release by continuing to sell prize insurance without a license, Sullivan said.

Kolenda is scheduled to be sentenced by U.S. District Judge Stefan R. Underhill on Dec. 15. He faces up to 20 years in prison.

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