Grand Jury Indicts ‘Hole in Won’ Owner on Prize Insurance Fraud Charges

April 10, 2024

A federal grand jury in Connecticut returned a six-count indictment charging a Norwalk, Connecticut business owner with fraud offenses related to his operation of a prize insurance business.

According to the officials, Kevin Kolenda owns and operates Hole In Won LLC, which has provided prize insurance to customers offering promotions or prizes at events, including golf tournaments and fishing contests. Hole In Won used a promotional website,, where it claims to be “the most successful prize insurance company in the world” that had “paid out 1000’s of awards” to winners throughout the world.

The indictment alleges that Kolenda has defrauded dozens of organizations and individuals out of nearly $1 million, including approximately $850,000 in insurance premiums paid under false pretenses and more than $100,000 in prize costs that Hole In Won failed to pay.

The charges were brought by Vanessa Roberts Avery, U.S. attorney for Connecticut, and Robert Fuller, special agent with the New Haven division of the Federal Bureau of Investigation (FBI).

An indictment is not evidence of guilt. Charges are only allegations and the defendant is presumed innocent unless and until proven guilty beyond a reasonable doubt.

According to the indictment, as part of the scheme, victims, often charitable or civic organizations, obtained insurance from Kolenda and Hole In Won for one or more prizes at an event. For example, the host of a golf tournament might include a lucrative prize, such as a new car, for any player who hits a hole in one on a specific hole. The victim would complete an insurance contract and pay the insurance premium to Kolenda and Hole In Won, and Kolenda and Hole In Won would promise to pay out the insurance claim for the cost of the insured prize if there was a winner at the event. If no one won the insured prize at the event, Kolenda and Hole In Won would keep the premium.

The indictment further alleges that if someone won the insured prize, Kolenda often used various fraudulent techniques to avoid payment of the claim. For example, Kolenda made excuses to victims as to why Hole In Won did not have to pay out the cost of the claim; referred victims to the Hole In Won “claims department,” at an office in Washington, D.C., which did not exist; and threatened victims with bogus legal action and reputational harm if they continued to seek payment of the claim.

Ultimately, Kolenda would often stop responding to correspondence from victims and refused to pay out the cost of the insured prize and the victim host or organization often paid for the cost of the insured prize themselves in order to avoid reputational harm and potential legal action, prosecutors allege.

The indictment charges Kolenda with six counts of wire fraud, an offense that carries a maximum term of imprisonment of 20 years on each count.

Kolenda appeared on April 5 before U.S. Magistrate Judge S. Dave Vatti in Bridgeport, pleaded not guilty, and was released on a $50,000 bond.

Topics Fraud Connecticut

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