The owner and operator of an unlicensed prize insurance company who for years avoided paying claims, ignored cease and desist orders, and has been convicted of illegal sales and theft has pleaded guilty to fraud.
Kevin Kolenda of Norwa
lk, Connecticut this week pleaded guilty to wire fraud in federal district court, according to David X. Sullivan, U.S. Attorney for the District of Connecticut. Kolenda’s jury trial was set to begin on September 23. The federal charges against him were brought in April 2024.
During the years Kolenda engaged in his illegal conduct, neither Kolenda nor his entities were licensed to sell insurance products and a number of state insurance departments issued cease and desist orders in an effort to stop him, warnings that Kolenda ignored. Since 2011, he has been convicted four times in various states for activities related to his insurance operation.
According to documents in federal court, Kolenda has owned and operated Hole-in-Won LLC, Compliance HIW LLC, Hole-in-Won Worldwide, and Hole-in-Won.com, which together provided prize insurance to customers who offered promotions or prizes at events, including golf tournaments and fishing contests. Through the website, www.hole-in-won.com, and other promotional materials, Hole-in-Won claimed to be “the most successful prize insurance company in the world” and to have “paid out 1000’s of awards” to winners throughout the world.
However, prosecutors said an investigation revealed that, in reality, Kolenda had for years defrauded dozens of organizations and individuals out of hundreds of thousands of dollars.
In the wire fraud case that was investigated by the Federal Bureau of Investigation, Kolenda admitted that beginning in 2019 through at least April of 2024, he intentionally defrauded Hole-in-Won customers by making multiple material misrepresentations to induce them to pay him premiums while he had no intention of paying out claims for insured prizes won. Such misrepresentations included representing that Hole-in-Won would pay the total cost of any and all insured prizes if there was a winner at an insured event, even though he did not in certain instances intend to do so.
As part of the scheme, customers, 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 prize, such as a new car, for any player who hits a hole in one on a specific hole. The customer would pay the insurance premium 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.
