The owner and operator of an unlicensed prize insurance company who for years avoided paying claims, ignored cease and desist orders and was convicted of illegal sales and theft has pleaded guilty to fraud.
Kevin Kolenda of Norwalk, Conn., pleaded guilty this week in federal district court to wire fraud, according to David X. Sullivan, U.S. Attorney for the District of Connecticut. Kolenda’s jury trial is scheduled to begin Sept. 23. Federal charges against him were filed in April 2024.
During the years that Kolenda engaged in illegal conduct, neither Kolenda nor his entities were licensed to sell insurance products, and many state insurance departments issued cease-and-desist orders to stop him, but Kolenda ignored the warnings. Since 2011, he has been convicted four times in various states for activities related to his insurance business.
According to federal court documents, Kolenda owns and operates Hole-in-Won LLC, Compliance HIW LLC, Hole-in-Won Worldwide and Hole-in-Won.com, which together provide prize insurance to customers who offer promotions or prizes at events such as golf tournaments and fishing derbies. through the website, www.hole-in-won.comIn and other promotional materials, Hole-in-Won claims to be “the world’s most successful prize insurance company” and has “paid out thousands of prizes” to winners around the world.
Grand jury indicts ‘Hole in Won’ owner on bonus insurance fraud charges
However, prosecutors said the investigation revealed that Kolenda had, in fact, defrauded dozens of organizations and individuals out of hundreds of thousands of dollars for years.
In a wire fraud case investigated by the FBI, Kolenda admitted that beginning in 2019 and through at least April 2024, he knowingly deceived Hole-in-Won customers through multiple material misrepresentations to induce them to pay him premiums that he had no intention of claiming for insurance winnings. Such misrepresentations include representations that if there is a winner in an insured event, the winner will pay the total cost of all insured prizes, even if he does not intend to do so in certain circumstances.
As part of the program, clients (usually charities or civic organizations) receive insurance from Kolenda and Hole-in-Won for one or more prizes in an event. For example, the organizer of a golf tournament might offer a reward, such as a new car, to any player who scores a hole-in-one on a specific hole. The customer will pay the insurance premium and if there is a winner in the event, Kolenda and Hole-in-Won will undertake to pay the insurance claim for the cost of the insured prize. If no one wins the insurance prize at the event, Kolenda and Hole-in-Won will keep the premium.
Officials allege that if someone won an insurance bonus, Kolenda would use “a variety of fraudulent tactics to avoid paying the claim.” For example, Kolenda frequently used various aliases to conceal his participation in the program; he referred insured persons to the non-existent Hole-in-Won “claims department” located in the Washington, D.C., office; frequently made excuses for Kong’s delay in paying claims; and threatened insured persons that they would face false legal action and damage their reputations if they continued to pursue claims.
Eventually, officials said, Kolenda would stop responding to victims and refuse to pay for insured prizes. Prosecutors say victim sponsors or organizations or their partners often pay for insured prizes themselves to avoid reputational damage and potential legal action.
One example cited by prosecutors involved the Mount Carmel VFW, a veterans association in Mount Carmel, Pennsylvania. Hole-in-Won agreed to pay Mount Carmel VFW $1 million if a participant makes a hole-in-one on the golf course’s 18th hole during a tournament at Pine Hills Golf Club in Paxinos and $10,000 if a participant makes a putt over 60 feet on the green, all in exchange for a $500 premium. However, Kolenda does not intend to make any such payments.
The federal indictment is not the only time Kolenda has been arrested for illegally selling insurance. Over the years, numerous states issued cease-and-desist orders to stop him. These states include Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California and Arkansas.
In 2011, he was convicted of theft in Connecticut Superior Court and ordered to pay restitution and serve three years of probation. In 2013, he was convicted in Missoula County Court in Montana of one count of being an unlicensed insurance producer and fined $10,000. In 2014, Kolenda was found guilty of two counts of unauthorized insurance transactions and theft in King County Superior Court in Washington and was sentenced to 90 days in jail. In 2016, he was convicted again in King County Superior Court of attempted theft and attempting to engage in unauthorized insurance transactions and was sentenced to 15 months in prison.
Kolenda pleaded guilty in federal court this week to one count of wire fraud, which carries a maximum penalty of 20 years in prison. He is scheduled to be sentenced on December 15. In the plea agreement, Kolenda also agreed to pay restitution.
Kolenda was arrested on April 5, 2024. Prosecutors said that while Callenda was released on bail pending trial, he violated the conditions of his release by continuing to sell prize insurance without a proper license, and his bail was revoked. He has been detained since March 6, 2026.
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