‘Most Successful’ Hole-in-One Prize Insurance Operator Pleads Guilty to Fraud

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 Norwalk, 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.

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

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.

Officials charged that if someone won the insured prize, Kolenda used “various fraudulent techniques to avoid payment of the claim.” For example, Kolenda, often using various aliases to hide his involvement in the scheme, referred insureds to the Hole-in-Won “claims department” at an office in Washington, D.C., which did not exist; made frequent excuses as to why Hole in-Won was delayed in paying the claim; and threatened insureds with bogus legal action and reputational harm if they continued to seek payment of the claim.

Ultimately, officials said, Kolenda would stop responding to the victims and refused to pay out the cost of the insured prizes. 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, according to prosecutors.

One example cited by prosecutors involved the Mount Carmel VFW, a veterans association located in Mount Carmel, Pennsylvania. Hole-in-Won agreed that it would pay $1 million to the Mount Carmel VFW if a participant at a tournament at the Pine Hills Golf Club in Paxinos hit a hole in one on hole 18 of the golf course, and to pay $10,000 if a participant made a 60+ foot putt on the putting green, all in exchange for $500 in premium. Kolenda, however, did not intend to make any such payments.

This federal prosecution is not the only time Kolenda has been caught illegally selling insurance. Over the years, a number of states issued cease and desist orders in an effort to stop him. The states have included Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California, and Arkansas.

In 2011, he was convicted in Connecticut Superior Court of larceny and ordered to pay restitution and serve a three-year term of probation. In 2013, he was convicted in Missoula County Justice Court in Montana of one count of acting as an insurance producer without a license and was fined $10,000. In 2014, Kolenda was convicted in King County Superior Court in Washington of two counts of engaging in an unauthorized insurance transaction and theft and was sentenced to 90 days in prison, and he was again convicted in King County Superior Court in 2016 of attempted theft and attempted engaging in an unauthorized insurance transaction, and was sentenced to 15 months of imprisonment.

In federal court this week, Kolenda pleaded guilty to one count of wire fraud, an offense that carries a maximum term of imprisonment of 20 years. He is scheduled to be sentenced on December 15. In his plea agreement, Kolenda also agreed to pay restitution.

Kolenda was arrested on April 5, 2024. Prosecutors said that while Kalenda was released on bond pending trial, he violated the conditions of his release by continuing to sell prize insurance without an appropriate license to do so, and his bond was revoked. He has been detained since March 6, 2026.