David X. Sullivan, United States Attorney for the District of Connecticut, announced that KEVIN KOLENDA, 69, of Norwalk, pleaded guilty today in Bridgeport federal court to an offense related to his operation of a fraudulent prize insurance business.

According to court documents and statements made in court, Kolenda has owned and operated Hole-in-Won LLC, Compliance HIW LLC, Hole-in-Won Worldwide, and Hole-in-Won.com (“Hole-in-Won”), which together have provided prize insurance to customers who offered promotions or prizes at events, including golf tournaments and fishing contests.  Through its 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.

The investigation revealed that, in reality, Kolenda had for years defrauded dozens of organizations and individuals out of hundreds of thousands of dollars.  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.

If someone won the insured prize, however, 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 victims to the Hole-in-Won “claims department” at an office in Washington, D.C., which did not exist; made frequent excuses to victims as to why Hole in-Won was delayed in paying out the claim; and threatened victims with bogus legal action and reputational harm if they continued to seek payment of the claim.  Ultimately, Kolenda would simply stop responding to correspondence from 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.

During the many years Kolenda engaged in his illegal conduct, neither Kolenda nor his entities were licensed to sell insurance products, and, in many states, insurance departments issued cease and desist orders in an effort to stop his illegal sales, warnings that Kolenda ignored. In fact, Kolenda and his businesses have been instructed to cease and desist from selling prize insurance coverage via cease and desist orders, judgments, and other legal documents in 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 in the first degree and attempt to commit larceny in the third degree 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, he was convicted in King County Superior Court in Washington of two counts of engaging in an unauthorized insurance transaction and one count of theft in the first degree and was sentenced to 90 days in prison, and he was again convicted in King County Superior Court in 2016 of attempted theft in the first degree and attempted engaging in an unauthorized insurance transaction, and was sentenced to 15 months of imprisonment.

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 by U.S. District Judge Stefan R. Underhill on December 15.

Kolenda was arrested on April 5, 2024.  While released on bond pending trial, Kolenda violated the conditions of his release by, among other things, 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.

This matter is being investigated by the Federal Bureau of Investigation.  The case is being prosecuted by Assistant U.S. Attorneys Daniel P. Gordon and Christopher W. Schmeisser.

As of November 1,2026 the Wyoming Department of Insurance will no longer accept paper form(s) for the below business entity license related services.

• Voluntary Surrender

• Name Change

• Address Change

Submit these services online through Sircon ↗. Select the Additional State Service Request and then the reason for the request and the required form. This process requires completing a form and attaching it to the request.

There is no charge for this service however, there is a $3.50 processing fee.

Questions concerning these changes may be sent to the licensing section at insurancelicensing@wyo.gov or by phone at (307) 777-7319.

Lisa Hastings, SILA-A
Licensing Supervisor
Lisa.hastings2@wyo.gov

The Department of Insurance received notification from the company that a processing issue with the Allstate Drivewise product has been identified which affects approximately 454 iPhone users in Wyoming.  Routine monitoring and audits by the company revealed that the iPhone application was incorrectly reporting driving events, specifically hard braking and rapid acceleration, in approximately 25% of the audited cases.

In response to these findings, the company has confirmed that refunds of the increased premium resulting from the identified Drivewise product processing issue are being issued to all affected customers. These refunds are anticipated to average $45 including interest, and will begin processing on or about May 7. Impacted customers should receive formal notice from Allstate along with their refund check. The company's technical team has implemented a process to resolve this issue and ensure the future accuracy of their products.