Kevin Kolenda: Guilty Plea in Montana Hole-in-Won Wire Fraud Scheme

• Kevin Kolenda, 69, of Connecticut, pleaded guilty to federal wire fraud charges on September 15.
• Kolenda operated Hole-in-Won LLC, providing event prize insurance but consistently failing to pay out prizes.
• His scheme included defrauding the Missoula Country Club in 2010 by not paying an $18,000 hole-in-one prize.
• He was previously charged in Missoula for this incident and ordered to pay $10,000 in restitution.
• Kolenda has an extensive history of similar event prize insurance fraud and regulatory discipline in multiple states.

His method consistently involved collecting insurance premiums for high-value prizes, then refusing to pay out when the insured event occurred.

A Connecticut man, Kevin Kolenda, 69, recently entered a guilty plea on September 15 to federal wire fraud charges in a Connecticut federal court. The charges stem from his long-running scheme involving event prize insurance, which included defrauding entities such as the Montana Chamber Foundation. Kolenda operated his business, Hole-in-Won LLC, providing insurance policies designed to cover large cash prizes for events like golf tournaments.

His business model involved collecting premiums from event organizers, with the understanding that he would pay out the advertised prize if a specific condition, such as a hole-in-one, was met. However, court documents indicate that Kolenda frequently failed to honor these commitments, pocketing the premiums without disbursing the prize money when due. This pattern of behavior led to the recent federal charges and his subsequent guilty plea.

One specific instance of Kolenda's fraudulent activities occurred in 2010, involving the Missoula Country Club in Montana. The club hosted a golf tournament that year, offering a substantial $18,000 prize to any golfer who achieved a hole-in-one. To mitigate their financial risk, the Missoula Country Club purchased prize insurance from Kolenda's Hole-in-Won LLC.

During the tournament, a contestant successfully made a hole-in-one, thereby qualifying for the $18,000 prize. Despite the policy being in place and the condition met, Kolenda never provided the promised funds. This specific failure to pay out led to wire fraud charges being filed against him in Missoula, resulting in an order for him to pay $10,000 in restitution, according to information released by the Montana State Auditors Office.

The recent guilty plea and the Missoula incident are not isolated events but rather part of an extensive history of event prize insurance fraud perpetrated by Kevin Kolenda. Records show that he has faced numerous other cases of regulatory discipline in various states for engaging in the exact same type of conduct. This consistent pattern underscores a deliberate and prolonged effort to defraud event organizers and prize winners.

His method consistently involved collecting insurance premiums for high-value prizes, then refusing to pay out when the insured event occurred. This systemic deception, which continued over many years and across multiple jurisdictions, ultimately culminated in the federal wire fraud charges and his admission of guilt in the Connecticut federal court.

The federal wire fraud charges and Kolenda's guilty plea highlight the serious legal consequences for individuals who exploit niche insurance markets for personal gain. The details of his operations and the specific instances of fraud, including the Missoula Country Club case and the broader scamming against entities like the Montana Chamber Foundation, were brought to light through court documents and official statements from the Montana State Auditors Office.

This case serves as a significant example of regulatory bodies and law enforcement pursuing individuals engaged in such schemes. The conviction reinforces the message that fraudulent activities, particularly those that cross state lines or involve federal communication methods like wire transfers, will be met with rigorous investigation and prosecution, aiming to ensure accountability and deter similar misconduct in the event prize insurance sector.

Compliance officers and legal counsel advising event organizers or insurance brokers should note this case as a cautionary tale regarding due diligence on niche insurance providers, particularly for event prize insurance, to mitigate fraud risks and ensure policy payouts. This conviction highlights the ongoing regulatory scrutiny of such schemes.

Source: Original reporting via Lee Enterprises