Wednesday, September 16th, 2026 — A Connecticut man who operated several prize insurance businesses pleaded guilty to wire fraud after federal prosecutors said he collected premiums from organizations and then avoided paying claims when contestants won insured prizes.

Kevin Kolenda, 69, of Norwalk, pleaded guilty Sept. 15 in federal court in Bridgeport. Kolenda operated Hole-in-Won LLC, Compliance HIW LLC, Hole-in-Won Worldwide and Hole-in-Won.com, collectively referred to by prosecutors as Hole-in-Won.

The businesses sold coverage for prizes offered at events such as golf tournaments and fishing contests. An event organizer, for example, could pay a premium to insure the cost of a vehicle offered to a golfer who made a hole in one on a designated hole. If nobody won, Hole-in-Won kept the premium. If a participant won, the company was supposed to cover the insured prize.

Federal investigators found that Kolenda instead defrauded dozens of organizations and individuals of hundreds of thousands of dollars over a period of years. Victims frequently included charitable and civic organizations.

Prosecutors said Kolenda employed several methods to avoid paying claims. He used aliases, directed customers to a purported Hole-in-Won claims department at a Washington, D.C., office that did not exist, offered repeated excuses for delayed payments and threatened customers with bogus legal action and reputational harm if they continued pursuing their claims. He eventually stopped responding to some victims and refused to pay for the prizes.

Event hosts, organizations or their partners sometimes paid for the prizes themselves to avoid legal disputes or damage to their reputations, according to prosecutors.

The case also involved repeated insurance licensing violations. Neither Kolenda nor his entities were licensed to sell insurance products during the years covered by the conduct described by prosecutors. Regulators and courts in multiple states issued cease-and-desist orders, judgments or other legal directives aimed at stopping the sale of the coverage.

Kolenda had previous state convictions involving insurance and theft-related conduct. Connecticut authorities convicted him of larceny and attempted larceny in 2011. A Montana court convicted him in 2013 of acting as an insurance producer without a license. Washington convictions followed in 2014 and 2016 for offenses involving unauthorized insurance transactions and theft or attempted theft.

Kolenda was arrested in April 2024. While released on bond, prosecutors said he continued selling prize insurance without the required license, among other violations of his release conditions. His bond was revoked, and he has been detained since March 6, 2026.

The wire fraud charge carries a maximum prison term of 20 years. U.S. District Judge Stefan R. Underhill is scheduled to sentence Kolenda on Dec. 15.

For claims professionals, the prosecution illustrates how fraud can extend beyond a false claim submitted by an insured. Here, prosecutors described a business that accepted premiums and created the appearance of a claims operation while avoiding payment after covered prize events occurred. The case also shows the potential consequences for insured organizations when promised coverage fails: some ultimately absorbed the prize costs themselves.

The FBI investigated the case. Assistant U.S. Attorneys Daniel P. Gordon and Christopher W. Schmeisser are prosecuting it.