Fake Insurance, Real Losses: Prize Scheme Operator Pleads Guilty

• A Connecticut businessman has admitted running an unlicensed prize-insurance operation that defrauded dozens of organisations and individuals, exposing how weak licensing controls and ignored regulatory warnings allowed the scheme to continue for years.

Kevin Kolenda, 69, of Norwalk, pleaded guilty to wire fraud in federal court after prosecutors said he used several companies operating under the Hole-in-Won name to sell prize insurance to organisers of golf tournaments, fishing contests and other events.

Customers paid premiums to insure prizes such as cars that would be awarded if participants achieved specified results. When nobody won, Kolenda and his businesses kept the premiums. But when a participant won an insured prize, prosecutors said Kolenda used various methods to avoid paying the claim.

According to court documents, victims were directed to a supposed claims department in Washington, DC that did not exist. Kolenda allegedly used aliases, offered repeated excuses for payment delays and threatened some victims with bogus legal action or reputational damage. Some organisations ultimately paid prize costs themselves to protect their reputations.

The compliance failures extended beyond the alleged fraud itself. Kolenda and his companies were never licensed to sell insurance products, while insurance regulators in multiple states issued cease-and-desist orders against the operation. The orders were issued in Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California and Arkansas.

Kolenda also had previous convictions for theft and unauthorised insurance activity. He was arrested in April 2024 and, while on bond, allegedly continued selling prize insurance without the required licence. His bond was revoked and he has been detained since March 2026.

He faces a maximum sentence of 20 years for wire fraud and is scheduled to be sentenced on December 15, 2026.