Kevin Kolenda

Introduction

Kevin Kolenda, 69, of Norwalk, Connecticut, pleaded guilty on September 15, 2026, in Bridgeport federal court to one count of wire fraud — an offense carrying a maximum term of 20 years — for operating a fraudulent prize insurance business that for years took premiums from charities, civic organizations, and event hosts and refused to pay legitimate claims . United States Attorney David X. Sullivan’s announcement describes how Kolenda’s companies — Hole-in-Won LLC, Compliance HIW LLC, Hole-in-Won Worldwide, and Hole-in-Won.com — sold prize insurance for golf tournaments and fishing contests while he defrauded dozens of organizations and individuals out of hundreds of thousands of dollars . He was arrested on April 5, 2024, had his bond revoked for continuing to sell prize insurance while on release, and has been detained since March 6, 2026 .

Background Information

Kolenda’s business model was genuine on the collection side and fraudulent on the payout side. Customers offering prizes at events — the classic case being a golf tournament host putting up a new car for any player making a hole in one — completed an insurance contract and paid a premium to Kolenda’s companies, which promised to pay the claim if a winner emerged; if no one won, the companies kept the premium . The Hole-in-Won website claimed to be “the most successful prize insurance company in the world” and to have “paid out 1000’s of awards” to winners around the globe .

When someone actually won an insured prize, the release documents the playbook Kolenda used to avoid paying. Using various aliases to hide his involvement, he referred victims to a Hole-in-Won “claims department” at a Washington, D.C., office that did not exist; made frequent excuses for delayed payouts; and threatened victims with bogus legal action and reputational harm if they kept demanding payment, before simply stopping all correspondence . The victim hosts or their partners often paid the cost of the insured prizes themselves to avoid reputational damage and legal action — meaning charities absorbed the losses his policies were bought to cover .

The Controversy or Incident That Led to Their Cancellation

Pleaded guilty; sentencing pending.

The wire fraud plea on September 15, 2026, is the fifth documented criminal judgment against Kolenda’s prize-insurance selling. During the many years of the conduct, neither Kolenda nor his entities were licensed to sell insurance products, and insurance departments issued cease-and-desist orders in Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California, and Arkansas — warnings the release says he ignored . His prior record includes a 2011 Connecticut Superior Court conviction for first-degree larceny and attempted third-degree larceny with restitution and three years of probation; a 2013 Montana conviction for acting as an insurance producer without a license with a $10,000 fine; a 2014 King County, Washington, conviction on two counts of unauthorized insurance transactions and first-degree theft drawing 90 days in prison; and a 2016 King County conviction for attempted first-degree theft and attempted unauthorized insurance transactions drawing 15 months .

Even the federal case’s pretrial phase documented recidivism: while released on bond pending trial after his April 5, 2024, arrest, Kolenda violated conditions by continuing to sell prize insurance without an appropriate license, and his bond was revoked — he has been detained since March 6, 2026 . The case was investigated by the FBI and prosecuted by Assistant U.S. Attorneys Daniel P. Gordon and Christopher W. Schmeisser .

Public Reaction and Consequences

The release records no public statement from Kolenda; the documented reaction is the long institutional trail — a dozen state insurance departments’ cease-and-desist orders, four prior criminal convictions in three states, and finally an FBI wire fraud prosecution . The consequences are the felony plea with 20 years’ maximum exposure, detention that began in March 2026, and a December 15 sentencing before U.S. District Judge Stefan R. Underhill . The documented victims are charitable and civic organizations — golf tournament and fishing contest hosts who bought insurance against paying a prize, then paid for the prizes themselves when the claims department that did not exist did not pay .

Current Status

Kolenda pleaded guilty on September 15, 2026, and is scheduled to be sentenced by Judge Underhill on December 15 . He has been in federal custody since his bond revocation in March 2026, a detention that followed his documented decision to keep selling unlicensed prize insurance while awaiting trial . The release does not state a sentencing recommendation or restitution figure; the single wire fraud count carries a maximum term of 20 years’ imprisonment .

Impact on Their Career/Life

The plea ends a decades-long record in which Kolenda sold prize insurance nationwide without a license, ignored cease-and-desist orders from a dozen states, and collected four earlier criminal judgments for larceny and unlicensed insurance selling — the federal conviction now being the fifth and the first to carry a potential 20-year term . The Hole-in-Won brands he built the marketing claims around are named in the federal case record as instruments of the fraud, and the nonexistent Washington, D.C., claims department that victims were referred to now exists only in the court record describing it . For the organizations that paid his premiums and then his prizes, the case documents the exact sequence — premium collected, claim dodged, threats made, correspondence dropped — that the December 15 sentence will price .

Sources

• U.S. Attorney’s Office, District of Connecticut, “Operator of Fraudulent Prize Insurance Business Pleads Guilty”, September 15, 2026 — source