It’s the end of the line for the man behind the Hole in Won company that sold a fraudulent policy for a $10,000 tagged-fish prize offered during Saratoga’s 2018 annual ice fishing derby.
Kevin Kolenda, 69, of Norwalk, Connecticut, pleaded guilty in Bridgeport federal court last week to wire fraud in connection with his operation of a nationwide prize insurance business.
Kolenda was scheduled to face a jury trial this week, but pleaded guilty instead. He will face a sentencing hearing in December and could get 20 years in prison.
Restitution will also be part of the sentencing phase, officials with the U.S. Attorney District of Connecticut confirmed. Specifics on how Saratoga might recoup the money it lost are not yet available, however.
In his plea deal, Kolenda admitted to owning a web of businesses, including Hole in Won LLC, Compliance HIW LLC, Hole in Won Worldwide, and Hole-in-Won.com, which together provided fake prize insurance to customers offering high-dollar, hole-in-one prizes at golf tournaments or, in Saratoga’s case, tagged fish for its derby contest.
The Hole-in-Won website remains operational today and claims to be the “most successful prize insurance company in the world” and to have paid out thousands of awards throughout the world.
But a federal investigation revealed a darker reality. Prosecutors proved that Kolenda defrauded dozens of civic groups and charities, including the Platte Valley Chamber of Commerce, of almost $1 million in fraudulent insurance policies and unpaid claims.
A Web Of Fake Companies
Kolenda wasn’t licensed to sell insurance policies, prompting many state insurance departments to issue cease and desist orders against him over the years.
These include Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California and Arkansas.
Wyoming Insurance Commissioner Jeff Rude told Cowboy State Daily last year that his office maintains a list of licensed insurance salesmen and Kolenda was not part of the state’s database when his company sold its fraudulent policy to the Platte Valley Chamber.
“They would show as 'no company known' in our license database,” Rude said. “And we are also able to pull that information for people if they want to call us.”
A History Of Scams
It’s far from Kolenda’s first brush with the law.
In 2011, he was convicted in Connecticut Superior Court of first-degree larceny and third-degree attempted larceny, resulting in a three-year term of probation and an order to pay restitution.
Two years later, a Montana court convicted him of acting as an insurance producer, fining him $10,000.
His scams caught up with him again in Washington state, where the King County Superior Court convicted him of first-degree theft and unauthorized insurance transactions in 2014, followed by another conviction for attempted theft in 2016, earning him 15 months in prison.
In the latest federal case, Kolenda pleaded guilty to one of six counts of wire fraud. Sentencing is set for Dec. 15.
Fish That Almost Got Away
In Saratoga’s case, Hole-in-Won sold the chamber a policy covering tagged fish prizes worth $5,000, $10,000, and $20,000 during its 2018 fishing derby.
But, when the $10,000 fish was actually caught, it was Kolenda who got away, at least for a time.
Rocky Jones of Arvada, Colorado, received his prize money in June 2018, according to media coverage at the time, with Farm Bureau paying prize money totaling $12,500
According to court documents, Kolenda had a calculated script to avoid paying whenever high-dollar prizes were won.
First he’d tell the client to file a claim with a fictitious Hole in Won Claims Department at a non-existent office in Washington, D.C.
If the victim persisted in pursuing the claim, he would threaten them with legal action and reputational harm.
In time, he would just stop responding altogether, which is exactly what Rude said happened in Saratoga’s case.
Derby Supports Winter Economy
Many of Kolenda’s victims were small, nonprofits using fundraisers to support community events.
Saratoga’s annual fishing derby, on the third weekend of every January, is a vital economic economic push to help fill local restaurants, hotels, and other businesses during a slow time.
In years past, the derby has brought roughly 800 people from several states.
The upcoming 42nd annual Saratoga Ice Fishing Derby, set for Jan. 16-17, features a $2,000 prize for the largest game fish caught, as well as hourly rewards.
Organizers have also added several tagged, “trophy” trout to the lake, worth up to $20,000, $10,000 or $5,000.
Renée Jean can be reached at renee@cowboystatedaily.com.





