Kevin Kolenda’s company, Hole in Won, sold the Platte Valley Chamber of Commerce in Saratoga, Wyoming, a policy in 2018 to cover the $10,000 prize it offers for catching a tagged fish during its annual ice fishing derby.
But, when the fish was caught, it was the insurer who got away, sticking the charity for the large payout.
At least for a little while.
Wyoming Insurance Commissioner Jeff Rude recently spotted a federal case against Kolenda and has connected the dots between Kolenda and the cold fish case in Wyoming.
“This is much bigger than just our little case,” Rude said. “There’s a whole bunch of cases, you know, a million-plus dollars, that just happened to involve one of our entities.”
The indictment, which was entered in April 2024, accuses Kolenda, 66, of Norwalk, Connecticut, of defrauding dozens of organizations and people of nearly $1 million, including $850,000 in insurance premiums paid under false pretenses, and more than $100,000 in unpaid prize money.
In all, Kolenda faces six counts of wire fraud, each with a maximum sentence of up to 20 years.
The case is still under investigation by the FBI’s New Haven Division, and agents are encouraging anyone who may have been a victim of Kolenda and his company to come forward and contact them at 203-777-6311.
Kolenda’s trial has been scheduled for August.
How The Scheme Worked
Kolenda’s scheme, according to the federal indictment issued in Connecticut, worked by selling insurance policies to charitable and civic organizations for eye-catching hole-in-one prizes, like a brand-new car or in Saratoga’s case, tagged fish prizes worth $5,000, $10,000 and $20,000.
Kolenda collected a premium for the insurance policy in exchange for promising he would pay the insured prizes in the event of a winner during the event.
If no one won, Kolenda was to keep the entire premium.
The trouble, according to the indictment, is that Kolenda was keeping premiums regardless of whether there were winners through a variety of strategies, and not paying out on policies when people won.
First, he would tell his clients that they’d have to file a claim with the Hole in Won “Claims Department” at an office in Washington, D.C., which did not exist.
After that, he would threaten legal action and reputational harm to victims seeking payment of a claim.
In time, he would often just stop responding altogether, which is what Rude said happened in Saratoga’s case.
State Helps Spot Insurance Fraudsters
Most of Kolenda’s victims were, similar to the Platte Valley Chamber of Commerce, charity events that were held as fundraisers or other community-oriented events.
Saratoga’s annual ice fishing derby, for example, is part of a community-wide economic push in winter to help support local hotels, restaurants and other businesses during a slow time.
The derby brings around 800 people to the community each year to catch trout and have a good time, filling up hotel rooms and restaurants, and helping local businesses make it through to spring and summer, when there’s more tourism.
Cowboy State Daily reached out to the Platte Valley Chamber of Commerce for a reaction to the indictment against Kolenda, but did not get a response by publication. The policy for the event was written by Farm Bureau in Saratoga. A representative of the business refused to comment.
Rude said that while the Saratoga case is “small potatoes” compared to some of the crimes Kolenda is accused of committing, it was still a big deal for Saratoga at the time, which found itself “on the hook” for a $10,000 prize it had thought would be covered by insurance.
Rude said he doesn’t know of any other cases in Wyoming involving Kolenda, but he hopes the case can raise awareness that his office does keep a list of licensed insurers — which Kolenda was not part of at the time.
“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.”
Renée Jean can be reached at renee@cowboystatedaily.com.
