Business Blunders

Business Blunders

Catch And Release

Kevin Kolenda kept getting caught selling bogus prize insurance. He never stopped casting for suckers.

Al Lewis's avatar
Al Lewis
Sep 17, 2026
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“Only charlatans have absolute certainty.” – Voltaire


Rocky Jones hooked a trophy trout in the 35th annual Saratoga Ice Fishing Derby in January 2018,

The fish was tagged. He could not detect the color, because he’s color blind, but a friend told him it was purple.

Jones is a veteran ice fisherman, but what were the odds of reeling in a purple tag?

Saratoga Lake is a 300-acre reservoir, roughly 80 miles west of Laramie, Wyo. It is stocked with 10,000 to 15,000 trout each year. And Jones, of Arvada, Colo., caught one of only three with a purple tag.

This made him the improbable winner of a sizable cash prize.

More improbable was the expectation that the company that insured this prize would actally pay.

It was a dubious outfit called “Hole-in-Won,” owned and operated by Kevin Kolenda, 69, of Norwalk, Conn.

Bite me. (Comic: ChatGPT)

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Kolenda has spent more than a decade pretending to insure contests for organizations like the Saratoga/Platte Valley Chamber of Commerce through his Hole-in-Won companies.

His promotional collateral touted “the most successful prize insurance company in the world.” He claimed to have paid out thousands of awards to winners around the world.

Yet whenever his customers tried to collect, he referred them to his “claims department” in Washington D.C., which did not exist. Or he deployed any number of other annoying stall tactics.

There was always another sucker to take his bait – hook, line an sinker.

Over the years, Kolenda and his businesses were hit with cease-and-desist orders, civil judgments and other legal actions in Connecticut, Iowa, North Carolina, Washington, Massachusetts, Oregon, Nevada, Virginia, Minnesota, Pennsylvania, California, and Arkansas. He often dodged those claims as well.

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Here’s a peek at his rap sheet:

  • In 2011, Connecticut Superior Court convicted Kolenda of larceny and ordered to pay restitution and serve three-years of probation.

  • In 2013, a Missoula County Justice Court in Montana convicted him of acting as an insurance producer without a license and fined him $10,000.

  • In 2014, a King County Superior Court in Washington convicted him of engaging in an unauthorized insurance transaction and one count of theft and sentenced him to 90 days in prison.

  • In 2016, the King County Superior Court convicted him again. This time for attempted theft and attempting to engage in an unauthorized insurance transaction. This time he was sentenced to 15 months in prison.

  • In 2024, he was arrested again. While out on bond pending trial, he continued to sell prize insurance without a license. His bond was revoked. And he has been detained since March 6.

On Tuesday, Kolenda pleaded guilty to fraud, after prosecutors alleged he defrauded dozens of organizations and individuals out of hundreds of thousands of dollars. He now faces up to 20 years in prison when he is scheduled for sentencing on Dec. 15.

He’s like a dumb-ass fish that keeps getting caught and released. Didn’t anyone notice his tags?

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