Kevin W. Kolenda, president and chief executive of Hole-In-Won.com, pleaded guilty in Justice Court in Missoula and agreed to pay the winner $10,000, The Missoulian reported Friday.
Kolenda's company sells "insurance" to companies that hold hole-in-one contests, and pays prize money to the winners.
Troy Peissig won such a competition in 2010 at the Missoula Country Club sponsored by Allegiance Life and Health Insurance, but Hole-In-Won.com never paid him the $18,000 prize money.
Kolenda's company claimed the distance from the tee to the hole was only 130 yards, shorter than the required 165 yards set out in the contract.
Witnesses and satellite photographs confirmed the distance was at least 165 yards.
Investigators with Montana's insurance commissioner found Kolenda had come under "repeated regulatory discipline" for fraudulent activities in nine states from Massachusetts, to Texas, to Washington state.
A felony charge of insurance fraud was dropped against Kolenda as part of a plea agreement. He pleaded guilty to a misdemeanor charge and agreed to pay a portion of Peissig's prize money.
Kolenda was given a six-month suspended jail sentence and ordered to pay an additional $185 in court fees.