In 1995, Kolenda founded Golf Marketing while working out of a home his parents owned in Norwalk, Connecticut. Since its humble beginnings, the business' name has changed several times, including: Golf Marketing Worldwide LLC, Golf Marketing Inc., Hole-in-Won.com, and currently Hole-in-Won.com Worldwide. Unfortunately for some contestants, however, Kolenda's game remained the same: cheating them out of winnings.

On Oct. 4, Kolenda pleaded guilty in a Washington court to one count of first-degree theft and two counts of selling insurance without a license. However, Kolenda's legal woes are in some ways just beginning. Having been the subject of investigation over the years in numerous states, he faces similar charges in Montana, Ohio, Georgia, California, New York, Hawaii, Alabama, Massachusetts, Florida, and North Carolina.

The Washington State Office of the Insurance Commissioner (OIC) first issued a cease and desist order against Kolenda in 2004, barring him from “illegal solicitation and transaction of unauthorized insurance,” according to court records. At the time, OIC investigators brought the criminal case to prosecutors. Then in 2009, Connecticut officials fined Kolenda $5.9 million for illegally offering insurance without a license. Authorities would later arrest him in Connecticut in September 2012, subsequently extraditing him to Washington that December.

Kolenda spent about a week in jail prior to posting a $50,000 bond and will likely serve more time. As for charges in Washington for which he pleaded guilty this past Friday, King County prosecutors will recommend the former scammer be sentenced to 3 months in jail, with credit for time already served, provided that Kolenda pays $15,000 in restitution by his Nov. 22 sentencing date. If he fails to pay the $15,000 before sentencing, then prosecutors will recommend he be sentenced to 8 months in jail.

After sentencing, Kolenda will have to pay another $20,000 in restitution, according to the deal. The money will go to two men: $10,000 will be paid to Portland man who organized a golf tournament in Vancouver, Wash., in 2004. He was forced to pay a $10,000 deductible to another insurance carrier when Kolenda, who had sold the man hole-in-one insurance, refused to pay a $50,000 prize to a golfer who scored an ace. A second man, who scored a hole-in-one during a 2010 golf tournament in Snohomish County, will receive the remaining $25,000— the amount of prize money Kolenda reneged on paying after selling insurance to tournament organizers.