The former owner of defunct online gambling site BetOnSports has lost his bid to reduce his $36m tax bill.

On Wednesday, a three-judge panel of the Eighth Circuit US Court of Appeals rejected Gary Kaplan’s bid to overturn a a $36m back tax and penalties judgment levied against him. BetOnSports shut down in 2006 shortly after CEO David Carruthers was arrested in a Dallas airport during a stopover on his way to Costa Rica, which marked the opening salvo in the US Department of Justice’s crackdown on US-facing online gambling operators.

In 2009, BetOnSports founder Kaplan (pictured) reached a plea deal with federal prosecutors that gave him 51 months in prison and required him to forfeit nearly $44m in ill-gotten gains. In 2012, the Internal Revenue Service subsequently ordered Kaplan to pay an additional $25m in taxes and penalties on his 2004 online gambling earnings and a further $11m for 2005. Kaplan appealed, arguing (amongst other things) that the six-year statute of limitations had invalidated the IRS’ claims against him.

Kaplan took BetOnSports public on the London Stock Exchange in July 2004. Prior to this, Kaplan engaged in several transactions and stock transfers that netted Kaplan and his family members some $98m. This money was placed in two trusts, for which Kaplan was the sole grantor and thus responsible for the taxable income of the trusts. Needless to say, Kaplan paid the IRS bupkis.