You gotta admire his chutzpah.

“Chutzpah” is a technical tax term that means, “Nice try … but no way we’re going to allow this deduction!”

Attorney William G. Halby, who practiced law for 20 years and specialized in taxation, went all the way to Tax Court. When the members stopped snickering, the Court said no.

Halby’s attempted medical deductions for visits to New York prostitutes and the costs of videos and other pornographic materials were not allowable under the Tax Code.

Brain sturgeon (yes, it’s not a typo – I mean “fish head”) Halby kept journals of the visits, including the date, the name of the “service provider” and the amounts paid over two years. But, the Court complained, the visits were not part of a course of prescribed therapy and he failed to discuss the visits with his doctors afterward to determine the impact on his health.

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Halby may be a tax lawyer. But he should have checked this out with the Tax Corner before taking off his clothes.

Medical expenses are payments you make for the diagnosis, cure, relief, treatment or prevention of disease. They don’t have to be given by a licensed or certified practitioner but must qualify as medical care.

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Halby should have first gone to a doctor, complaining of a medical problem or condition. Perhaps, no blood in his brain because it had all gone to his extremities, or a stiffness that wouldn’t go away? Had the physician then prescribed a course of treatment that included visits to a licensed sex worker in Nevada, the Tax Court would have had a harder time denying his deduction.

Even his travel from New York to Nevada would have been allowable because the primary purpose was for “medical services.”

As my wife Barbie says, “Another example not of planning to fail, but failing to plan.”

So, I’ll just take another toke of my medical marijuana (still not deductible by the Feds even if legally prescribed) and plan my future medical deductions. But, Barbie put me on notice. She’s not taking this lying down. If I actually implement my “plan,” I’d better be prepared to file my tax return as married, filing very separately.

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