Just what is an allowable business expense these days? In a story we’ve been following for a bit, a judge has ruled a lawyer cannot claim a medical deduction for hookers and porn expenses.

It’s a travesty, I tell ya! 

William G. Halby is my favorite lawyer. Admittedly, that might not mean much, but I really do like this guy. You see he has been fighting the IRS in court over a few deductions he claimed. The deductions were sizeable and claimed for the money he spent on hookers, penis enhancement pills and porn. He claimed he needed them to help with the stress of his job and such. 

So, why is Mr. Halby my favorite lawyer in the world? Well, claiming such deductions might do it alone. Imagine the chutzpah you would have to have to do it. Still, I needed something more. Well, then there is the simple fact he actually went ahead and sued the IRS over the issue. Now that is a double helping of chutzpah. Still, something is lacking. What is the final characteristic that could make the difference that would push him to the top of my favorite lawyer list?

I know. 

How about the fact Mr. Halby is…79 years old!

Yes, our favorite lawyer was plying the world of sexual exotica in his 70s. Even better, he did a ton of research. How much? Well, the deductions he was trying to claim totaled just under $300,000 from 2002 through 2004. That boils down to $100,000 a year on getting frisky. That is hardly unreasonable! I alone spent…well, never mind. 

I find this case to be incredibly humorous. You probably do as well. Unfortunately, the New York and federal courts have not. All the deductions have been disallowed and Halby has been hit with penalties and interest. He was even hit with a $4,000 accuracy penalty by the feds. Sheesh, some people have no sense of humor!

Are there any lessons we can take from this situation related to taxes? Not really. About the best I can offer is you shouldn’t try to deduct your hooker expenses, no matter how nice she is!