Tax Lawyer's Blog

I thought I was an aggressive tax preparer, listen to the deductions these wackjoints tried to take:

Arsonist Expenses

I kid you not. A man paid an arsonist $10,000.00 to burn down his furniture store warehouse. The plan was not only to collect the $500,000 insurance money, but also to deduct the $10,000 expenses of hiring the arsonist. The deduction was denied. I guess arsonist expenses may be necessary, but they sure aren’t ordinary.

Fake Ta Ta’s

A strip tease, ahem, “artist”, named Chesty Love bought breast implants to boost her tip income.  Believe it or not, the IRS allowed the deduction on the grounds that it was a stage prop essential to her act.

But I think size 56-FF was overkill, don’t you?  I mean, those aren’t boobs, they’re dirigibles.

Oh the humanity!

Sperm Depletion

This fertile feller properly included the income he received for making regular deposits at his local area sperm bank. So far, so good.  But then he tried to offset that income by taking a deduction for sperm depletion.

It’s not as bad an argument as you might think. I mean, can you think of a more natural resource?

Prostitute Expenses

A business man insisted that his CPA include a deduction on his return for the cost he incurred in hiring a prostitute to entertain his customers.  When the CPA told his client that he’d have to get the call girl’s name, address and social security number so he could issue a 1099 to her, the businessman backed off.  Paying someone for sexual favors is illegal, therefore, the businessman gets no deduction even if he could prove it was an ordinary and necessary entertainment expense.  But what about Charlie Sheen? He said he didn’t pay call girls to sleep with him, he paid them to leave.  Hmmmm.

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