There are many things about lawyering that are good: a certain meticulousness about record keeping, value delivered and value received.
And then there is taking it too far. Take, for instance, the case of William G. Halby, a New York tax lawyer who was admitted to the bar in 1956. When he filed his taxes, he claimed significant deducations, including $108,086 spent on prostitutes and $7,373 on pornographic materials (each over a two year period). He claimed the services as medical expenses.
The tax court did not see the issue his way, finding the expenses were personal in nature and not prescribed by a doctor. http://legalblogwatch.typepad.com/legal_blog_watch/2009/09/tax-court-writes-off-lawyers-deduction-for-prostitutes-1.html
The U.S. Tax Court did note that Halby was meticulous in his record keeping, making entries in a journal for the date, name of service provider and amount. He failed, however, to garner receipts.
The N.Y. Division of Tax Appeals had previously ruled that “permitting the deductions would be counter to public policy.”