You can still deduct the cost of sex therapy as a medical expense. This includes the cost of hotel room and transportation if prescribed by the therapist. Cheaper Than A Divorce . You can deduct legal fees for committing your mentally-ill spouse to an insane asylum as a medical expense. Cost of Running an Illegal Business .
Crime pays . .
Money you make from an illegal business are taxable just like any other income. But the IRS generously lets you deduct the legitimate costs of running the business. That means bookies can deduct their phone costs, and so forth. Unfortunately, there s no deduction for illegal expenses. That means if Tony Soprano ever gets up the nerve to whack out his mom, he'll have to do it on his own dime.