Forbes, Lamar Odom Seeks Tax Deduction For NBA Fines and Fitness Fees, by William P. Barrett:

Los Angeles Lakers basketball forward Lamar Odom has sued the IRS, which said he couldn’t take tax deductions for $12,000 in sports fines and another $178,000 spent getting himself in shape. …

Odom disputed a bill that the IRS sent him in August. “The taxpayer claimed $12,000 of employee business expenses for fines that were assessed by the NBA,” he declared, writing in the third person. “These fines are commonly assessed on professional athletes and are work related. Therefore the fines incurred are ordinary and necessary employee business expense.” …

Odom … also attacked an IRS decision not to allow taxpayers in effect to subsidize his efforts as a pro athlete to stay fit. “The taxpayer claimed $178,337 of employee business expenses for professional training and conditioning,” he wrote. “The taxpayer’s employment contract requires that the taxpayer be in sufficient physical condition that allows him to perform as a professional basketball player throughout the basketball season.” Tax law and court cases have tended to frown on writing off such items. In the explanation attached to its bill, the IRS wrote Odom, “We have disallowed some of the expenses you claimed as business expenses because it was determined they were personal expenses and not deductible.”