19 Nice-Try Tax Breaks Rejected by the IRS

Everyone wants to lower their tax bill – but sometimes people try a little too hard.

picture of a woman worrying about taxes
(Image credit: Getty Images)

Over the years, taxpayers have concocted a lot of zany arguments to justify their federal tax breaks. We've come up with 19 of the most creative ones that the courts decided did not quite work. You'll see why these taxpayers' arguments didn't fly in court.

Joy Taylor
Editor, The Kiplinger Tax Letter

Joy is an experienced CPA and tax attorney with an L.L.M. in Taxation from New York University School of Law. After many years working for big law and accounting firms, Joy saw the light and now puts her education, legal experience and in-depth knowledge of federal tax law to use writing for Kiplinger. She writes and edits The Kiplinger Tax Letter and contributes federal tax and retirement stories to kiplinger.com and Kiplinger’s Retirement Report. Her articles have been picked up by the Washington Post and other media outlets. Joy has also appeared as a tax expert in newspapers, on television and on radio discussing federal tax developments.