Opens in a new tab

Wacky tax deduction time

February 10, 2010

By now I'm sure you've heard about the recent Tax Court ruling that gender reassignment surgery costs are deductible medical expenses.

You didn't? Then check out TaxProf's item on the ruling. He also includes lots of related links if you want to read even more.

While that was case covered serious medical, social and tax matters, every year we get lots of taxpayers who simply try to get one (or more) obviously questionable deductions past the IRS.

My Bankrate.com colleague Jay MacDonald has just compiled his latest look at some of this year's Wackiest tax deductions.

Texas tax twists: I must say I got a chuckle out of a couple of Texas mentions: Willie Nelson and an Austin accountant who was "steered" wrong.

No, Willie's not in tax trouble again. He was cited as an example of someone who can legitimately claim a lot of business travel miles, unlike one clearly questionable road warrior. That guy claimed he traveled so much that his own accountant, who ran the numbers, said "it would have required him to be driving continually all year."

Then there's an Austin CPA whose city upbringing didn't prepare her for some decidedly country deductions regarding breeding stock.

Yep, as I mentioned yesterday in Stick to the tax man, folks sure to get creative during filing season.

If you want to check on some legitimate write-offs, in addition to the daily tax tips, check out this deductible quiz.

Related posts:

Want to tell your friends about this blog post? Click the Tweet This or Digg This buttons below or use the Share Thisicon to spread the word via e-mail, Facebook and other popular applications. Thanks!

Share:

The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

Latest Posts
confused office worker
8 workplace benefits questions to ask this enrollment season

October 26, 2026

Millions of U.S. workers are now deciding what workplace benefits, some of which also offer…

Read More
TAX-SAVVY WAYS 
TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

Credits/Deductions
Disasters
Family
Filing and Paying Taxes
Politics/Laws
Refunds
State Taxes
Tax Brackets/Inflation
Tax Tips
Comments
Leave your comment