8 Outrageous Tax Write-Offs (Slideshow)


Did you participate in any illegal activities in 2011? Did you spruce up your house or take any tropical vacations? Well, you’re in luck — check out these completely ridiculous deductions you may be able to use on your taxes!

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1. Caribbean Vacation.

Itching to take a trip to the beach, but want to be economical about it? Just plan a business meeting to one of the many Caribbean islands, Central American countries (and even Canada) that the IRS allows you to write off. Unlike destinations across the pond, you don’t need to justify your reason for planning a meeting or convention outside of the U.S.

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2. Home Office — For a Drug Dealer!

In 1981, a Minnesota drug deal was found to owe the IRS $17,000 in back taxes for income earned from selling illegal drugs. He successfully appealed his audit on the grounds of his home office deduction. He still went to prison, though!

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3. Private Plane.

One couple was successfully able to justify their private airplane travel as a necessary business expense — they couldn’t possibly drive or rely on a once daily commercial flight to check on their tenants in a building 5-7 hours drive away!

4. Swimming Pool.

Don’t get too excited about this one — you need to prove that you have a legitimate medical need to write off the expenses of building a home swimming pool. A man with emphysema successfully wrote off his pool after proving the exercise improved his condition.

Related: What Medical Expenses Can Be Written Off on Taxes?

5. Money Owed to You by Family Members.

Did you lend money to a family member and really don’t expect it back? Well, the IRS will let you write off up to $3,000 of that bad loan, as long as you prove that you had a payment plan in writing and why you think you won’t be seeing it any time soon.

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6. Landscaping.

Got a one person shop at your home where you regularly meet with clients? You can write off part of the costs of landscaping, driveway repair and lawn care!

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7. White Collar Crime.

Businesses can write off the expenses of punitive damages awarded to victims of corporate crime. BP, for instance, can write off the money it gave to the family members of victims who died in the Gulf oil spill.

8. Totaled Car From a Drunk Driving Accident.

After drinking alcohol at a friend’s party, a Texas man totaled his $40,000 truck and was arrested for driving under the influence. His insurance company rejected his loss claim, so the man instead filed it as a casualty loss deduction on his taxes. The IRS rejected this claim, and the man went to court; the judge eventually decided in favor of the drunk driver, not the IRS!

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Jeanne Schlatter
Jeanne Schlatter1 years ago

Thank you for sharing.

Jeanne Rogers
Jeanne R1 years ago

Thank you for sharing.

Kathy Perez
Kathy Johnson5 years ago

wow... hmm.. landscaping, vacation? hell yes! and ouch.. my uhmmm... back. yes. i need a pool. lol

Kimberly McMahen
Kimberly McMahen5 years ago


Lika S.
Lika P5 years ago

Only a rich, corrupt, corporate person would do these things.

Heidi Aubrey
Heidi Aubrey5 years ago

No justification or proof for a tropical "business meeting". Wow.

Mary Donnelly
Mary Donnelly5 years ago

Thanks for this one; let's hope it makes legislators think.

Anne F.
Anne F5 years ago

Don't think that giving tax advantages to people working from their homes is a problem. Would like to see a minimum tax imposed on corporations and individuals - would like to see GE and Boeing pay their fair share.

Teresa Cowley
Teresa Cowley5 years ago

You're correct in saying that these write-offs ARE outrageous!

Nadine Hudak
Nadine H5 years ago