Most of us fill out our forms and pray that a math error won't result in tax debt, an audit, or men in dark suits showing up at our work and carting us off to tax prison. But the truth is that the IRS isn't nearly as draconian as people think.
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How Automation is Driving Efficiency Through the Last Mile of Reporting
The 7 Most Insane Ways People Legally Avoided Paying Taxes
1. The 7 Most Insane Ways People
Legally Avoided Paying Taxes
Most of us fill out our forms and pray that a math
error won't result in tax debt, an audit, or men in
dark suits showing up at our work and carting us off
to tax prison.
But the truth is that the IRS isn't nearly as draconian
as people think. There is a huge range of things
you're allowed to write off from your taxes if you can
make a decent enough argument. And some of them
are truly insane.
2. #7. Crashed Car
Deduction
In 2005, a man and his truck slid off an
embankment. The police found him legally
drunk and fined him with a DUI. The
insurance company denied his insurance
claim of $33,629. He then tried to deduct
the loss of the vehicle from his taxes. Like
the insurance company, the IRS turned
him down. He then brought the case to
U.S. Tax Court to try to force the issue.
He believed he deserved a casualty loss
deduction for his damaged truck whether
or not he was illegally intoxicated when
he damaged it. Incredibly, the judge
agreed. He got to take the deduction.
3. #6. A 70 Cats care
deduction as a
Charity
A cat-loving woman named Jan would go
out of her way to capture random feral
cats on her street and care for them in
her home, at one point housing over 70
cats. For her 2004 tax return, Jan tried to
write off $12,068 for all her cat "rescue"
items like cat food, vet bills, paper towels
and other supplies. The IRS denied this
deduction, asserting that these were
personal expenses. Jan fought the IRS,
insisting that her cat rescue activities
were volunteer work for IRS-qualified
charity, “Fix Our Ferals.” In the end, she
managed to beat the IRS and got
deductions for most of her claims.
4. #5. Illegal Bribes
Deduction by A
Corrupt Businessman
An unethical businessman ran several
companies in the '70s and '80s. In 1984, his
company began doing business with Ford,
and in order to get some fake invoices
that would let him skim money from his
own company undetected, he bribed some
people there to the tune of $180,000. He
was eventually caught and charged with
defrauding the American government. The
IRS was determined to get back the taxes
he avoided with the fake invoice scheme.
If he made money, he owed taxes on it,
even if the money was made illegally. He
filed a petition to the Tax Court, claiming
the under-the-table payments as legal
“operating losses.” The court agreed.
These deductions wound up slashing his
taxable income by a quarter.
5. #4. Gambling Losses
Deduction
In 2001, a habitual gambler bet $131,760
on horse racing and collected $120,463 on
his wagers. So, he wound up in the hole.
Naturally, on his tax return for the year he
listed $10,968 in expenses for travel to
the racetracks, research and
"handicapping information.” When these
expenses were denied, the gambler
challenged the IRS and after a decade the
court ruled with him. The court
established that since gambling was in
essence his profession, these were not
gambling losses, but business expenses.
This was a very important case, as it
deemed on a federal level that being a
professional gambler is an actual job.
6. #3. An Exotic Dancer
Deducts Her Implants
An exotic dancer with the stage name
“Tonda Marie” made less than other
dancers due to her "hereditary deficiency,"
average-sized breasts. So, she decided to
get breast implants to make a better
living and chose an abnormally large size:
56 FF. Naturally, she decided to deduct
the implants as a business expense. When
the IRS said no, the exotic dancer pressed
the point, saying that when she went back
to work, her fees and tips doubled. She
asserted that breasts were so large they
could only be used for business purposes.
In fact, she planned to have them
removed once she retired from dancing. In
the end, a tax court allowed her to deduct
the expense.
7. #2. An NBA Player
Deducts His Fines
A professional basketball player became
an amateur tax lawyer when in 2010 he
received a $87,000-plus interest bill
concerning his 2007 taxes, as well as a
letter saying he was not allowed to deduct
$172,000 in "fitness fees" and $12,000 in
NBA fines from his 2007 tax return. The
player challenged the IRS' ruling, claiming
that the fitness fees were ordinary and
necessary for his job as a professional
athlete and that the fines were an
ordinary and necessary employee business
expense. Eventually he settled with the
IRS, and though not a complete victory, he
paid a fraction of what he originally owed.
8. #1. A Drug Dealer
Deducts His Drugs
Back in 1975, a drug dealer was busted and
charged with drug trafficking. When the IRS
found out about his drug related income,
they came after him for $17,000 in back
taxes on the unreported income. So, the
dealer filed a tax return that listed his
taxable net income and a list of drug-related
business deductions. When the IRS denied
the deductions, the drug dealer fought back
and eventually ended up in Tax Court. He
claimed that he established a business in his
home, which would've qualified him for
a home office deduction, and he named
several purchases - including his drugs - as
necessary business expenses. Impressed with
his honesty, the judge allowed him to deduct
these expenses. Tax law has since been
changed to disallow business deductions that
deal with the trafficking of illegal
substances.
9. To Learn More
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Source: Fulton, Dennis. “The 7 Most Insane Ways People Legally Avoided Paying Taxes.” Cracked. Demand Media Inc., 15 April 2012. Web. 15
January 2016. <http://www.cracked.com/article_19772_the-7-most-insane-ways-people-legally-avoided-paying-taxes.html>