• Home
  • News
  • Fortune 500
  • Tech
  • Finance
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
FinanceTaxes

Donald Trump Gets Tax Breaks. How You Can Too

By
Ian Salisbury
Ian Salisbury
and
Money
Money
Down Arrow Button Icon
By
Ian Salisbury
Ian Salisbury
and
Money
Money
Down Arrow Button Icon
October 4, 2016, 12:04 PM ET
Presidential Candidates Address AIPAC Policy Conference
Alex Wong—Getty Images

This story originally appeared on money.com.

The latest surprise in this year’s presidential campaign: A bombshell New York Times report that Donald Trump’s 1995 tax return included a $916 million loss that may have allowed him to avoid paying federal income taxes for nearly 20 years.

Whatever you think of the politics of our tax system, taxpayers who aren’t business owners, much less real estate tycoons like Trump, can get a tax break when some aspect of their finances turns sour. The result is nowhere near what business owners get, but at least it’s something.

In fact, while the amounts cited in Trump’s returns are certainly striking, the strategy that experts think he could have used to trim his bill — counting past business losses against future income — isn’t unusual. Indeed, roughly 1.2 million taxpayers, typically small business owners, took similar deductions in 2014, according the Tax Foundation.

And to many, the provision makes intuitive sense. It allows a business that is wildly profitable one calendar year, but loss-making the next, to even out its income in the eyes of the IRS, according to Tax Foundation economist Alan Cole. “A year is basically an arbitrary unit of time,” he says.

True, if you earn a salary, the situation might strike you as unfair. Many endure big swings in income throughout their lives: Students who go into debt to pay for a degree; salespeople who earn a large bonus one year and none the next; laid-off factory workers who must spend down savings until they find a new job.

Read Next: Donald Trump’s Accountant Likely Violated Confidentiality Rules

In general, though, the IRS doesn’t allow them to count lean years against the fat ones. “If we let people smooth their incomes, they would pay a lot less taxes,” says NYU Law Professor Lily Batchelder.

Nevertheless, here are four examples of tax breaks for you, however modest in relation to what Trump enjoys:

Your Investment Portfolio

Chances are you’ve never bought or sold a casino or hotel. But you may very well have traded a stock or a bond. And if so, there is a good chance that at one time or another you’ve sold at a loss. The good news is these losses — indeed losses on most investments, including real estate — can lower your tax bill, reducing dollar for dollar any capital gains you realized from selling winning investments in the same year.

What’s more, if your losses outstrip your gains, you can carry them forward into future years to offset later profits. There is a disadvantage, however. Unlike business owners who report business profits or losses on their personal income tax returns, the law imposes a strict limit on how much stock market or other investment losses can offset ordinary income, like your salary, which is typically taxed at a higher rate. The IRS allows you to count no more than $3,000 in capital losses against your ordinary income in any given year.

Your Interest in a Business

Many of us who aren’t small business owners may still own a slice of a business, perhaps a small share of a buddy’s restaurant or an Internet startup. This business has a reasonable chance of generating operating losses (especially if it’s a restaurant or Internet startup.) Like your capital losses, these too may lower tax bills. But unless you are actively involved in managing the business, you get less favorable treatment than an owner-operator.

In general, losses from that business can be used to offset your income and carried forward for future years, but this only applies to income from that particular business. Unlike people who run their own business, including Trump, you cannot use the losses from the enterprise to offset other income, such as your salary.

Read Next: 10 Times Donald Trump Bad-Mouthed People for Not Paying Taxes

While the distinction between those who manage a businesses and other investors may seem like an odd one, it’s not by accident. The distinction was created by Congress in 1986 to curb money-losing business deals that many argued existed primarily as tax shelters.

Your Rental Property

The rules for rental properties are even stricter than for other types of businesses. This real estate is where some of the biggest abuses occurred in the 1980s, prompting the 1986 tax reform. If you own a rental property, you typically count as a passive investor — meaning you can’t count losses against your ordinary income — even if you manage the property yourself.

A couple of exceptions exist, according to Michael J. Amato, president of Independent Tax & Financial Planners PC, in Holland, Pa. One is if managing real property is your full-time job. The other is if you don’t make much other income. Taxpayers with adjusted gross income (that’s income after deductions and other adjustments) of $100,000 or less, who also actively manage their properties, can claim rental losses of up to $25,000. That $25,000 phases out by the time your adjusted gross income exceeds $150,00o, although wealthier landlords may still be able to use any losses that remain when it finally comes time to sell the property.

Your Home

Trump is hardly the only American to lose money in real estate. Million were hit hard by the financial crisis. About one in 10 homeowners is still underwater, according to real estate data site Trulia.

One consolation: The first $250,000 on your home sale profit ($500,000 for a couple) is free from capital gains taxes. Above that, you’re taxed. Meanwhile, selling the property at a loss confers little in the way of tax benefits.

Not only does the IRS not let you count the loss against your current or future income, it can’t even use it to offset other capital gains, such as on the sale of stocks. “It’s a little counter-inutitive,” says Trulia’s chief economist, Ralph McLaughlin. “You are taxed on the gain, but there is no relief on a loss.”

About the Authors
By Ian Salisbury
See full bioRight Arrow Button Icon
By Money
See full bioRight Arrow Button Icon

Latest in Finance

Travel & LeisureBrainstorm Design
Luxury hotels need to have ‘a point of view’ to attract visitors hungry for experiences, says designer André Fu
By Nicholas GordonDecember 4, 2025
3 hours ago
Personal FinanceCertificates of Deposit (CDs)
Best certificates of deposit (CDs) for December 2025
By Glen Luke FlanaganDecember 4, 2025
8 hours ago
The Fifth Third Bank logo on a blue and purple layered background.
Personal Financechecking accounts
Fifth Third Bank review 2025: Full-service bank with unique perks (but lackluster APYs)
By Joseph HostetlerDecember 4, 2025
8 hours ago
Trump
PoliticsWhite House
‘We fixed inflation, and we fixed almost everything’: Trump travels to Pennsylvania to talk affordability while denying it’s a problem
By Josh Boak and The Associated PressDecember 4, 2025
9 hours ago
Bear
RetailTariffs and trade
Build-A-Bear stock falls 15% as it reveals the real hit from tariffs, at last
By Michelle Chapman and The Associated PressDecember 4, 2025
9 hours ago
Gen Z
EconomyGen Z
America, meet your alienated youth: ‘Gold standard’ Harvard survey reveals Gen Z’s anxiety and distrust, defined by economic insecurity
By Nick LichtenbergDecember 4, 2025
9 hours ago

Most Popular

placeholder alt text
Economy
Two months into the new fiscal year and the U.S. government is already spending more than $10 billion a week servicing national debt
By Eleanor PringleDecember 4, 2025
18 hours ago
placeholder alt text
Success
‘Godfather of AI’ says Bill Gates and Elon Musk are right about the future of work—but he predicts mass unemployment is on its way
By Preston ForeDecember 4, 2025
13 hours ago
placeholder alt text
North America
Jeff Bezos and Lauren Sánchez Bezos commit $102.5 million to organizations combating homelessness across the U.S.: ‘This is just the beginning’
By Sydney LakeDecember 2, 2025
3 days ago
placeholder alt text
Success
Nearly 4 million new manufacturing jobs are coming to America as boomers retire—but it's the one trade job Gen Z doesn't want
By Emma BurleighDecember 4, 2025
14 hours ago
placeholder alt text
Success
Nvidia CEO Jensen Huang admits he works 7 days a week, including holidays, in a constant 'state of anxiety' out of fear of going bankrupt
By Jessica CoacciDecember 4, 2025
13 hours ago
placeholder alt text
Health
Bill Gates decries ‘significant reversal in child deaths’ as nearly 5 million kids will die before they turn 5 this year
By Nick LichtenbergDecember 4, 2025
1 day ago
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.