Charting an Empire: A Timeline of Trump’s Finances

Illustrations by Justin Metz

The President’s Taxes

Tax records provide a detailed history of President Trump’s business career, revealing huge losses, looming financial threats and a large, contested refund from the I.R.S.

President Trump’s tax returns portray a businessman who takes in hundreds of millions of dollars in some years yet racks up chronic losses.

Playing a tycoon executive on “The Apprentice” earned Mr. Trump nearly $200 million.

Total net income, 2000-2018: $197.3 million

Endorsement and licensing deals that followed the show’s debut brought the Trump name to products and hotels around the world and made him hundreds of millions of dollars more.

Total net income, 2000-2018: $230 million

Investments in companies run by others have been immensely profitable for the president — although he plays no official role in the operations of those businesses.

Total net income, 2000-2018: $178.7 million

Some of Mr. Trump’s own companies generate tens of millions of dollars in profit every year.

Ultimately, however, his own businesses are much bigger losers than winners.

Total net income, 2000-2018: -$174.5 million

The tax returns for Mr. Trump and hundreds of his businesses reveal the hollowness, but also the wizardry, of the self-made-billionaire image honed through “The Apprentice.”

They demonstrate that he was far more successful playing a business mogul than being one in real life.

Total net income, 2000-2018:

Licensing and endorsement deals $230 million
“The Apprentice” $197.3 million
Investments $178.7 million
Companies run by Mr. Trump -$174.5 million

Making a Fortune

Mr. Trump was adrift when he got a big break on “The Apprentice.” He used his reality-TV persona to ink a string of worldwide licensing and endorsement deals.

The tax returns that Mr. Trump has fought to keep secret cast a harsh light on his finances, revealing a businessman who regularly reports losing so much money that he has gone for years paying little or no income taxes and today finds himself in a tightening financial vise.

He has churned through hundreds of millions of dollars in a series of career reinventions, aided by tax-avoidance maneuvers, all laid bare for the first time in tax-return data obtained by The New York Times that extends over more than two decades. The returns comprise information that Mr. Trump has disclosed to the I.R.S., not the findings of an independent financial examination. Even so, the records paint the most complete portrait yet of how Mr. Trump leveraged failure and fame on his improbable path to the White House.

At the start of the new millennium, Mr. Trump was in financial trouble.

The chance to play a reality-TV business mogul on “The Apprentice” changed his fortunes dramatically.

An unusual arrangement with the show’s producers entitled him to half its profits, and as its ratings soared the money rolled in.

In all, “The Apprentice” earned Mr. Trump nearly $200 million.

The show’s success spawned endorsement and licensing deals around the world, generating more than $230 million from 2000 through 2018.

For Mr. Trump, no endorsement was too small, and he rented out his name to everything from Oreo cookies and Domino’s Pizza to mattresses and neckties.

Licensing deals were made with developers of hotels and towers from Azerbaijan and Turkey to Hawaii and Manhattan.

Mr. Trump’s taxes also reveal that his licensing deal in Istanbul has been significantly more lucrative than previously known, with declared earnings of at least $13 million.

Along with “The Apprentice,” the endorsements and licensing deals added up to more than $427 million in reported profit for Mr. Trump in this time period.

The I.R.S. Comes Knocking

Fame brought a windfall to Mr. Trump, but it also left him with something unfamiliar: a large tax bill.

With so much money pouring in from his newfound celebrity and the branding associated with it, Mr. Trump suddenly found himself having to pay income taxes for the first time in years.

Mr. Trump had long managed to sidestep taxes in part because of nearly $1 billion in business losses he incurred in the 1990s and could carry forward to cancel out income in future years. But that option was largely used up by the time his “Apprentice” and licensing profits kicked in, and over a three-year period starting in 2005, he paid over $70 million to the Internal Revenue Service.

They were some of the biggest tax bills of his life and were far more than anything he would owe over the next decade, which would see him pay no taxes at all for five years and only $750 during his first year as president. After a brief period of indebtedness to the I.R.S., he was able to return to tax avoidance by claiming losses on the businesses he owned and operated.

Beyond licensing and endorsements, real estate — in which Mr. Trump had first made a name for himself — remained essential to his bottom line.

Mr. Trump’s retail and commercial spaces at Trump Tower in Midtown Manhattan reported a total of $336.3 million in profit from 2000 to 2018.

And Trump World Tower on the East Side of Manhattan earned Mr. Trump more than $167 million in profit over the same period.

Among his most profitable investments is a 30 percent stake in two office buildings, owned and operated by Vornado Realty Trust. Mr. Trump’s share of the profits totaled $176.5 million through the end of 2018.

But many of his highest-profile properties are money losers, none more so than the sprawling collection of golf courses he bought with profits from “The Apprentice” and licensing deals.

The golf properties have cost Mr. Trump dearly, with declared losses of more than $315.6 million since 2000.

Trump National Doral, a major Florida golf resort, has reported losses of more than $162.3 million.

Turning Losses Into Gold

As his businesses bled money yet again, Mr. Trump used a bold financial move to turn the tables on the I.R.S. and claim a $72.9 million refund.

With the addition of money-losing golf resorts in the United States and Europe, as well as a hotel in the Old Post Office in Washington, Mr. Trump has once again been able to claim annual losses that wash away much of his taxable income. The losses are very real — and some are very large.

Mr. Trump declared more than $1 billion in losses for 2008 and 2009 that appeared to be largely related to the latest, and final, failure of his Atlantic City casino investments. In a particularly audacious accounting move, he used the losses to claim a $72.9 million refund of federal taxes from the previous four years — virtually everything he had paid to the U.S. Treasury during the peak of his “Apprentice” success.

It had echoes of that earlier titanic loss on his returns from the 1990s that resulted in years of tax avoidance. This time, however, the I.R.S. decided to take a hard look at Mr. Trump’s gambit and started an audit, one that has yet to be completed almost 10 years later.

By the time Mr. Trump announced his candidacy in 2015, his revenue streams from “The Apprentice” and licensing were drying up, and he was in need of financial reinvigoration.

If he hoped his unlikely presidential bid might, at least, revitalize his brand, his derogatory remarks about immigrants quickly cost him.

NBC cut ties with the Miss Universe pageant, which it co-owned with Mr. Trump.

NBC also dropped “The Apprentice.” His proceeds from fame continued to tumble, falling below $10 million in 2017 and to $2.9 million in 2018.

At the same time, Mr. Trump’s presidency has, in some respects, helped his business.

At the Mar-a-Lago club in Palm Beach, Fla., a flood of new members starting in 2015 allowed him to pocket millions more dollars a year from the business.

Mr. Trump’s profits reported from the Florida club have risen dramatically compared with the previous decade.

In the end, however, the financial picture for Mr. Trump is fraught.

Danger Signs Ahead

The vise is tightening: Mr. Trump has sold off many of his stocks, the I.R.S. has him under audit and huge bank loans will soon come due.

The president’s tax returns suggest that as he approaches one of the most consequential elections in American history — down in most polls, under I.R.S. audit and heavily in debt — his businesses may not be well equipped to navigate what lies ahead.

As many of his companies continue to lose money, Mr. Trump has more than $300 million in loans, for which he is personally responsible, coming due within the next four years. He liquidated hundreds of millions of dollars in stocks in recent years and may have less than $1 million left in his portfolio, according to his public financial disclosures. The pandemic has crippled the hospitality and recreation industry that so much of his portfolio of properties is dependent on.

And hanging over his head is the audit. Should the I.R.S. reverse the huge refund he received 10 years ago, Mr. Trump could be on the hook for more than $100 million.

Methodology

Figures here reflect net income, or profit, which is calculated by subtracting certain expenses from revenue. These expenses include salaries, rent, the cost of goods sold, taxes and depreciation. The numbers draw on thousands of business tax returns for 2000 through 2018, along with additional tax information.