As cartoon plutocrat and sentient overripe pear Donald Trump officially entered the Republican presidential race Tuesday, he pointedly brandished a financial disclosure statement that asserts his net worth to be in the neighborhood of 9 billion dollars. How much is Trump really worth? If history is any guide, the safe answer is: much less than he says he does.

Here’s a timeline of how much money—visualized with the help of graphs—Donald Trump has claimed to have through the years, and how accurate those claims were according to the best sources available at the time.

Trump had accounting firm Arthur Andersen—which would later be disgraced in the Enron scandal—audit his finances in 1988, revealing he had more than $700 million in cash and liquid assets.

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But according to Spy, which gleefully deflated many of Trump’s lofty public claims in the late ‘80s and early ‘90s, this was a neat deception. The Andersen audit took place a week after Merrill Lynch had given Trump $651 million to build his famous Trump Taj Mahal casino in Atlantic City, and it failed to note that all that cash was already earmarked for the project.

Most of Trump’s remaining assets were in stock, but the accountants also didn’t point out that those shares were bought with borrowed money—he still owed $69 million.

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By Spy’s math, Trump was actually $20 million in the hole at the time.

Trump’s Greatest, Most Luxurious Estimate: $700,125,000
Estimate From the Haters and Losers: $-20 million

From the same Spy piece by John Connolly (coverline: “Was Donald Trump Ever Really Rich?”): Trump filed a sworn statement with New Jersey’s Casino Control Commission in March 1990, listing his assets at $1.5 billion.

Just months later, his own bankers valued his short-term assets, everything he could sell within 90 days, at “between $282 million and negative $295 million.”

Also that March, divorce lawyers for The Donald’s then-wife Ivana Trump argued she was entitled to half of his assets—which they valued at $5 billion—in spite of their prenuptual agreement.

“But the erstwhile billionaire apparently never had that much to begin with and certainly does not have it now,” The New York Times reported in 1991, “Mr. Trump’s financial problems brought him near bankruptcy last year and forced him to ask his banks to rescue him by lending him more money to pay off bills.”

Trump himself wouldn’t have gone as high as $5 billion that year, especially with the risk of losing half. This might be the only time he’s ever admitted he had less money than people thought.

In May 1990, Forbes published its famous cover story, “How Much Is Donald Trump Really Worth Now?” asserting that “we come up with properties that we think have a market value of slightly less than $3.7 billion and are encumbered by nearly $3.2 billion in debt. If our estimates are substantially correct—and we think they are generous—Donald Trump’s current net worth is about $500 million.”

A few billion dollars and several strategic bankruptcies later, everyone still suspects Trump of exaggerating the hell out of his actual assets.

Trump’s Greatest, Most Luxurious Estimate: $1.5 billion (sorry, Ivana)
Estimate From the Haters and Losers: $500 million

“When I was in trouble in the early 90’s, I went around and — you know, a lot of people couldn’t believe I did this because they think I have an ego — I went around and openly told people I was worth minus $900 million,” Trump told the New York Times in 2005. “And then I was able to make a deal with the banks.”

Trump’s Greatest, Most Luxurious Estimate: $-900 million
Estimate From the Haters and Losers Who Believe That Donald Trump Has An Ego: n/a

Trump returned to the Forbes list after a six-year absence, but according to the magazine, he was not precisely pleased:

“Trump, polite but unhappy, phoning from his plane: ‘You’re putting me on at $450 million? I’ve got that much in stock market assets alone. There’s 100 percent of Trump Tower, 100 percent of the new Nike store — they’re paying $10 million a year in rent!’ Add it all up, said Trump, and his net worth is ‘in the $2 billion range, probably over $2 billion.”’

Trump’s Greatest, Most Luxurious Estimate: Probably over $2 billion
Estimate From the Haters and Losers: $450 million

“He puts his net worth at $5 billion,” the Wall Street Journal reported, but Abraham Wallach, a Trump Organization executive VP, said, “Donald exaggerates sometimes. He’s talking of futures.”

The WSJ piece went on to suggest that Trump was overvaluing his casinos and many of his real estate assets, basically “counting chickens before they hatch.”

At the time, he valued his largest asset, the still-under-construction Trump Place—which would eventually become Riverside South, the largest residential development in Manhattan—at $2 to $3 billion. In 2005, the development’s Southeast Asian financiers, Hudson Waterfront Associates, sold it for $1.76 billion. Trump sued, contending they could have gotten at least $3 billion, but his claims were dismissed.

As of 2006, Forbes valued Trump’s stake in the West Side development at $170 million, far shy of the billions he expected it to bring in back in 2000.

Trump’s Greatest, Most Luxurious Estimate: $5 billion
Estimate From the Haters and Losers: Less.

Journalist Tim O’Brien, who reignited the speculation about Trump’s true net worth with his 2005 book Trump Nation: The Art of Being the Donald, recorded this hilarious anecdote about a meeting with Trump in the New York Times that year:

“I would say six [billion]. Five to six. Five to six,” he said.

Hmm. The previous August he told me that his net worth was $4 billion to $5 billion. Then, later that same day that August, he said his casino holdings represented 2 percent of his wealth, which at the time gave him a net worth of about $1.7 billion. In the same day, Donald’s own estimates of his wealth differed by as much as $3.3 billion. How could that happen? Was Donald living in his own private zone of wildly escalating daily inflation, a Trump Bolivia? And his $1.7 billion figure in August was well below the $2.6 billion that Forbes would credit him when it published its rich list just a couple of months later.

Now Donald was saying he was worth $5 billion to $6 billion.

“Five to six. Five to six.”

And on the nightstand in my bedroom at Donald’s Palm Beach club, Mar-a-Lago, was a glossy brochure that said he was worth $9.5 billion.

LOL.

That same year, Deutsche Bank did an independent evaluation of Trump’s net worth before giving him a $640 million loan to build condos in Chicago, the Wall Street Journal reports. They determined he was worth $788 million.

Trump’s Greatest, Most Luxurious Estimate: $4-5 billion and $5-6 billion and $9.5 billion
Estimate From the Haters and Losers: $788 million.

Trump sued O’Brien for libel a year after his book was published, claiming his net worth was actually $6 billion, not the $150 to $250 million O’Brien reported based on sources who’d seen Trump’s finances. In the process of making his case, Trump cited that year’s Forbes list, which put him at $2.7 billion—lower than he liked to claim, but better than being a mere millionaire.

Is the Forbes figure accurate? O’Brien argues that Trump has always been the owner of “verbal billions,” whose bragging tends to blur the line between properties he’s built and properties he actually owns. Although Forbes never credits him with the unbelievable numbers he claims, the magazine’s figures are nonetheless skewed because it’s forced to rely on the Trump Organization for information.

As O’Brien put it, “Donald and The Forbes 400 were mutually reinforcing.”

Forbes admitted this week that “every year, Trump shares a lot of information with us that helps us get to the figures we publish. But he also consistently pushes for a higher net worth—especially when it comes to the value of his personal brand.”

(Forbes isn’t the only magazine Trump pushes to over-report his wealth. In 2000, Fortune reported that “Trump called so many times to haggle over his net worth that an intern was assigned to field his calls.”)

As for O’Brien’s figures, he wrote that he’d be willing to add as much as $170 million to his estimate based on the value of Trump’s casinos. Since then, Trump’s casino business has gone through bankruptcy twice. Of his former Atlantic City holdings, only the Taj Mahal remains open—The Donald is completely uninvolved in its management. (And even that would be at risk of closing if new owner Carl Icahn hadn’t been ordered to keep it operating as a condition of Chapter 11.)

Trump’s Greatest, Most Luxurious Estimate: $6 billion
Estimate From the Haters and Losers: $150-250 million

Trump’s suit against O’Brien was dismissed in 2009, with the question of Trump’s actual fortune still unsettled, because Trump couldn’t prove O’Brien had been malicious by relying on his anonymous sources. At the conclusion of the suit, Trump still claimed to be worth $6 billion, the same figure as when the suit began 3 years earlier. (Forbes listed him at $2.6 billion.)

During a deposition for the case, Trump and an attorney had the following absolutely amazing exchange:

Q: Let me just ask you first about the first sentence there: Trump relentlessly bloviating about his developments — this is going to be the biggest, best, most amazing — leads people to assume he exaggerates his net worth. Do you see that?

A: Yes.

Q: Do you know what bloviating means?

A: Well, I’m not sure that there’s an exact definition, but I would imagine that’s what it means.

Q: Exaggeration?

A: Could be, yeah.

Q: Lying?

A: No.

Whether Trump’s estimations of his own net worth are lies, exaggerations, or fantasies he clings to, there’s no denying that he uses some unorthodox accounting methods in in determining them. In the same deposition, he claimed he’d done “mental projections” to arrive at the future value of one of his developments.

Trump’s Greatest, Most Luxurious Estimate: $6 billion, still
Estimate From the Haters and Losers: $2.6 billion

Trump lost an appeal of his libel suit against O’Brien, and his lawyer told reporters his net worth had been “proven conclusively” to exceed $7 billion.

(This is the same case where Trump testified that he just tacked on 4, maybe 5 billion dollars to his net worth to account for the value of his brand.)

Trump’s Greatest, Most Luxurious Estimate: $7 billion, proven conclusively
Estimate From the Haters and Losers: $2.9 billion, per Forbes

While talking to the Washington Post about the possibility of a 2016 presidential bid, Trump estimated his net worth at “probably over $10 billion.” This is the largest, most ridiculous figure Trump has ever publicly claimed.

At the time, Forbes listed him at $3.2 billion, but the Post reports Trump waved away the discrepancy by saying his business ventures had been very successful that year. (Almost $7 billion worth of successful? Highly unlikely.)

Trump’s Greatest, Most Luxurious Estimate: Probably over $10 billion
Estimate From the Haters and Losers: $3.2 billion

The only good likely to come from another Donald Trump run for president (besides, of course, the Content) is the chance to study his public filings for information that could help us determine how many of his “verbal billions” are real, actual billions. In the sparse document released (and waved around) Tuesday, Trump claimed a net worth of $8.7 billion as of June 2014.

Two things in particular jump out in Trump’s “Summary of Net Worth” document: First, his single most valuable asset is apparently the Trump brand and the licensing deals it brings in. He values Just Being Donald Trump at more than $3.3 billion. According to Forbes, his brand is only worth $125 million, plus “another $128 million in management fees for Trump-branded hotels.”

Second, in his list of liabilities, he counts loans and mortgages only on real estate owned 100 percent by him—and, as we’ve seen, much of what says “Trump” on it isn’t wholly owned by The Donald himself.

“Typically Mr. Trump, having once lost his shirt, risks little money but earns a profit—paid only after lenders and partners get their money back—by acting as developer and promoter,” the Wall Street Journal noted in 2000.

And what if those developments never turn profitable? Trump doesn’t like to talk about that. In a 2007 deposition for the O’Brien lawsuit, he asked lawyers, “Would you like me to say, oh, gee, the building is not doing well, blah, blah, blah, come by, the building — nobody talks that way. Who would ever talk that way?”

Forbes also argues that Trump is wildly overvaluing his clubs and his golf course chain—to the tune of about a billion dollars—and rightly declines to credit him $300 million for properties that haven’t been built yet. In terms of assets that can be confidently confirmed, Trump has $300 million in cash and securities, and owns about $3 billion dollars worth of real estate. By their math, the math of the haters and losers of the world, Trump is worth 4 billion dollars, or less than half of what he claims.

[Images by Jim Cooke]