In the fall of 1993, Donald Trump was clawing out of the rubble of a cratering business career. Three of his Atlantic City casinos had gone bankrupt. He’d nearly defaulted on $3.4 billion in debt, and, humiliatingly, his creditors had put him on a living allowance: $450,000 a month. Bankers forced him to sell his 282-foot yacht, the Trump Princess, as well as the Trump Shuttle airline and stake in the Plaza hotel, which Trump had once called “the ultimate trophy in the world.” His relationship with Marla Maples had begun in Trumpian glory, with the words “Best Sex I’ve Ever Had” on the front page of the New York Post, but Maples had just given birth to their daughter, Tiffany, and was eager to get married. “I’m going to have to make a decision about Marla...what should I do?” Trump asked his mother around this time. He was 47 years old. Many people in the city believed he was finished.

A source recently passed me a revealing document from this era: Trump’s prenuptial agreement with Maples. Its draconian terms suggest a penuriousness at odds with his public image as a free-spending billionaire in his gilded triplex penthouse. And its confidential financial statements included in the agreement is a sketch of Trump’s immense privilege and the wealth he squandered, telling in both what it illuminates and what is obfuscates.

With Trump fighting House Democrats over the release of his tax returns, what we know about his opaque financial life has largely come from a paper trail unearthed by investigative reporters. Journalists at The New York Times have blazed much of this difficult terrain with bombshells such as the revelation that his father, Fred, bequeathed Trump more than $400 million in today’s dollars, and that IRS tax receipts indicate Trump lost more than more than $1 billion between 1985 and 1994. Dogged reporting by the Times and others revealed Trump’s core argument for being president—he’s a self-made billionaire who alone can solve the world’s most intractable problems—to be as credible as a degree from Trump University. But the deal he made with his second wife was, as a business proposition, a raging success, even though as a personal matter, it was as ugly as could be.

Even Donald Trump realized that, when it comes to romance, a prenup is a buzzkill. “A prenuptial is a horrible document,” he once told a reporter, “because it says, ‘When we get divorced, this is the way we’ll split things up.’ And when you’re a believer in positive thinking, it isn’t good. But it’s a modern-day necessity.”

Raoul Felder, the legendary divorce lawyer whose clients have included Trump’s own lawyer Rudy Giuliani, agreed. “A prenup sucks romance out of the relationship,” he told me. “It’s a prior agreement as to the disposition of money, assets, payments. You basically plan the divorce before you get married.”

Prenup negotiations require both parties to disclose to the other how much money they have. In the document, Trump stated he was worth $1.17 billion; Maples had $100,000 in the bank. But while Trump presented himself as a Master of the Universe, back and bigger than ever, he was, in all likelihood, not an actual billionaire when he signed the agreement. (He didn’t appear on the Forbes list between 1990 and 1995.) And Trump had financial incentive to inflate his wealth: if he understated his fortune, Maples could later claim in a divorce that Trump hid money from her at the time, which could void the prenup’s terms. “When you’re doing a prenup, the worry is you understate your assets. If you overstate it, then you’re protected,” a high-profile Manhattan divorce lawyer told me.