1995 wasn't Donald Trump's first financial hit

By Diana Pearl
Updated October 06, 2016 02:03 PM

Last weekend, The New York Times published Donald Trump’s 1995 tax returns, which show that The Donald suffered a $916 million loss throughout the year.

But it wasn’t his first financial setback. Just five years earlier, Trump covered the June 9, 1990, issue of PEOPLE with a stack of cash — alongside the words “Poor Donald!”

The story came three years after he talked a potential White House run on the cover of PEOPLE in 1987.

Back in 1990, Trump was in the midst of promoting his second book, the follow-up to The Art of the Deal, but things weren’t going so well off the page. Professionally, he was missing payments to cover his debts on his properties, and the Atlantic City casino market was stalling — just months after he opened his Trump Taj Mahal Casino in the city. PEOPLE reported that last-minute, $65 million loan from the banks staved off bankruptcy and default. In return, he was required to control his spending to $450,000 a month. His debt was said to include $500 million or more in personal loans, and some analysts claimed his net worth was less than zero.

His personal life was on an edge, too. Trump’s marriage to first wife Ivana was crumbling. They would divorce two years later, in 1992. Rumors were already beginning to swirl of his affair with Marla Maples, later his second wife. Trump, however, denied that the new relationship was a sign of a “midlife crisis.”

“I don’t believe in mid-life crisis,” Trump said. “I’m not sure there is such a thing, and I’m not sure I’m in mid-life.”

Rather than aging, what some thought was the biggest concern to Trump was his image — and impressing the elites of New York.

“He’s very insecure,” a close personal and professional acquaintance told the magazine at the time. “He’d tell about how when he first moved to New York he was shunned by a lot of people—hardly any invitations to the Hamptons for the weekend and all that. Although he claims he doesn’t care, you know deep down it bothers him.”

Another person who knew him well also spoke out about his vulnerabilities.

“There is in Donald a genuine need to self-destruct. In order to feel real and whole, he had to exceed himself constantly, make more money, build bigger buildings. Underneath there’s despair: Nothing I do is enough, and it never will be. And you can’t outdo yourself forever, so you have to f—- it up and start over.”