Many of Trump’s businesses spent the 1990s on the verge of collapse. Abraham Wallach, who became the Trump Organization’s executive vice president for acquisitions in 1990, compared joining the company to “getting on the Titanic just before the women and children were moved to the lifeboats.” In 1990, the Trump Organization was reportedly $3.4 billion in debt, with Trump himself liable for over $800 million; the next year, as several of Trump’s hotels and casinos reportedly accumulated millions in debt, the New Jersey Casino Control Commission concluded, “Mr. Trump cannot be considered financially stable.” In 1992, Trump defaulted on the debt of his airline, Trump Shuttle, turning it over to U.S. Airways. Even as Trump broke ground on Trump World Tower in 1998, he was “renegotiating $1.8 billion in junk bonds for his Atlantic City resorts, and the tower was built on a mountain of debt owed to German banks.”

In Trump’s own telling, his fortunes turned around in 1995, when Trump Hotels & Casino Resorts, the company through which he owned and operated many of his properties in Atlantic City and elsewhere, held an initial public offering. In truth, Trump’s financial struggles continued. Contrary to Trump’s own lofty predictions—he mused to Vanity Fair’s Edward Klein that the IPO might raise $4 billion—he only managed to raise $140 million; meanwhile, according to his tax returns from that year (which remain the only of Trump’s tax returns available to the public), Trump declared a loss of nearly $916 million. His businesses continued to struggle, with his casinos posting $66 million in losses by the end of 1996 and another $42 million in 1997. The problems lasted well into the 2000s: Trump’s flagship companies declared bankruptcy in both 2004 and 2009, with Trump resigning from his position as head of the board of Trump Entertainment Resorts in 2009.

Compounding Trump’s financial problems was the Wall Street stigma his business failures attracted. The Guardian has reported that, in the 1990s, “Wall Street banks, which had previously extended him credit, turned off the tap;” according to The New York Times, bankers went so far as to coin the phrase “Donald risk” to describe the widespread aversion to lending to Trump. In 2013, one banker told The Atlantic, “If a major institution in New York—whether it was a Chase or a Goldman or a law firm or something—wanted to have a building built … I can give you almost 100 percent assurance that Donald would not be on the list.”

Amid these financial struggles, Trump turned to two notable sources of capital: Deutsche Bank and Bayrock Group. In 1998, Deutsche Bank provided Trump $125 million to renovate an office building at 40 Wall Street. More deals followed, with the bank providing or underwriting $1.3 billion to Trump entities over the next few years. Trump’s relationship with Deutsche Bank has not always been amicable; in November 2008, he had difficulty making payments on a $640 million Deutsch Bank loan – $40 million of which he guaranteed personally – he took out to finance the construction of the Trump tower in Chicago. He sued the bank for $3 billion, alleging it was partially responsible for the global financial crisis and, by extension, Trump’s inability to repay the loan (the case was ultimately settled). Trump’s connection to Deutsche Bank is particularly notable because the institution has been at the center of schemes to help Russians secretly funnel money offshore, for which it paid “about $630 million in penalties … over a $10 billion Russian money-laundering scheme that involved its Moscow, New York and London branches.”