Donald Trump has a unique bond with Wall Street. His grandfather, a German immigrant, ran a barber shop on the ground floor of a newly constructed building at 60 Wall Street. Later, the site became home first to JPMorgan and then to Deutsche Bank—for many years Trump’s house bank. When Trump wanted to buy an art deco skyscraper a block away at 40 Wall Street, Deutsche was there to lend him money for renovations. 

But his relationship with Wall Street institutions is checkered. As a property developer, Trump was heavily reliant on their financing to fuel his business. In 1988, he hired Merrill Lynch to help raise $675 million to fund a new casino in Atlantic City. Billed as the eighth wonder of the world, the Trump Taj Mahal Casino and Resort was the world’s largest casino when it opened two years later. Within months, it was in default. Alongside two other Trump properties in the city, revenues sagged as recession hit and bond coupons at 14% proved too much to bear. Trump agreed with creditors to reschedule the debt to buy himself time, while also drawing down loans from Citibank, Bankers Trust (now part of Deutsche Bank), Manufacturers Hanover (now part of JPMorgan), NatWest and others.

Trump’s Atlantic City casinos would return to the bankruptcy courts four times in total. A stock market listing in 1995 introduced fresh capital but it was insufficient to deleverage the business adequately. Every few years, lenders took a haircut. Over a ten year period, the New York Times estimates that stock and bondholders lost more than $1.5 billion. 

During that time, bankers started to avoid Trump. Even his friend Ace Greenberg, chairman of Bear Stearns, refused to lend him money. Trump himself reveals why in his book, Think Big and Kick Ass in Business and Life, where he reflects on how he handled lenders during the 1990s downturn. “I turned it back on the banks and let them accept some of the blame,” he writes. “I figured it was the banks’ problem, not mine. What the hell did I care? I actually told one bank, ‘I told you you shouldn’t have loaned me that money. I told you that goddamn deal was no good.’”

One lender that didn’t get the memo was Deutsche Bank. Keen to bolster its credentials in New York, it agreed to lend Trump $125 million in 1998 to finance renovations at 40 Wall Street. Another loan soon followed to fund construction of a tower across the street from the United Nations. Over the next two decades, Deutsche Bank would lend Trump more than $2 billion. 

Its close relationship with Trump made the bank central to the New York Attorney General’s case against him over financial statement fraud. Its files on Trump properties were error-strewn, exaggerating their height and floor area and also his net worth. Based on the square footage available in its records, Deutsche once valued 40 Wall Street at $542 million. The bank is no longer involved in financing it, but the building is likely worth a lot less today. Of the 75 tenants listed on its rent roll ten years ago, more than 40 have left and vacancy is high. In the first six months of the year, the building is on track to generate less than $8 million in net income, insufficient to cover the $9.8 million owed in debt service. 

Deutsche Bank never lost much money on Trump but it was a close call. In 2005, it lent him $640 million to build a 92-story skyscraper in Chicago. By the time the loan was due, the global financial crisis was in full swing and Trump couldn’t pay. Instead, he filed a lawsuit claiming the crisis represented a force majeure and accused Deutsche of predatory lending practices. “Deutsche Bank is one of the banks primarily responsible for the economic dysfunction we are currently facing,” he asserted, seeking $3 billion in damages. 

The case was eventually settled but by then, Trump had found other sources of financing. His main bank today is a small, California-based firm called Axos Financial. Together with its largest individual shareholder, the bank has extended more than $500 million in financing to Trump. His election win having bolstered his creditworthiness, Axos stock leaped, rising 22% as soon as the result became clear. 

Axos wasn’t the only financial institution to benefit. Despite Wall Street’s troubled track record with Trump, many winners emerged in the sector on election night. To explore some of them, starting with Fannie Mae and Freddie Mac, read on...