PRESDIENT TRUMB

Big German Bank, Key to Trump’s Finances, Faces New Scrutiny

During the presidential campaign, Donald J. Trump pointed to his relationship with Deutsche Bank to counter reports that big banks were skeptical of doing business with him.

After a string of bankruptcies in his casino and hotel businesses in the 1990s, Mr. Trump became somewhat of an outsider on Wall Street, leaving the giant German bank among the few major financial institutions willing to lend him money.

Now that two-decades-long relationship is coming under scrutiny.

Banking regulators are reviewing hundreds of millions of dollars in loans made to Mr. Trump’s businesses through Deutsche Bank’s private wealth management unit, which caters to an ultrarich clientele, according to three people briefed on the review who were not authorized to speak publicly. The regulators want to know if the loans might expose the bank to heightened risks.

Separately, Deutsche Bank has been in contact with federal investigators about the Trump accounts, according to two people briefed on the matter. And the bank is expecting to eventually have to provide information to Robert S. Mueller III, the special counsel overseeing the federal investigation into the Trump campaign’s ties to Russia.

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It was not clear what information the bank might ultimately provide. Generally, the bank is seen as central to understanding Mr. Trump’s finances since it is the only major financial institution that continues to conduct sizable business with him. Deutsche Bank has also lent money to Jared Kushner, the president’s son-in-law and senior adviser, and to his family real estate business.

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Donald J. Trump in 1996 at the Taj Mahal casino in Atlantic City. Two years later, he began a banking relationship with Deutsche Bank. Credit Chester Higgins Jr./The New York Times

Although Deutsche Bank recently landed in legal trouble for laundering money for Russian entities — paying more than $600 million in penalties to New York and British regulators — there is no indication of a Russian connection to Mr. Trump’s loans or accounts at Deutsche Bank, people briefed on the matter said. The bank, which declined to comment, scrutinizes its accounts for problematic ties as part of so-called “know your customer” banking rules and other requirements.

And with one of its most famous clients headed to the White House, the bank designed a plan for overseeing the accounts of Mr. Trump and Mr. Kushner and presented it to regulators at the New York State Department of Financial Services early this year. The plan essentially called for monitoring the accounts for red flags such as exceptionally favorable loan terms or unusual partners.

Additionally, the New York regulators recently requested information related to the hundreds of millions in loans Deutsche Bank’s private wealth management division provided Mr. Trump, one of the people said, paying particular attention to personal guarantees he made to obtain the loans. Those guarantees have declined as the loans were paid down and the property values increased, but it remains a source of interest to the regulators.

While there is no formal investigation of the bank — and personal guarantees are often required when people receive big loans from their wealth managers — the New York regulators have questioned whether the guarantee could create problems for Deutsche Bank should Mr. Trump fail to pay his debts. To collect, the bank would either have to sue the president, or risk being seen as cutting him a special deal.

It is not a hypothetical concern: Mr. Trump sued the bank in 2008 to delay paying back an earlier loan.

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Deutsche Bank expects it must eventually provide information to Robert S. Mueller III, the special counsel overseeing the federal investigation into the Trump campaign’s ties to Russia. Credit Saul Loeb/Agence France-Presse — Getty Images

Mr. Trump has had a complicated relationship with the bank over the past 20 years, which has included more than $4 billion in loan commitments and potential bond offerings, a majority of which were completed, according to a New York Times review of securities filings and interviews with people with knowledge of the deals. Despite all the risk-taking — and a brief loan default that spurred the 2008 litigation — Mr. Trump’s business has made the bank money, the people said.

A spokesman for the New York regulators declined to comment, and the White House did not respond to requests for comment.

A few years after Mr. Trump sued the bank in 2008, he moved his business from the bank’s commercial real estate lending division to its private wealth division, where executives were more willing to deal with him, according to the people briefed on the matter.

In the past six years, the private wealth unit helped finance three of Mr. Trump’s properties, including a golf course near Miami and a hotel in Washington, according to Mr. Trump’s most recent financial disclosures and the people with knowledge of the loans.

The size of the loans — totaling about $300 million — is somewhat unusual by Wall Street standards, according to former and current Deutsche Bank executives and wealth managers at other Wall Street firms.

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The Trump National Doral resort in Miami. Credit Ilana Panich-Linsman for The New York Times

While it is not unheard-of for real estate developers to obtain large wealth management loans for projects deemed too risky for an investment bank, it differs from bank to bank, and those that do issue loans of that size typically do so for top clients known to pay their bills.

Mr. Trump’s wealth manager at Deutsche Bank, Rosemary Vrablic, has specialized in real estate lending and is known for taking risks on clients, two of the executives and wealth managers said. And her relationship with Mr. Trump is close enough that Ms. Vrablic attended Mr. Trump’s inauguration, according to a person who attended.

Mr. Kushner has established his own relationship with the bank. He and his mother have an unsecured line of credit from Deutsche Bank, valued at up to $25 million, and the family business he ran until January, Kushner Companies, received a $285 million loan from Deutsche Bank last year.

Mr. Kushner’s dealings at the bank have included Ms. Vrablic. In 2013, he ordered up a glowing profile of her in the real estate magazine he owned, The Mortgage Observer, according to a person with knowledge of the matter. The piece concluded with a disclaimer that her “past clients” included Mr. Kushner.

In an interview with The Times last year, Mr. Trump suggested reporters speak with Ms. Vrablic about his banking relationships.

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Trump International Hotel in Washington. Credit Al Drago/The New York Times

“Why don’t you call the head of Deutsche Bank? Her name is Rosemary Vrablic,” he said. “She is the boss.”

A Relationship Is Born

It was 1998, and Mike Offit, fresh off the trading floor of Goldman Sachs for a new job at Deutsche Bank, was hired to put Deutsche Bank’s real estate lending business on the map. To do that, Mr. Offit knew he had to snag big name developers.

That moment arrived when Rob Horowitz, with the real estate firm Cooper-Horowitz, approached him with an idea: Would he work with Mr. Trump, who at the time had a tarnished reputation after several of his casinos landed in bankruptcy?

“My reaction was, why wouldn’t I?” Mr. Offit recalled in a recent interview.

To Mr. Offit, there was little downside to hearing Mr. Trump’s pitch. A short time later, Mr. Trump came by Mr. Offit’s Midtown Manhattan office to discuss a loan for renovations at his 40 Wall Street building. Unlike other developers who arrived with their entourages, Mr. Trump showed up alone, Mr. Offit said, and despite a reputation for bluster, he knew the financials of the deal cold.

“There was some resistance from management because of Donald’s reputation, but I told them that our loan would be wildly overly collateralized even in the worst-case scenario,” Mr. Offit said.

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Rosemary Vrablic of Deutsche Bank helped facilitate loans to Mr. Trump. Credit Michael Nagle

More deals followed. Later in the year, Mr. Trump needed $300 million to build Trump World Tower near the United Nations. But he required a construction loan, which, at the time, Deutsche did not have the right staff to manage. Determined to get the deal nonetheless, Mr. Offit found another German bank to make the loan with the commitment that Deutsche Bank would take possession once the building was constructed.

But as the deal was being finalized, the other German bank had second thoughts because of worries of a labor strike. Just as the deal seemed to be falling apart, Mr. Trump produced a signed commitment from all the major construction unions promising not to strike.

“We were all amazed he managed to get that,” said Mr. Offit, who retired from the bank in 1999.

In the mid 2000s, Mr. Trump was in need of another construction loan. But this time, the loan — up to $640 million to build Trump International Hotel and Tower in Chicago — did not go as well.

A few years after the project began, the 2008 financial crisis upended the global economy and Mr. Trump fell behind on loan payments. According to a person briefed on the deal, Deutsche Bank was discussing a possible extension, when Mr. Trump sued it to avoid paying $40 million that he had personally guaranteed.

His argument, as detailed in a letter to the bank, was novel: “Deutsche Bank is one of the banks primarily responsible for the economic dysfunction we are currently facing,” Mr. Trump wrote.

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Trump International Hotel and Tower in Chicago. Credit Nathan Weber for The New York Times

With the help of a lawyer — Steven Schlesinger of Garden City, N.Y. — Mr. Trump argued that the financial crisis allowed him to invoke the extraordinary event clause in his contract with the bank. Mr. Trump argued Deutsche Bank should pay him $3 billion in damages.

The bank filed its own action against Mr. Trump, demanding he make good on the loan. In a legal filing, Deutsche Bank, which had distributed the loan to a number of other banks, called the lawsuit “classic Trump.”

The standoff culminated with a meeting in Trump Tower, Mr. Schlesinger said.

At the meeting, Mr. Trump threatened to remove his name from the building if he did not get more time to pay. That move, Mr. Trump suggested, would reduce the value of the building.

Ultimately, the bank granted Mr. Trump additional time to repay. And when he did, it was through the Wall Street equivalent of borrowing from one parent to repay the other.

Mr. Trump received a loan from Deutsche Bank’s wealth management unit to pay off the debt he owed the bank’s real estate lending division, according to two people briefed on the transaction. The wealth management unit later issued another loan for the Chicago project that is valued at $25 million to $50 million.