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.
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 three 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.
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 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.
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.