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In 2014 and 2015, a Trump legal entity lent at least $96 million to the subsidiary that operated Turnberry, according to British regulatory filings. The next year, the Trump Organization would go back to Deutsche Bank for more.

The relationship between Mr. Trump and Deutsche Bank had survived some rocky moments. In 2008, amid the financial crisis, Mr. Trump stopped repaying a loan to finance the construction of a skyscraper in Chicago — and then sued the bank, accusing it of helping cause the crisis. After that lawsuit, Deutsche Bank’s investment-banking arm severed ties with Mr. Trump.

But by 2010, he was back doing business with Deutsche Bank through its private-banking unit, which catered to some of the world’s wealthiest people. That unit arranged the Doral loans, and another in 2012 tied to the Chicago skyscraper.

Mr. Trump’s go-to in the private bank was Rosemary Vrablic, a senior banker in its New York office. In 2013, she was the subject of a flattering profile in The Mortgage Observer, a real estate magazine owned by Mr. Trump’s son-in-law, Jared Kushner, who was also among her clients. In 2015, she arranged the loan that financed Mr. Trump’s transformation of Washington’s Old Post Office Building into the Trump International Hotel, a few blocks down Pennsylvania Avenue from the White House.

In early 2016, as Mr. Trump was lending tens of millions of dollars to his campaign, his company contacted Ms. Vrablic about getting money for Turnberry, said two of the three people familiar with the request, who spoke on the condition of anonymity because they weren’t authorized to discuss the matter publicly. The proposal was to expand Deutsche Bank’s outstanding loans backed by the Doral by well over $10 million and to use the proceeds for work on Turnberry, the people said.

Around the time that Mr. Trump was winning New Hampshire, South Carolina and Nevada, officials in the private-banking unit informed their superiors that they were inclined to provide him with the loan, according to one of the people familiar with the internal discussions.

Senior executives in New York balked, arguing that Mr. Trump’s candidacy made such a loan unacceptably risky, the three people said. In part, they feared the bank’s reputation could be harmed if the transaction were to become public because of the polarizing statements Mr. Trump was making on the campaign trail.