She seemed like the model tenant. A 33-year-old nurse who was living at the Y.W.C.A. in Harlem, she had come to rent a one-bedroom at the still-unfinished Wilshire Apartments in the Jamaica Estates neighborhood of Queens. She filled out what the rental agent remembers as a “beautiful application.” She did not even want to look at the unit.
There was just one hitch: Maxine Brown was black.
Stanley Leibowitz, the rental agent, talked to his boss, Fred C. Trump.
“I asked him what to do and he says, ‘Take the application and put it in a drawer and leave it there,’” Mr. Leibowitz, now 88, recalled in an interview.
It was late 1963 — just months before President Lyndon B. Johnson signed the landmark Civil Rights Act — and the tall, mustachioed Fred Trump was approaching the apex of his building career. He was about to complete the jewel in the crown of his middle-class housing empire: seven 23-story towers, called Trump Village, spread across nearly 40 acres in Coney Island.
He was also grooming his heir. His son Donald, 17, would soon enroll at Fordham University in the Bronx, living at his parents’ home in Queens and spending much of his free time touring construction sites in his father’s Cadillac, driven by a black chauffeur.
“His father was his idol,” Mr. Leibowitz recalled. “Anytime he would come into the building, Donald would be by his side.”
Over the next decade, as Donald J. Trump assumed an increasingly prominent role in the business, the company’s practice of turning away potential black tenants was painstakingly documented by activists and organizations that viewed equal housing as the next frontier in the civil rights struggle.
The Justice Department undertook its own investigation and, in 1973, sued Trump Management for discriminating against blacks. Both Fred Trump, the company’s chairman, and Donald Trump, its president, were named as defendants. It was front-page news, and for Donald, amounted to his debut in the public eye.
“Absolutely ridiculous,” he was quoted as saying of the government’s allegations.
Document: Affidavit of Donald Trump in 1973 About the Housing Bias Case
Looking back, Mr. Trump’s response to the lawsuit can be seen as presaging his handling of subsequent challenges, in business and in politics. Rather than quietly trying to settle — as another New York developer had done a couple of years earlier — he turned the lawsuit into a protracted battle, complete with angry denials, character assassination, charges that the government was trying to force him to rent to “welfare recipients” and a $100 million countersuit accusing the Justice Department of defamation.
When it was over, Mr. Trump declared victory, emphasizing that the consent decree he ultimately signed did not include an admission of guilt.
But an investigation by The New York Times — drawing on decades-old files from the New York City Commission on Human Rights, internal Justice Department records, court documents and interviews with tenants, civil rights activists and prosecutors — uncovered a long history of racial bias at his family’s properties, in New York and beyond.
That history has taken on fresh relevance with Mr. Trump arguing that black voters should support him over Hillary Clinton, whom he has called a bigot.
While there is no evidence that Mr. Trump personally set the rental policies at his father’s properties, he was on hand while they were in place, working out of a cubicle in Trump Management’s Brooklyn offices as early as the summer of 1968.
Then and now, Mr. Trump has steadfastly denied any awareness of any discrimination at Trump properties. While Mr. Trump declined to be interviewed for this article, his general counsel, Alan Garten, said in a statement that there was “no merit to the allegations.” And there has been no suggestion of racial bias toward prospective residents in the luxury housing that Mr. Trump focused on as his career took off in Manhattan in the 1980s.
In the past, Mr. Trump has treated the case as a footnote in the narrative of his career. In his memoir “The Art of the Deal,” he dispensed with it in five paragraphs. And while stumping in Ohio, he even singled out his work at one of his father’s properties in Cincinnati, omitting that, at the time, the development was the subject of a separate discrimination lawsuit — one that included claims of racial slurs uttered by a manager whom Mr. Trump had personally praised.
As eager as he was to leave behind the working-class precincts of New York City where Fred Trump had made his fortune, Donald Trump often speaks admiringly of him, recalling what he learned at his father’s side when the Trump name was synonymous with utilitarian housing, not yet with luxury, celebrity, or a polarizing brand of politics.
“My legacy has its roots in my father’s legacy,” he said last year.
Coming Under Scrutiny
Fred Trump got into the housing business when he was in his early 20s, building a single-family home for a neighbor in Queens. During World War II, he constructed housing for shipyard workers and Navy personnel in Norfolk, Va. After the war, he returned to New York, setting his sights on bigger, more ambitious projects, realized with the help of federal government loans.
His establishment as one of the city’s biggest developers was hardly free of controversy: The Senate Banking Committee subpoenaed him in 1954 during an investigation into profiteering off federal housing loans. Under oath, he acknowledged that he had wildly overstated the costs of a development to obtain a larger mortgage from the government.
In 1966, as the investigative journalist Wayne Barrett detailed in “Trump: The Greatest Show on Earth,” a New York legislative committee accused Fred Trump of using state money earmarked for middle-income housing to build a shopping center instead. One lawmaker called Mr. Trump “greedy and grasping.”