Donald Trump and his father, Fred Trump, a real estate developer who died in 1999. (Ron Galella/WireImage)

In the fall of 1976, Fred Trump made a rare visit to a housing complex he owned in Seat Pleasant, Md. For months, Prince George’s County inspectors had complained of broken windows, rotted rain gutters and missing fire extinguishers at the 504-unit Gregory Estates. When the problems weren’t fixed, fed-up officials asked Trump to come down and meet in person.

The “meeting,” however, was brief. As soon as the multimillionaire arrived, he was arrested and — to his outrage — briefly jailed.

The incident came at an awkward time for the Trump family. Fred Trump was accused of subjecting black tenants to poor conditions just a year after settling a lawsuit with the federal government, which alleged that the Trump Organization refused to rent to African Americans.

And his hard-charging son was in the middle of an audacious and ultimately unsuccessful bid to construct a $125 million convention center in the nation’s capital. Barely 30 years old, Donald Trump saw opportunity in downtown Washington’s barren lots and riot-scarred buildings near Union Station.

In an interview, Trump told The Washington Post he had no idea his father had been arrested in Prince George’s. But he had no trouble recalling his convention center proposal, which included a luxury hotel in the historic Government Publishing Office.

“It would have been great for Washington,” he said in an email.

Forty years later, Trump has finally gotten his foothold in the capital with the opening last month of his glitzy $212 million Trump International Hotel in the Old Post Office Pavilion. And the Republican presidential nominee is trying to claim an even grander address on Pennsylvania Avenue NW: the White House.

The seeds of his Washington ambitions can be traced to 1976, when his convention center proposal fell victim to his strained relationship with African Americans — something that has re-emerged as he runs for president.

“He doesn’t really reach out to black people properly,” said Joseph Searles III, now 74, an African American former National Football League player who was one of Trump’s partners in the convention center project.

“Every time we went to a community meeting,” Searles said, “he’d piss off too many people, just like he does now.”

‘Get me out of jail’
The Washington Post explores the origins of Donald Trump's transformation from a businessman to political candidate. (McKenna Ewen,Whitney Shefte,Dalton Bennett/The Washington Post)

In the spring of 1961, when Donald Trump was finishing his freshman year at a military high school in New York, his father purchased Gregory Estates from the Federal Housing Administration. Records show he paid $1. “It was bought at a distress sale,” Donald Trump recalled.

The sprawling, three-story apartment complex had been built a decade earlier during the postwar boom. When the developer couldn’t keep up with mortgage payments, the FHA took over, then sold the property to Bruche Realty Corp., one of Fred Trump’s many companies.

Fred Trump rented the one- and two-bedroom apartments for about $150 a month. Initially, his tenants were poor whites. After the 1968 riots devastated parts of Washington, however, both the District and the surrounding areas began to change. African Americans, many of them middle class, moved into Prince George’s County as whites fled to Montgomery County and other suburbs.

By 1970, when Donald Trump began to help manage Gregory Estates, the tenants were predominantly black. With his blond pompadour and Ivy League education, the young Trump stood out in the low-income apartment project. He would fly down for a week at a time and stay in the model unit that was shown to prospective renters.

In his interview with The Washington Post this year, he remembered collecting rent for his father at Gregory Estates.

“That was a dangerous territory,” Trump recalled. “I’d go there sometimes by myself and I’d say, ‘Pop, this is a rough piece of property here.’ ”

Willie Cabbagestalk remembers things differently.

“He didn’t collect s---,” said Cabbage­stalk, 75, who has worked at Gregory Estates, now called Pleasant Homes Apartments, since the mid 1960s. “He gave me orders.”

He agreed with Trump, however, that Gregory Estates rapidly declined in the late 1960s and early 1970s.

“It used to be rough here,” Cabbage­stalk said. “We had 50 to 60 windows broken per day.”


The Pleasant Homes Apartments in Seat Pleasant, Md. Formerly known as Gregory Estates, the complex was once owned by Donald Trump’s father. Fred Trump was arrested and briefly jailed in 1976 for failing to fix housing-code violations. (Sarah L. Voisin/The Washington Post)

By the time inspectors visited in January 1976, Gregory Estates was falling apart.

When the notoriously frugal Fred Trump failed to pay for repairs by that July, his housing license was revoked, preventing him from signing new leases. The blow to his pocketbook spurred him to action: Trump agreed to fly to Maryland to meet with local officials on Sept. 29, 1976.

Instead, he was arrested.

Prince George’s was cracking down on dilapidated housing complexes, but arresting an owner was unusual.

“We probably haven’t issued four arrest warrants in the past five years,” Joseph T. Healey, the county’s housing inspector supervisor, told The Post for an article about the arrest.

Fred Trump was furious. From his cell, the real estate mogul called Seat Pleasant Mayor Henry T. Arrington and demanded he be released.

“Come get me out of jail,” Trump said, according to Arrington.

Arrington, now 84, was well aware of the problems at Gregory Estates — “It was infested with drugs” — but he had never met the landlord.

When the mayor told Trump that he had no jurisdiction over the jail, Trump called New York, arranged payment of his $1,000 bond and flew home immediately.

Irving Eskenazi, a Trump employee, attributed the problems to “a very serious change in the area. Low-income people started moving in.”

Trump, he told The Post at the time, was a “fine gentleman” who “shouldn’t even be going to a project like this.” And county officials should have known better than to “try and louse around with his reputation.”

Donald Trump, who had risen to president of the Trump Organization, vowed to fight the allegations in court. But his father pleaded no contest to five misdemeanor charges and paid a fine of $3,640 — the equivalent of about $15,400 today.

Fred Trump didn’t waste any time washing his hands of the place. Shortly after his arrest, he hired H.R. Crawford, a former assistant secretary of the U.S. Department of Housing and Urban Development, to manage the property. Trump, Crawford said, handed him the keys and severed his ties to Bruche Realty and Gregory Estates.

“He didn’t want to come back to Prince George’s County ever again,” Crawford, 74, recalled.

‘Trump did not excite anybody ’

On July 7, 1976, Donald Trump, then 30, stood beside a model of the D.C. convention center he hoped to build. (Tom Allen/The Washington Post)

On July 7, 1976, Donald Trump stood before D.C. officials and promised to transform the struggling capital with a 1.8 million-square-foot convention center.

“The center will bring in $500 million in new business, and the city will take $45 to $50 million of that in taxes,” the 30-year-old, sharply dressed in a wide-lapelled suit and patterned tie, was quoted by The Post as saying.

For the next year, the young Trump tried to sell the city on his plan. But Trump’s brash personality and off-the-cuff style angered officials and alienated African American residents.

In the summer of 1976, both Washington and Donald Trump were new to negotiating. Trump had first gained notoriety by defending his family’s business against federal allegations of racial bias, ultimately settling the case without admitting fault. Then he bought the old Commodore Hotel in Manhattan and turned it into the Grand Hyatt. He was in the midst of convincing New York City officials to build a convention center on land to which he held a lucrative option when he came to the capital to pitch a similar plan.

Washington had gained home rule on Christmas Eve in 1973. The city’s first elected mayor, Walter Washington, felt that a new convention center near Mount Vernon Square would lift the District’s economy and spirit.

Congress still had to approve the plan, however, and a tense standoff ensued. Lawmakers, led by Sen. Patrick J. Leahy (D-Vt.), criticized the proposal as too costly.

In stepped The Donald.

Trump offered to arrange $125 million in private financing to build a bigger convention center next to Union Station.

Trump wasn’t the only millionaire to offer his services. Abe Pollin, owner of the Washington Bullets and Capitals, initially wanted a convention center alongside a sports arena downtown before settling for an arena in Maryland. Home improvement store magnate John W. Hechinger proposed his lumberyard in Northeast Washington as a site. Architect Arthur Cotton Moore even suggested stringing inflatable “helium cells” over RFK Stadium to create a convention center covered by the “world’s first ‘floating roof.’ ”

City officials were caught off guard by Trump’s plan, the Washington Star reported. He and his partners briefed the mayor only a few days before bringing the idea before the D.C. Redevelopment Land Agency board.

Trump’s surprise proposal came with two catches. Although he would use private financing to build the center — which would stretch from Massachusetts Avenue to I Street and North Capitol Street to Second Street — Trump said he was seeking subsidies to meet “a portion of the debt service and carrying charges,” according to The Post. He said the amount would be “$5 to $10 million at the absolute maximum” and would be more than offset by the taxes the city would rake in.

In a move foreshadowing his return to the District 40 years later, Trump also wanted permission to transform the historic red-brick Government Publishing Office building into a luxury hotel.

But Trump ran into serious headwinds. Unlike in New York, he was relatively unknown in the capital.

Donald J. Trump, already president of the Trump Organization, tried to sell skeptical D.C. officials on a $125 million convention center. (Tom Allen/The Washington Post)

“The name Trump did not excite anybody back then,” said Sterling Tucker, the D.C. Council chairman at the time.

A bigger hurdle was that the city’s first elected officials were against privately financing the convention center. “We were trying to control our destiny,” recalled Tucker, now 92.

What ultimately killed Trump’s $125 million plan, however, was a public school.

After Trump’s July 7 presentation, he was told that he would have to wait while the redevelopment board considered the proposal, including concerns raised by community groups.

“This is ridiculous. That’s why Washington doesn’t have a convention center,” Trump responded, according to the Star.

When the redevelopment board met again two weeks later, about 50 residents showed up to protest the location of Trump’s proposed convention center. Much of the land was already promised to other things, including Perry Simmons Elementary, they argued.

When the board rejected Trump’s plan, they cheered.

Three years later, the city began construction on the Washington Convention Center near Mount Vernon Square. Smaller than Trump’s proposal, it opened in 1983 but was quickly dwarfed by competitors. It was demolished in 2004.

In an email, Trump said he remembered his convention center idea well, although he “didn’t pursue it heavily.”

“The project we are opening now is even more exciting,” he added.

Trump’s palatial new hotel on Pennsylvania Avenue NW will hold its formal grand opening just days before the election. He cited it during his second debate with Hillary Clinton as an example of his business acumen, touting the work as “under budget, ahead of schedule, saved tremendous money.”

The project has also drawn protests. Dozens gathered outside on Trump International’s first day of operation, chanting, “No Trump, no KKK, no racist USA!” Two weeks ago, a man spray-painted “Black Lives Matter” on its entrance. On Thursday, labor activists picketed over stymied efforts to organize workers at a Trump hotel in Las Vegas.

“Donald Trump,” they shouted, “has got to go.”


Chanting, "Hey, hey, ho, ho, Donald Trump has got to go," union workers picket outside the Trump International Hotel over a labor dispute at a Trump property in Las Vegas. (Nikki Kahn/The Washington Post)

Alice Crites and Karen DeYoung contributed to this report.