In this photo from April 13, 1985, work was continuing at the Willard Hotel complex at 14th Street NW and Pennsylvania Avenue NW. (Ray Lustig)

The Willard Hotel was boarded up, vacant and crumbling throughout the 1970s, leaving many to wonder if the Pennsylvania Avenue landmark would ever be restored.

Not so different from another historic building four blocks east today: the Old Post Office Pavilion.

This time, Donald and Ivanka Trump are the developers hoping to turn an extraordinary but dated building into a modern luxury hotel. With the Willard, it was Oliver T. Carr Jr.

The Trumps might be attempting their overhaul in a slow economy with the possibility of a second recession looming, but the economic picture Carr faced in taking on the Willard in 1981 was arguably much worse.

Far from the economic renaissance the District is enjoying today, the city was still rebuilding from the fires that burned in 1968 following the assassination of Martin Luther King Jr., and it had entered a long period of economic and demographic decline.

The differences are so glaring that Carr, still active in Washington real estate but enjoying the summer in Maine, said the Willard and the Old Post Office cannot be compared.

“I think there is absolutely no connection whatsoever,” Carr said of the two projects. “When the Willard was re-done, that part of Pennsylvania Avenue between 15th Street and 7th Street was totally depressed. It was just beginning to come back. The reason that I had faith in it is because we were among the people who had a vision for the downtown, for the West End and for other parts of the city.”

Although the Willard was already known as a famous stopping point for presidents, things were so bad on Pennsylvania Avenue in 1968 that its owner, New York developer Charles B. Benenson, told The Washington Post that he was losing $1,000 a day operating it. He closed it that year and would have torn it down had a lawsuit from historic preservation advocates not prevented it.

Carr said that despite the economic malaise that had spread through the area, he believed real estate between the Capitol and the White House would always carry value. “You had the dumbbell ends. We knew it would be refilled again,” he said.

The federal government stepped in to try to save both properties. In 1972 Congress created the Pennsylvania Avenue Development Corp. to restore the corridor, and the entity acquired the Willard in 1978.

Many years later, it was President Obama and members of Congress who began pushing to redevelop the Old Post Office as part of an effort to take advantage of the nation’s vast real estate holdings to help offset the country’s debt.

Carr, 87, is six years removed from CarrAmerica Realty Corp.’s blockbuster sale of the 26.1 million-square-foot real estate empire he built to private equity firm Blackstone Group for or $5.6 billion. His children operate a number of companies in Washington, including Carr Properties, where Oliver T. Carr III is president and chief executive.

Carr Jr. was already one of the city’s most accomplished developers in 1981 when he stepped in to try to resuscitate the Willard. It had been vacant for 13 years, and banks had walked away from earlier offers to finance a restoration.

Carr said he would restore it into an iconic Washington hotel, much as Trump has said he will do with the Old Post Office. If his experience transforming an antiquated Pennsylvania Avenue property into a high-end attraction is any illustration, the Trumps have a long and trying road ahead.

Over the next five years, with interest rates surging and downtown real estate stagnating, Carr changed his financial partner, hotel operator and architect. Costs skyrocketed. To make the project more financially viable, Carr shuffled plans dramatically, reducing the number of hotel rooms from 600 to under 376 and adding 218,000 square feet of office space.

Eventually Intercontinental Hotel Corp. joined as an operator, and Carr secured financing for a $110 million overhaul, allowing the building to reopen in 1986. Today, most rooms at the Willard InterContinental rent for between $400 and $1,700 a night, though presidential suites can fetch $10,000 on special occasions. Carr keeps his office in the building next door.

He said that many times he has considered trying to redevelop the Old Post Office Pavilion himself, particularly because he said he has an ancestor who helped construct it in the 1890s. He said he believes it is one of a handful of buildings in the District that serve as symbols of the city and the nation to visitors. “For lots of reasons I thought that it should be brought back to life,” he said.

His only advice for Trump is to “do it right and price it right.”

“I wish Mr. Trump the very best in his new undertaking. I think that building’s time has come … Our city should be a welcoming place for the country and the world and that’s one of the signature towers, one of the few that you can see when you are leaving the city and looking back at it.”