Donald immediately sought out building projects that were larger and carried higher profiles than his father’s outer-borough apartment blocks. Fred was reluctant at first but eventually backed Donald’s projects in the heart of the Big Apple.
Donald used the tools and tricks that he’d learned at his father’s side, having inherited Fred's eye for distressed real-estate gems. And with the entirety of New York City sliding toward bankruptcy in the early 70s, there were more than a few such gems for the having.
Trump’s biggest early deal was rescuing the once-grand Commodore Hotel from bankruptcy and transforming it into the Grand Hyatt. He opened the refurbished hotel in 1980, with the help of a 40-year tax abatement from the City of New York.
In 1983, Trump put his stamp on the city with his 68-story Trump Tower in midtown Manhattan. The mixed-use skyscraper featured the black glass surfaces and brass trimmings that would mark all too many of his later buildings. The building captured the aesthetic of many baby boomers who were coming into money for the first time during the economic boom of the 1980s.
His building projects and persona placed Trump squarely in the public eye. And in 1987, he capitalized on his newfound fame with a business book entitled “The Art of the Deal,” which spent 52-weeks on bestseller lists.
Flush with success, Trump moved into the gaming business, buying the Taj Mahal Casino. But the move proved one gamble too many, and by 1989 Trump was in more debt than he could make the payments on. He kept afloat by taking on more loans until 1991. With bankruptcy looming, Trump’s creditors agreed to restructure his debt, taking half-ownership of the casino. The agreement also forced Trump to sell his airline, the Trump Shuttle airline, and his 282-foot Trump Princess yacht.
From this nadir, Trump gradually restored The Trump Organization’s finances. One of the deals that helped him do so involved 40 Wall Street, a 70-story tower in downtown Manhattan, originally known as the Bank of Manhattan Trust building. Trump bought the building for between $1 million and $10 million in 1995 and renovated it. He would later take out a $160 million mortgage on the building to finance other investments. By 2006, Forbes put a $260 million price tag on the property.
In 1999, when patriarch Fred Trump died, he left behind a handsome estate valued at $250-$300 million. However, the exact amount Donald Trump inherited is unknown.
As the century turned, Donald Trump continued to buy and construct Manhattan real estate. In 2001, he completed the 72-story Trump World Tower, across the avenue from the United Nations building, and began construction on Trump Place, a series of luxury high-rises along the Hudson River.
Another bold move that paid off was Trump’s $73-million purchase of the Chicago Sun-Times building. In its place, he planned to build the tallest building in the world, Trump International Tower, Chicago. But the September 11, 2001, terrorist attacks convinced him to scale back, ultimately building the second-tallest tower in Chicago. Since it opened in 2009, the tower has been a success.
Trump’s career as a public figure, which had shrunk significantly following his near-bankruptcy in the early 90s was revived after he hosted a reality TV show called "The Apprentice" in 2003. The NBC show, in which contestants vied for a management job in one of Trump's companies, was a big hit.