Glass half-full;
Grand Hyatt Hotel
Trump bought the former Commodore Hotel, which had fallen into relative disrepair, from Penn Central Railroad in 1974 and after six years of construction, the Grand Hyatt Hotel debuted. Smack dab in the heart of New York City, with the image of Grand Central reflected off its glass façade, the 34-story hotel is still booming business today.
Trump Tower
Trump broke ground on his now-famous 48-story Trump Tower in 1980. The luxury high-rise opened in 1983 and, with upscale restaurants and stores located in the mostly residential building, is still highly sought after real estate.
Wollman Rink
Trump renovated Wollman Rink in 1986 after contacting Mayor Ed Koch and offering to complete the renovation for $3 million. He finished the project on time and $750,000 under budget. Wollman Rink remains a Central Park fixture with more than 5 million annual visitors.
40 Wall Street
Trump purchased the building in 1995 for $1 million and renovated it for $35 million. Today, 40 Wall Street, one of the tallest office buildings in downtown New York, is worth over $500 million.
Trump Place
After years of negotiations, Trump finally broke ground on Trump Place, the gargantuan housing development along the Hudson River. The development includes 25 acres of open space and 5,700 apartments housed in 18 residential buildings.
The Apprentice
The Apprentice premiered on NBC in 2004 to great ratings. Trump served as not only the host but also the executive producer, raking in $1 million per episode. The show was successful enough that it inspired a spinoff, The Celebrity Apprentice.