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Donald Trump's Best and Worst Gambles

Photo Credit: Pascal Walschots

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Grand Hyatt Hotel

In 1974, Trump brokered a deal with Penn Central Railroad to purchase one of their distressed assets, the Commodore Hotel. He paid $130 million to buy and renovate the hotel.

After six years of construction, the hotel reopened in November, 1980, as the Grand Hyatt. One of Trump's better gambles, the 34-story building featured a new fa├žade of shimmering glass, reflecting the image of Grand Central Terminal next door.

Photo Credit: Pascal Walschots