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Donald Trump's Best and Worst Gambles

Photo Credit: Getty Images

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Wollman Rink

In May 1986, Trump criticized New York City’s ongoing efforts to renovate Wollman Rink, a popular ice skating spot in Central Park. Disgusted by the city’s inefficient use of time and resources, he contacted Mayor Ed Koch and offered to complete the renovation for $3 million dollars.

Initially, Koch balked, but after the media ran the story, the mayor agreed to let Trump take the reins.

Construction began in July, 1986. Four months later, Trump finished the project on time and $750,000 under budget. On Nov. 13, 1986, with standard Trump fanfare, Wollman Rink reopened and remains one of Trump's key contributions to the city.

Photo Credit: Getty Images