Ed Koch

In addition to thinking he could own the Empire State Building and build the tallest building in the world, Donald Trump also had a pipedream of single-handedly repairing the Williamsburg Bridge in 1988. Yesterday, Gothamist's Editorial Director Jen Carlson tweeted a series of stories from the time detailing how the Donald presented the city with a proposition to get the necessary repairs (the then-85-year-old bridge was closed due to cracked and corroded beams) done quicker and cheaper. According to the Associated Press, "Trump said the deal could work the same way as [Central Park's Wollman Rink] construction in 1986 - he would advance the money, get the job done and be reimbursed for costs."
So how'd he screw this one up?