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The Brooklyn-Queens Expressway
First of all, everyone should probably stop reading this post right now and go read Robert Caro's The Power Broker and understand all there is to know about how Robert Moses, an unelected official who held an office that had never before wielded significant power, managed to transform the city of New York more than anyone else since the Commissioner's Plan of 1811. One of the biggest achievements (and I use that word loosely) during Moses' tenure, was the construction of the Brooklyn-Queens Expressway. This highway was proposed in the 1930s as a way to ease street traffic and actually make life more bearable for residents of the outer-boroughs. And while, theoretically, easing car congestion is a positive, in practice the BQE only encouraged more car traffic in both Brooklyn and Queens. Beyond that, the BQE was erected in the middle of several vibrant neighborhoods, including Williamsburg, Red Hook, and Windsor Terrace, effectively splitting them apart and ruining the formerly cohesive atmosphere in these parts of Brooklyn. Moses was notoriously cold-hearted about the human cost of his projects, but you can't really say that he didn't get things done or that he didn't change the city. He did. But he did it in a way that was corrosive and detrimental to the city that he claimed to be helping.