Brooklyn approach to the Brooklyn-Battery Tunnel, 1950.

Conceived in the late 1930s by city officials, this project was one that master planner Robert Moses was actually not a proponent (and complained about the resulting tunnel for decades). Moses wanted to construct a bridge between lower Manhattan and Brooklyn but city officials, including Mayor LaGuardia, and President Roosevelt advocated for the tunnel (with FDR citing issues of national security in the construction of a bridge as well as his dislike for Moses).

Construction on the tunnel began in 1940, with FDR attending the groundbreaking ceremony, but was waylaid by World War II. Completed and opened to traffic in 1950 it is the longest continuous underwater road in North America. In 2010 it was renamed (officially, though not colloquially) the Hugh L. Carey Tunnel, for the former New York State Governor.