EPISODE 299: Part Two of our series on the history of Brooklyn Heights, one of New York City's oldest neighborhoods.

By the 1880s, Brooklyn Heights had evolved from America's first suburb into the City of Brooklyn's most exclusive neighborhood, a tree-lined destination of fine architecture and glorious institutions.

The Heights would go on a roller-coaster ride with the opening of the Brooklyn Bridge and the transformation of Brooklyn into a borough of Greater New York. The old-money wealthy classes would leave, and the stately homes would be carved into multi-family dwellings and boarding houses.

The new subway would bring the bohemians of Greenwich Village into Brooklyn Heights, transforming it into an artist enclave for most of the century. But even with addition of trendy hotels and the Brooklyn Dodgers (whose front office was located here), the Heights faced an uncertain future.

When Robert Moses began planning his Brooklyn Queens Expressway in the 1940s, he planned a route that would sever Brooklyn Heights and obliterate many of its most spectacular homes. It would take a devoted community and some very clever ideas to re-route that highway and cover it with something extraordinary -- a Promenade, allowing all New Yorkers to enjoy the exceptional views of New York Harbor.

This drama only served to highlight the value and unique nature of Brooklyn Heights and its extraordinary architecture, leading New York to designate the former tranquil suburb on a plateau into the city's first historic district.

FEATURING: Truman Capote, Jackie Robinson, Gypsy Rose Lee, St. Ann's Warehouse, Matt Damon and the Jehovah's Witnesses!

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George Robson - Partner at Sequoia Capital