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The New York Life Building is a 1928 building by Cass Gilbert, the designer of the Woolworth Tower; the rooftop pyramid is a trademark of his. Built on site of New York, New Haven & Hartford Depot, which in 1871 became P.T. Barnum's Hippodrome, later Gilmore's Garden, which the Vanderbilt family turned into the original Madison Square Garden.

This was torn down and rebuilt in 1890 to a design by Stanford White and is considered his masterwork. Topped by Augustus Saint-Gaudens' Diana (now in Philadelphia Museum of Art; a smaller copy is at the Met). In 1906, White was shot and killed in his building's Roof Garden by Harry K. Thaw, jealous husband of White's former mistress Evelyn Nesbit.

In 1900, the Garden was the site of the first U.S. auto show. In 1913, it hosted the Patterson Strike Pageant, organized by Mabel Dodge and Big Bill Haywood, directed by John Reed with scenery painted by John Sloan. The longest Democratic convention in history was held here in 1924, selecting John Davis after 17 days.