What building was built earlier,  Manhattan Life Insurance Building or 15 Penn Plaza?
Manhattan Life Insurance Building The Manhattan Life Insurance Building was a 348 ft tower at 64-66 Broadway in New York City completed in 1894 to the designs of the architects of Kimball & Thompson and slightly extended north in 1904 making its new address 64-70 Broadway. It was the first skyscraper to pass 100 m in Manhattan.
United Charities Building The United Charities Building, also known as United Charities Building Complex, at 105 East 22nd Street or 287 Park Avenue South, in the Gramercy Park neighborhood of Manhattan, New York City, near the border of the Flatiron District, was built in 1893 by John Stewart Kennedy, a wealthy banker, for the Charity Organization Society.