The Flatiron Building sits on a scalene right triangle created where Broadway, an old Native American trail, cuts diagonally across Manhattan’s 1811 grid at Fifth Avenue and 22nd and 23rd Streets. In 1857 Amos Eno bought the block for $32,000, built the seven-story Cumberland apartments, and rented its exposed north wall to advertisers, including the New York Times with the city’s first electric sign and a magic lantern that projected election news to huge crowds. By the 1890s the wall earned his family $42,000 a year. After his death, his son William bought the lot for $690,000 in 1899 and flipped it three weeks later, and in 1901 Harry S. Black of the Fuller Company paid about $2 million to build a headquarters there.

Daniel Burnham and Frederick P. Dinkelberg designed a 22-story tower shaped like a classical column, with limestone at the base and terracotta above, while engineer Corydon Purdy built a pre-cut steel frame braced for four times the expected wind. Crowds bet on when it would blow over and called it Burnham’s Folly. It survived, but its downdrafts smashed windows, killed a 13-year-old bicycle messenger in 1903, and lifted women’s skirts. The building went into foreclosure in 1933 and sold for $100,000, then decayed under a deadlocked ownership group until a 2023 court-ordered auction and a plan to convert it to luxury condos by 2026.

• Why the Flatiron was not New York’s first steel-framed skyscraper, and how the 1892 building code made it possible
• Red-hot rivets tossed through the air and a frame that fit together without a single re-drilled hole
• The cowcatcher retail space that developers forced on Burnham against his objections
• Police telling loiterers to skidoo, the local legend behind 23 skidoo
• Jacob Garlick winning the 2023 auction, then failing to pay the deposit and vanishing