In 1945 a B-25 Mitchell bomber crashed into the side of the Empire State Building.
The accident didn't compromise the building's integrity but damaged floors 78 to 80.
However, fourteen deaths were recorded.
Damage estimated at $14 million in 2018.
On Saturday, July 28, 1945, Lieut. Col. William F. Smith Jr. was piloting a B-25 Mitchell bomber on a routine personnel transport mission from Bedford Army Air Field in Massachusetts to Newark Airport in New Jersey.
At 9:40 a.m., the aircraft crashed into the north side of the building carving an 18-by-20-foot (5.5 m × 6.1 m) hole where the offices of the National Catholic Welfare Council were located.
One engine shot through the Southside opposite the impact and flew as far as the next block, dropping 900 feet (270 m) and landing on the roof of a nearby building and starting a fire that destroyed a penthouse art studio.