The 1935 Labor Day Hurricane was a compact intense tropical cyclone (TC) that passed over the central Florida Keys on the 2nd of September in 1935 (Labor Day that year), before tropical cyclones were given names. It had very low atmospheric pressure in the eye (center) of the storm, and very high wind velocities surrounding the eye.
An evacuation train was late, and the storm surge killed hundreds of people who were waiting to be evacuated, including World War I verterans at road-building work camps. The railroad could not afford to fix the resulting storm damage, went bankrupt, and was sold to the state to be converted into the road highway across the Keys.
Damage of the storm was amplified by poorly designed transportation infrastructure that persists today and will amplify damage of future storms.
The Labor Day Hurricane of 1935 tracked toward the United States north of Cuba, turned northward, bisecting the Florida Keys, crossed into the Gulf of Mexico (GOM), northern Florida and Atlantic US states, then back out to the Atlantic Ocean, becoming extratropical near Greenland.
This storm (ranked Category 5+), and Hurricane Donna in 1960 (ranked Category 4), are the last major tropical cyclones with eye of the storm to pass over the Central Keys. In the timescale of hurricanes, that was not very long ago, and more storms like those are likely in the future.