On December 15, 2018, about 0933 eastern standard time, a Learjet 35A, N55FN, was substantially damaged when it was involved in an accident during landing at Key West International Airport (EYW), Key West, Florida. The flight was operated by Medway Air Ambulance as a Title 14 Code of Federal Regulations Part 91 positioning flight. According to the operator, the first officer flew the initial approach to runway 9 at EYW. The crew visually acquired the runway but were not in a position to land the airplane and performed a missed approach. During the missed approach, they encountered turbulence, and the captain took the flight controls. While being radar-vectored for the second approach, air traffic control advised the crew that the wind had shifted and was favoring runway 27. The subsequent approach to runway 27 was uneventful. During the landing flare, the crew were unable to arrest the airplane’s descent, and the airplane landed hard. After taxiing to the ramp, they realized that the airplane was damaged during the landing. According to pictures provided by a Federal Aviation Administration (FAA) inspector, the airplane sustained substantial damage to the left engine pylon, left wing, and main landing gear. According to available weather information, a cold front moved across EYW around the time of the accident, followed by a second cold front that was approaching the area. The EYW upper air sounding, launched at 0700, indicated a surface wind from 220º at 6 knots with little directional variation with height and with wind speed increasing with height. At 1,000 ft a low-level wind maximum was identified from 210º at 18 knots, which resulted in a slight risk or "light" low-level wind shear condition below this level and potential surface wind gusts.