Clemente was 38 years old and one of the greatest baseball players who ever lived. He had won two World Series championships with the Pittsburgh Pirates. On September 30, 1972, in his final at-bat of the regular season, he became only the 11th player in Major League Baseball history to collect 3,000 hits. In October, he traveled to Managua to coach the Puerto Rico national baseball team at the 1972 Amateur World Series. He was there when the 6.3-magnitude earthquake struck on December 23, and he threw himself into relief work, using his own money and his public visibility to organize aid shipments. Local television host Luis Vigoreaux helped convince him to deepen his involvement. When Clemente learned that relief supplies were being diverted, he chartered a fourth plane, determined to confront the situation personally.

The aircraft was a Douglas DC-7CF, a 1957 freighter conversion leased for $4,000 from American Air Express Leasing Company, owned by a 27-year-old Puerto Rican named Arthur S. Rivera. What Clemente did not know was that the plane had suffered a taxiway accident just 29 days earlier, damaging the propeller blades on engines No. 2 and No. 3 and the engine cooler scoop on No. 3. The standard procedure after a sudden engine stoppage is to disassemble the engine and inspect its parts for cracks using magnetic particle inspection. This was not done. Rivera pressed his mechanics to keep the engines in service. An FAA inspector checked the propeller shaft tolerances and found them within limits, though a later report suggested he had merely witnessed the inspection rather than conducting it. The DC-7 was powered by Wright R-3350 engines, a design with a troubled history of overheating and detonation problems dating back to their rushed wartime production.

The flight had already been aborted once that evening for mechanical problems. On the dark, moonless night of December 31, after additional work on the engines, Captain Jerry Hill taxied to runway 7 at Isla Verde International Airport. The weather had cleared: 10-mile visibility, only scattered clouds. At 9:20 p.m., the plane was cleared for takeoff. It used an exceptionally long takeoff roll and gained very little altitude. Hill began a left turn to the north. At 9:23 p.m., the San Juan tower received a single transmission: "N500AE coming back around." Moments later, engine No. 2 failed catastrophically, and engine No. 3 likely lost power as well. These two engines, closest to the fuselage, contained the hydraulic pumps. Without them, the pilot would have been forced to rely on a manual backup control system while attempting to ditch into the ocean on a night with no moonlight and no visible horizon. The plane descended into the Atlantic approximately 1.5 miles offshore.

Recovery efforts began immediately. By 11 p.m., radio and television stations across Puerto Rico were broadcasting news of the crash, and crowds gathered at Pinones Beach to help search. Of the five people on board, only Captain Hill's body was recovered. The wreckage was not located until January 4, 1973, scattered across approximately four acres of ocean floor. Both wings had separated from the fuselage. The cockpit was destroyed. All four engines were accounted for, but none remained attached to the wings. The NTSB attributed the crash to engine damage from the earlier taxiway accident that was never properly repaired, compounded by lean detonation, excessive engine wear, an uncertified co-pilot, an uncertified flight engineer, and overloading. The crash site was listed on the National Register of Historic Places in 2022. It is, so far as such designations go, a memorial to five people who died trying to help strangers and to the cascade of maintenance failures, cost-cutting, and inadequate oversight that put them on a plane unfit to fly.