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Who piloted the first F-14?
Short answer
Two Grumman test pilots: chief test pilot Robert K. Smyth and project test pilot William Miller. They flew the first F-14A, BuNo 157980, on its maiden flight from Calverton on 21 December 1970. Bad weather forced them to cut that flight short.

The first Tomcat's crew
Those who flew the first F-14 were Grumman's chief test pilot, Robert K. Smyth, and the project test pilot, William Miller. On 21 December 1970, the first full-scale development (FSD) F-14A, Navy BuNo 157980, took off for its maiden flight from Grumman's flight test center at Calverton. Bad weather forced the test pilots to cut the flight short. That was the date of the F-14's first flight.
The second flight, with Miller up front
On 30 December the same aircraft flew again, and that day Miller took the front cockpit. A chase aircraft warned that the Tomcat was leaving a trail of smoke, and shortly afterward the F-14 suffered a failure of its primary hydraulic system.
How that flight ended
The failure originated in a fatigue failure of the two main titanium hydraulic lines, caused by pump resonance coinciding with a loose fitting. The pilot lost all control of the aircraft, and the crew was forced to eject. Both suffered only minor injuries.
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