Gregory Rockwood was one of the crew members awarded the 2004 Mackay Trophy for the "most meritorious flight of the year" by an Air Force person, persons or organization. Jolly 11 and Jolly 12 crew members distinguished themselves by gallantry in connection with rescue operations near Kharbut, Iraq, on April 16, 2004. While supporting of Operation Iraqi Freedom, Jolly 11 Flight launched to rescue a five-person crew of a U.S. Army CH-47 Chinook helicopter that crashed in a sandstorm with near zero visibility. En route to the crash scene, crews realized their forward looking infra-red and night vision goggles were ineffective. Despite this handicap, the crew of Jolly 11 was able to locate the survivors. Both aircraft then made near zero visibility approaches relying nearly exclusively on the flight engineers' and aerial gunners' inputs for precision navigation. Following the successful survivor contacts and recovery by the Flight's Pararescuemen, Jolly 11 and Jolly 12 were individually engaged by separate multiple surface-to-air missiles attacks. Using evasive maneuvers, Jolly 11 evaded two missiles. Jolly 11 and Jolly 12 continued to provide support with defensive fire until the formation was clear of the threat area, saving the lives of five U.S. Army personnel.

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