He later left the Army, and was accepted into the United States Marine Corps Reserve as an aviation cadet on February 18, 1936. He received his "Wings of Gold" as a Naval Aviator on March 11, 1937 and his Marine officer's commission.
Boyington resigned his commission on August 26, 1941 to join the quasi-military 1st American Volunteer Group being formed by the Central Aircraft Manufacturing Company for war service in Asia along side the China Air Force: the famous "Flying Tigers". Boyington flew with the Flying Tigers into the spring of 1942, by which he had been credited with 3.5 aerial victories (3 kills, 1 assist) when he broke his contract to return to the United States.
His wartime service wasn't done though, not by a long shot.
In August 1943, Boyington, then without a squadron, gathered together 27 fellow pilots - some combat veterans, some new trainees - all without assignments and got permission to form a new unit as its commander. They were designated as the second incarnation of Marine Fighting Squadron 214 (VMF-214). Boyington's new command gathered shot-up Vought F4U Corsair fighters no longer wanted by other units and got them back into service.
The aviators of VMF-214 wanted to nickname themselves to establish their "unwanted" status. The first suggestion was "Boyington's Bastards", but that was ruled out by the chain of command as being inappropriate. They then decided they'd go to war as the "Black Sheep", meaning more or less the same thing.
At age 31, Major Boyington was by far the oldest man in the squadron. His Marines began calling him "Gramps", which became the nickname "Pappy" by which he was eventually known.
After just four weeks of stand-up, the "Black Sheep" started fighting in the skies of the Solomon Islands and New Guinea campaigns on September 12, 1943. For the next 84 days, they became one of the most tenacious, combat-successful fighting units in aviation history.
VMF-214 was credited with the destruction of 203 enemy aircraft, including 97 air-to-air kills and producing nine "aces" (five or more aerial victories). They also sank multiple Japanese ships and were relentless in attacking ground targets as well.
The "Black Sheep" were famous for circling Japanese air bases, taunting the enemy into coming up into the skies to challenge them. One such occurrence of that tactic over Kahili on October 27, 1943 saw VMF-214 shoot down 20 of the enemy without a single loss.
On January 3, 1944, during an attack on Rabaul, the "Black Sheep" found themselves fighting against insurmountable odds versus a larger Japanese force. During that day's battle, Boyington shot down his 26th enemy aircraft of the war, tying the record for kills by a single American pilot, but his own plane succumbed to enemy fires. His fate was unknown, and he was listed as missing in action.
In actuality, Boyington survived being shot down and was captured by the Japanese. His capture was never reported to the International Red Cross, as it should have been, and unbeknownst to the United States, he spent the next 20 months until war's end as a prisoner of war. He was freed from the Omori Prison Camp in Japan on August 29, 1945, just four days before Japan's official surrender on September 2.
Upon his liberation and return to the United States, Pappy Boyington learned that in absentia he had been promoted to Lieutenant Colonel and that for his indomitable courage in command of the "Black Sheep", he had already been awarded the two highest decorations he could have been: the Medal of Honor for the period September 12, 1943 to January 3, 1944 and the Navy Cross specifically for the day he was shot down, January 3, 1944.
His Navy Cross was presented to him by General Alexander Vandegrift, Commandant of the Marine Corps and himself a combined Medal of Honor and Navy Cross recipient, on October 4, 1945. The next day, Pappy Boyington received the Medal of Honor from President Harry S. Truman at the White House.
At his death on January 11, 1988 at age 75 in Fresno, California, his passing was honored by a flyby of the "Black Sheep" there before his remains were transported to Arlington National Cemetery where he today rests in peace.
The "Black Sheep" still fly today. The squadron is now known as Marine Attack Squadron 214 (VMA-214) and they fly the McDonnell Douglas AV-8B Harrier II from their home base of Marine Corps Air Station Yuma in Arizona. The squadron is part of Marine Aircraft Group 13, 3rd Marine Aircraft Wing, I Marine Expeditionary Force.
In tribute to their sister service's greatest heroes, the United States Navy has often named warships for Marine Medal of Honor recipients. Shockingly, there has never been a vessel named for Colonel Boyington. It would well behoove the Secretary of the Navy to be mindful of that as he decides the names for future Arleigh Burke-class destroyers or Freedom and Independence-class littoral combat ships. In all honesty, shouldn't we have gotten a USS Boyington before a USS Gabrielle Giffords?