The wing came into existence on the 18th of October 1927, as the 19th Observation Group, an inactive unit of the Army Air Corps. In March 1932, the unit was activated at Rockwell Army Air Field, California and redesignated as the 19th Bomb Group. The unit remained in California until 1941 flying B-10s and B-18s. In 1941, flying the newly built B-17C long-range bomber, the 19th Bomb Group deployed to the Philippines. In route, the Group under the command of Lt. Colonel Eugene Eubanks made aviation history. For the first time ever, a mass flight of heavy bombers flew the 2,400 miles from the west coast of the United States to Hawaii. By early fall 1941, the 19th had completed deployment of personnel and equipment overseas and was now prepared to function as the long-range strike arm of the Far East Air Force.
On December 8, 1941, the 19th was caught off-guard at Clark Army Air Field, the Philippines, and was virtually destroyed by a Japanese attack. The attack destroyed most of the aircraft and seriously damaged the remaining aircraft. Despite this, the 19th Bombardment Group was the first American air unit to strike back at the Japanese.