He enlisted in the United States Army Air Forces on May 14, 1942, and entered the Aviation Cadet Program in October 1942. Drew was commissioned a 2d Lt and awarded his pilot wings in Marianna Army Field on October 1, 1943, and began training as an instructor pilot for the North American P-51 Mustang at Bartow Field and then served as a P-51 Mustang instructor pilot with the 56th Fighter Squadron of the 54th Fighter Group. He went overseas in May 1944 and was assigned to the 375th Fighter Squadron of the 361st Fighter Group, which was stationed at RAF Bottisham and later at RAF Little Walden. During his tour with the 361st Fighter Group, which was commonly known as "Yellowjackets", Drew completed 75 missions, rising to command of "A" Flight and the 375th Fighter Squadron. Drew would be officially credited with six aerial victories during his combat tour. "Detroit Miss", coded E2-D was his personal P-51, during his tour with 361st Fighter Group. He was credited with 6 aerial victories, 1 ground victory, 1 damaged and 1 water kill, in which he and his wingman sank and burned the largest aircraft in world, the Blohm & Voss BV238-V1 on 18 September 1944. Hitler was going to use it to bomb Washington and New York City.
His biggest day was on October 7, 1944, when he shot down 2 jet-powered Me 262s on a single mission while leading an attack on Achmer Aerodrome. His appeal for the Distinguished Service Cross was denied, because of the lack of evidence for his kills; the gun camera of his P-51 had jammed and his wingman, 2nd Lt. Robert McCandliss was shot down and became a prisoner of war. However, he was awarded the Air Force Cross many years later.
More than 40 years later, an Air Force clerk noticed Drew's claim for two Me 262 victories on the same mission. She contacted a custodian of German war records who knew former Luftwaffe pilots who might be able to shed light on the claim. Georg-Peter Eder had been set to lead the Me 262s of JG 7 that day, but when his aircraft had problems taking off the two-ill-fated pilots took off to lead JG 7. Eder says he saw a yellow-nosed P-51 dive on the Me 262s and shoot them down. Eder couldn't read "Detroit Miss" on the nose of the P-51 Mustang, but his account was sufficient to confirm Drew's two Me 262 victories. After the total story was confirmed by both the German Luftwaffe archives and the United States Air Force archives, the Air Force Board for the Correction of Military Records recommended that Drew and his wife were flown in an Air Force C-141 Starlifter from Johannesburg, South Africa for the ceremony. The Secretary of the Air Force, Verne Orr presented the Air Force Cross on May 12, 1983. He is one of the only three airmen to receive Air Force Cross for actions in World War II.