Having graduated from high school in June, 1942, Winfield, nicknamed Bud, and his friend Bob both enlisted in the Army Air Corps in Boston that year. Bud in September and Bob in December. Bud then underwent training to be a pilot and then advanced training to be a fighter pilot at Marianna Army Air Field in Florida. His active duty date is listed as December 5, 1943. He left for duty in the Pacific Theater on April 24, 1944 as a 20 year old 2nd Lieutenant with the 5th Air Force.
With his base at Clark Field in the Philippines, he saw action in New Guinea, Southern Philippines, Luzon, Okinawa, and Iwo Jima, flying 8 to 8 1/2 hours/day with the 39th Fighter Squadron. He flew the P51 Mustang, an American long range, single seat fighter and fighter-bomber and is credited with two kills. He met his wife, Lt. Allayne Forester, who had arrived as a flight nurse based at Clark Field on April 13, 1945. They dated, he named his Mustang "Miss Allayne- ious," they fell in love, and then he married her on August 5, 1945, at the Clark Field airbase, with Allayne wearing a wedding dress made by Filipino women from parachute silk. By this time, they had both been promoted to 1st Lieutenant. They married the day before the atomic bomb was dropped on Hiroshima! Bud had accumulated enough points to go home, but Allayne was scheduled for occupation of Japan after the Japanese surrendered following the Nagasaki bombing on August 9th.
Bud's departure for the United States was delayed because he suffered a bout of Dengue Fever which required hospitalization; but he finally left the Philippines on August 28, 1945 and arrived in the United States on September 14, 1945. He was honorably discharged on November 6, 1945 and spent the next 12 years in the Air Force Reserve. Bud received the Asiatic Pacific Campaign Ribbon with 4 stars, the Air Medal with 2 Oak Leaf Clusters, the Philippine Liberation Ribbon with a Bronze Star, and the Good Conduct Medal. His best friend, Bob Little, was not so lucky. Bob was shot down over Germany and never made it home.