Glen Callaway, the son of James and Mary Callaway, was born on June 3, 1919, in Holdenville, Oklahoma - about 80 miles southeast of Oklahoma City.

Glen had eight sisters and four brothers. Three of his brothers were ballplayers and played for Moss High School. Glen also played baseball at Moss, as well as basketball and competing in track. Additionally, he played for the Holdenville team in the local Ban Johnson League, and the Holdenville American Legion junior baseball team that were Oklahoma state champions in 1936.

Glen graduated from high school in 1938, and was playing with the Hulsey Community baseball team in 1939, with his brothers. Grady, known as “Hook,” was a pitcher, Edmond, known as “Bud,” was the catcher, Lenard played the outfield, and Glen played third base.

In 1940, the 20-year-old signed with the Muskogee Reds of the Class C Western Association. The Reds were managed by Jack Mealy, who was also from Holdenville, and had been a catcher in the minors since 1922. Even at the age of 40 in 1940, he played over 70 games behind the plate.

Callaway was released early in the season by Muskogee, but was soon picked up in May 1940 by the Fayetteville Angels of the Class D Arkansas-Missouri League – a Brooklyn Dodgers farm team. Although stats are incomplete for the league, Callaway appeared in at least 21 games and was batting over .340 when the four-team league folded.

Brooklyn sent the youngster to the Newport Dodgers of the Class D Northeast Arkansas League, where he finished the season appearing in a further 51 gams and batted .230.

In 1941, Brooklyn assigned Callaway to the Big Spring Bombers of the Class D West Texas-New Mexico League, where he played a handful of games before being released. The following month he was back in Holdenville, playing for the local team before joining the National Guard. Callaway married the former Helen Story in March 1942, and their son Bobby was born in November of that year.

After 18 months in the National Guard, Glen enlisted with the Army in October 1942. He served with the 350th Infantry Regiment, 88th Infantry Division, and trained with the medical detachment at Camp Gruber, Oklahoma, and Fort Sam Houston, Texas. He went overseas in December 1943, and was in frontline action in Italy as a litter bearer from January 1944. A litter bearer was a frontline medic responsible for carrying wounded soldiers on stretchers ("litters") from the battlefield to aid stations. It was one of the most dangerous roles in combat - often under fire, unarmed, and driven by sheer courage and compassion. Glen Callaway’s service in this role speaks volumes about his character.

Technician Fourth Grade Callaway was killed in action July 10, 1944, near Villamagna, during the US Fifth Army’s push towards the River Arno.

Glan Callaway’s remains were returned to Holdenville in June 1949, with funeral services at the First Baptist Church and burial at Holdenville Cemetery on July 1, 1949.

Glen’s younger brother, Grady, signed with the Ada Herefords of the Class D Sooner State League in March 1947, but did not appear in a regular season game.