Joe Cronin gave Benjamin a tryout in mid-March; however, he was not signed, and he continued to play with the Colonels, moving back to the outfield. In 123 games played, he hit just .237, and did not hit a home run. He returned to the Baltimore Orioles of the International League for the 1944 season, which had switched its major league affiliation to the Cleveland Indians. He enjoyed a resurgence in his offensive statistics that season, as his batting average rose to .301, and he hit 24 doubles, eight triples, and 12 home runs in 133 games played. The Indians called up Benjamin for the 1945 season, and even though he was part of their regular roster, he appeared in only 14 games, batting .333. On March 26, 1946, he was released by the Cleveland Indians, and he would never appear in another major league game. In his five-season major league career, Benjamin hit .229 with five home runs and 41 RBIs in 241 games. He played for and managed the Nazareth, Pennsylvania based Nazareth Cement Dusters of the Class D North Atlantic League. He played several different positions that season, including two games at pitcher. He batted .312 and hit four home runs during his only season with the Cement Dusters. Benjamin played for several different teams in 1947, beginning the season with the Houston Buffaloes, a St. Louis Cardinals affiliate, but later joined the San Antonio Missions, a St. Louis Browns affiliate. Both teams were in the Texas League. Late in the season, the Browns promoted him to their Class AAA team, the Toledo Mud Hens of the American Association. In 1948, he played for, and managed, the Fresno Cardinals of the Class C California League, an affiliate of the St. Louis Cardinals. In 125 games played that season, he batted .326 and hit 27 doubles, five triples, and nine home runs. After the season completed, he retired as a player. Post-playing career High school athletics After his baseball playing career ended, he moved to Greenfield, Massachusetts, and became an assistant football coach at Greenfield High School, while also working as a physical education teacher at a nearby middle school. Benjamin was Greenfield's head football coach from 1958 to 1964, as well as the head baseball coach from 1948 to 1964. He coached the baseball team to several Western Massachusetts championships. Among the other duties, he also refereed