Eugene Leo played in the Golden Era of softball, primarily on the South and Southwest sides, when every neighborhood had a softball team good enough for pot games. Playing four nights a week with three games on Sunday, like many softball players of this era, Eugene Leo’s career can be divided into two segments – before and after World War Two. Before the war Leo played on the usual neighborhood teams. He won the O’Keefe Men’s League five times before and after the war. After he returned from the war, his career diversified when he played with his first Windy City team, Harry’s Owl Club. Later he formed and played shortstop on his own Windy City team, the Douglas Senators. Eugene Leo left the softball diamonds of Chicago for college in Colorado in 1949. After graduation, he returned and played for Swift and Company in the Southwest Industrial League in Gage Park. Clinching the championship in that league, they headed for the playoffs in Grant Park. They took the championship of the Greater Chicago Industrial League in 1952. Leo contributed to the championship by slugging the most home runs and maintaining the highest batting average. Eugene Leo resides in South Holland with his wife, Virginia.