Dallessandro's time with the Red Sox was brief, as he played only a handful of games for them. In 1939, he was traded to the Chicago Cubs, where he spent the majority of his career. It was with the Cubs that Dallessandro found more opportunities to showcase his skills on the field. Standing at 5 feet 6 inches and weighing around 168 pounds, he was not the most physically imposing player, but he was known for his tenacity and ability to get on base.
During his tenure with the Cubs, Dallessandro became known for his consistent batting. He was a left-handed hitter, which gave him an advantage against right-handed pitchers. His best season came in 1941 when he played in 148 games and achieved a batting average of .272. That year, he also recorded 7 home runs and 85 runs batted in (RBIs), demonstrating his ability to contribute offensively to the team.
World War II interrupted many baseball careers, and Dallessandro's was no exception. Like many players of his era, his career was affected by the war, which led to a temporary decline in the level of competition in the major leagues as many players served in the military. Despite these challenges, Dallessandro continued to play for the Cubs throughout the war years.
After the war, Dallessandro's playing time began to decrease. His last season in the major leagues was in 1947. Over the course of his career, he played in 746 games, with a lifetime batting average of .267, 22 home runs, and 303 RBIs. While these numbers may not place him among the legends of the game, they reflect a solid career as a reliable player who contributed to his team's efforts over a decade.
Following his retirement from playing, Dallessandro's life after baseball is less documented.
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