Benjamin was a star with Framingham High School in Massachusettes and went on to play from 1939-1942 with the Phillies and finished up his Major League career with the Indians in 1945. In 1965, Benjamin joined the Houston Astros as a scout. He remained with the Astros for nearly 40 years. He scouted American League East clubs for several seasons before becoming the team's scouting supervisor for the Northeast. Benjamin was a frequent visitor to Fenway Park during the baseball season.
Astros president Tal Smith, who was born in Framingham, called Benjamin a "vital cog" in the organization and a "keen judge of talent."