Bobb, a native Washingtonian and an outstanding baseball and basketball player, was the starting pitcher for Coolidge High School from 1951 to1953. In 1952-53, Bobb was 1st team all-high in baseball and one of the leading scorers on the Varsity basketball team. After graduation, Bobb was offered a signing bonus from both the Pittsburgh Pirates and the Philadelphia Phillies. Instead, he accepted a four-year baseball scholarship to the University of Maryland. Bobb was a starting pitcher on the freshman baseball team and from 1955-57, he was a starting pitcher on the varsity baseball team. In 1956, he pitched the dedication game of Shipley Field against Dartmouth, and won on a 6 hitter.