Montgomery was born on April 16, 1944, in
Nashville, Tennessee. Baseball played a huge role in his family; his father frequently took part in
sandlot ball, while his brother Gerald played for several minor league affiliates of the
Boston Red Sox. Montgomery attended Nashville's Central High School. Although he actively participated in three sports, he was most inclined to baseball, playing in the
outfield, at
first base and
pitching. Upon his graduation from high school. Montgomery was signed by
George J. Digby, a renowned scout who worked for the Boston Red Sox organization. ==Professional career==