LeGrande was an outfield star in the major Negro Leagues and barnstormed with one of baseball's most colorful characters, Satchel Paige. LeGrande was a 14-year-old catcher for the Webster All-Stars of the Blue Ridge when he was noticed by the Negro Leagues. He debuted with the Memphis Red Sox in 1957 and moved on to the Detroit All-Stars in 1958. The next season, LeGrande played for the Kansas City Monarchs, leading Negro League outfielders in assists for a third consecutive season. Combining speed and power, LeGrande hit over .300 in his three Negro League seasons. LeGrande signed with the New York Yankees in 1959 and led the Class A Florida State League with a .304 average for the St. Petersburg Saints in 1960. He finished his career barnstorming with Paige in 1963.