After growing up in North Carolina, he played for the Homestead Grays between 1934 and 1950, batting fourth behind Josh Gibson for many years.
Late in life, Leonard worked as a physical education instructor and was the vice-president of a minor league baseball team.
[4] When Leonard was about seven years old, he would sneak over to the baseball field of the local white team and watch games through the fence.
There was no black high school in Rocky Mount, so Leonard finished the eighth grade and went to work shining shoes for a rail station.
[7] He began his Negro league career in 1933 with the Brooklyn Royal Giants, then moved to the legendary Homestead Grays in 1934, the team he played for until his retirement in 1950.
In 1952, Leonard was offered a major league contract, but he believed that at age 45 he was too old and might embarrass himself and hurt the cause of integration.
[12] In 1953, Leonard made his only appearances in "organized" ball, playing for the unaffiliated Portsmouth Merrimacs of the class B Piedmont League, hitting .333 in 10 games and 46 at bats.
[13] After retiring as a player, Leonard worked as a truant officer, served as a physical education instructor and started a realty company.
At his induction ceremony on August 7 of that year, Leonard said, "We in the Negro leagues felt like we were contributing something to baseball, too, when we were playing.
[7] In 1994, the Major League Baseball All-Star Game was held in Pittsburgh, hometown of the Grays, and the 88-year-old Leonard was named an honorary captain.
Shortly before his death in 1997, Leonard was the subject of a North Carolina General Assembly proclamation recognizing his contributions to baseball.
Leonard's contemporaries, including catcher Roy Campanella and pitcher Dave Barnhill, cited his quick bat as one of his greatest strengths.
[15] The first results from this study were the statistics for Negro league Hall of Famers elected prior to 2006, which were published in Shades of Glory by Lawrence D. Hogan.