Leonard was born in Philadelphia. He was a standout in football, basketball and baseball at Overbrook High School in Philadelphia, which produced basketball stars Wilt Chamberlain and Walt Hazzard. He got 60 scholarship offers for football, five for basketball and none for baseball, where he played shortstop and twice hit two home runs in one inning.[citation needed]\n', '

Leonard was signed as an amateur free agent by the Los Angeles Dodgers in June 1973.\n', '

While playing in the minor leagues in the middle of the 1981 season Max Venable and Guy Sularz gave Jeffrey Leonard the nickname "HackMan"[citation needed] because he had a habit of swinging at the first pitch no matter what. People spelled it "Hackman" but he did not like the way the spelling looked, and said, "Spell it like the video game PacMan", so it came out as "HacMan."[citation needed] Leonard was known for his "one flap down" routine: running around the bases after hitting a home run with one arm hanging motionless at his side. Leonard tied for the California League lead for assists by an outfielder with 13 while playing for the Bakersfield Dodgers in 1976.[citation needed] He also led the Pacific Coast League in hits (183) and batting average (.365) while playing for the Albuquerque Dukes in 1978.[citation needed]\n', '

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