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Gary Antonian Sheffield was November 18th, 1968 in Tampa, Florida. His mother Betty was the older sister of Dwight Gooden. Betty chose to raise Gary on her own, moving the the two of them to Belmont Heights, near the notorious Ponce de Leon projects with the Gooden’s. During his childhood, Gary and Dwight did everything together, with Dwight often hauling Gary out of bed, handing him a bat, and making him try to hit what was already a tremendous fastball for an 11-year old. Gary was well known for his temper from an early age. He had arrived late for a practice, and was subsequently benched, which Gary remedied by chasing his coach around the diamond with a bat.

When Gary was 11, he was selected to the Belmont Heights Little League All-stars, a team which included future big-leaguers Ty Griffin and Derek Bell. Their team went on a roll and made it to the Little League World Series, where they would advance all the way to the championship game, before falling to Taiwan 4-3. Gary played for Hillsborough High School’s varsity team by his sophomore year, and by junior year he’d beefed up to 175 pounds, while playing both 3rd base and pitching. During his senior year, he frequently showed home run power while commanding a fastball in the upper 80’s. As a batter, Sheffield batted .500 with 15 home runs-while not striking out once- and would win the Gatorade Player of the Year Award.