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Overbrook High School (1953 – 1955)

Chamberlain stood 6 ft 11 in (2.11 m) when he entered Philadelphia's Overbrook High School. As an avid track and field athlete, he high jumped 6 feet, 6 inches, ran the 440 yards in 49.0 seconds and the 880 yards in 1:58.3, put the shot 53 feet, 4 inches, and long jumped 22 feet.

Chamberlain was the star player for the Overbrook Hilltoppers basketball team, wearing jersey number five. Chamberlain had a natural advantage against his peers; he became renowned for his scoring talent, physical strength, and shot-blocking abilities. According to ESPN journalist Hal Bock, Chamberlain was "scary, flat-out frightening... before he came along, very few players at the center position possessed his level of athleticism, stature, and stamina. Chamberlain changed the game in fundamental ways no other player did." In this period of his life, his three lifelong nicknames "Wilt the Stilt", "Goliath", and "The Big Dipper"—his favorite—were coined.

Chamberlain led the team to two city championships over three seasons, with Overbrook logging a 56–3 win-loss record. He broke Hall of Fame guard Tom Gola 's Philadelphia-high-school scoring record (2,222 points) and graduated with 2,252 points, averaging 37.4 points per game.